# Supplementary Information (SI) for Reaction Chemistry & Engineering.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 2434027'
loop_
_audit_author_name
_audit_author_address
'Simon Lawrence'
;University College Cork
Ireland
;
_audit_update_record             
;
2025-03-25 deposited with the CCDC.	2025-05-09 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C16 H14 Cl N O S'
_chemical_formula_sum            'C16 H14 Cl N O S'
_chemical_formula_iupac          ?
_chemical_formula_weight         303.79

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.7393(7)
_cell_length_b                   5.9359(4)
_cell_length_c                   21.5347(13)
_cell_angle_alpha                90
_cell_angle_beta                 92.636(2)
_cell_angle_gamma                90
_cell_volume                     1499.02(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9990
_cell_measurement_theta_min      5.4514
_cell_measurement_theta_max      67.1313
_cell_measurement_temperature    296.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_size_max          0.257
_exptl_crystal_size_mid          0.212
_exptl_crystal_size_min          0.176
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             632

_exptl_absorpt_coefficient_mu    3.505
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.54
_exptl_absorpt_correction_T_max  0.75

_exptl_special_details           
;
;

_diffrn_ambient_temperature      296.(2)

_diffrn_source                   'Incoatec Microfocus X-ray Source I\mS'
_diffrn_source_type              Microfocus

_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'Incoatec Montel Multilayer Mirror'

_diffrn_measurement_device_type  'Bruker ACS Kappa APEX II DUO diffractometer'
_diffrn_measurement_method       'ω and φ scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            18151
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_av_unetI/netI     0.0189
_diffrn_reflns_theta_min         7.09
_diffrn_reflns_theta_max         67.19
_diffrn_reflns_theta_full        67.19
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measured_fraction_theta_full 0.968
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25

_refine_special_details          
;
;

_reflns_number_total             2592
_reflns_number_gt                2545
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0367
_refine_ls_wR_factor_gt          0.1011
_refine_ls_wR_factor_ref         0.1016
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_restrained_S_all      1.106
_refine_ls_number_reflns         2592
_refine_ls_number_parameters     186
_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)+(0.0550P)²+0.4620P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.294
_refine_diff_density_min         -0.277
_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'
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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'Bruker Instrument Service v2013.12.0.0'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_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
C C1 0.15662(14) 0.5858(3) 0.52772(8) 0.0443(4) Uani d . . . 1 . .
C C2 0.18031(13) 0.6193(3) 0.59651(7) 0.0402(4) Uani d . . . 1 . .
C C3 0.15106(15) 0.4512(3) 0.63307(8) 0.0469(4) Uani d . . . 1 . .
H H3 0.1144 0.3278 0.6145 0.056 Uiso calc U . R 1 . .
O O4 0.14478(15) 0.3963(2) 0.50645(6) 0.0670(4) Uani d . . . 1 . .
N N5 0.14985(12) 0.7765(3) 0.49397(6) 0.0447(3) Uani d . . . 1 . .
H H5 0.1570(16) 0.897(3) 0.5116(9) 0.042(5) Uiso d . . . 1 . .
C C6 0.12722(13) 0.7973(3) 0.42900(7) 0.0413(4) Uani d . . . 1 . .
C C7 0.15436(16) 0.6306(3) 0.38708(9) 0.0514(4) Uani d . . . 1 . .
H H7 0.1856 0.4946 0.401 0.062 Uiso calc U . R 1 . .
C C8 0.13415(18) 0.6699(4) 0.32386(9) 0.0590(5) Uani d . . . 1 . .
H H8 0.1522 0.5576 0.2959 0.071 Uiso calc U . R 1 . .
C C9 0.08823(17) 0.8695(4) 0.30102(9) 0.0567(5) Uani d . . . 1 . .
C C10 0.06212(16) 1.0329(3) 0.34390(9) 0.0538(5) Uani d . . . 1 . .
H H10 0.0309 1.1688 0.33 0.065 Uiso calc U . R 1 . .
C C11 0.08138(15) 0.9985(3) 0.40713(8) 0.0470(4) Uani d . . . 1 . .
H H11 0.0634 1.1113 0.435 0.056 Uiso calc U . R 1 . .
C C12 0.0654(3) 0.9087(5) 0.23232(11) 0.0869(8) Uani d . . . 1 . .
H H12A 0.1074 0.801 0.2092 0.13 Uiso calc U . R 1 . .
H H12B 0.0889 1.0583 0.2218 0.13 Uiso calc U . R 1 . .
H H12C -0.0147 0.8916 0.2222 0.13 Uiso calc U . R 1 . .
S S13 0.23476(4) 0.87497(7) 0.62690(2) 0.04516(16) Uani d . . . 1 . .
C C14 0.37819(14) 0.8738(3) 0.60390(7) 0.0426(4) Uani d . . . 1 . .
C C15 0.44049(19) 1.0671(4) 0.61769(12) 0.0684(6) Uani d . . . 1 . .
H H15 0.4066 1.1888 0.6368 0.082 Uiso calc U . R 1 . .
C C16 0.5533(2) 1.0772(5) 0.60278(15) 0.0875(8) Uani d . . . 1 . .
H H16 0.5954 1.2063 0.6124 0.105 Uiso calc U . R 1 . .
C C17 0.60440(19) 0.9005(5) 0.57409(13) 0.0786(7) Uani d . . . 1 . .
H H17 0.6802 0.9105 0.5636 0.094 Uiso calc U . R 1 . .
C C18 0.54279(18) 0.7090(5) 0.56105(10) 0.0680(6) Uani d . . . 1 . .
H H18 0.5772 0.5881 0.5418 0.082 Uiso calc U . R 1 . .
C C19 0.42991(15) 0.6942(4) 0.57624(8) 0.0528(4) Uani d . . . 1 . .
H H19 0.3889 0.5628 0.5678 0.063 Uiso calc U . R 1 . .
Cl Cl20 0.17592(5) 0.44527(10) 0.71161(2) 0.0703(2) Uani 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
C1 O4 . 1.220(2) ?
C1 N5 . 1.346(2) ?
C1 C2 . 1.508(2) ?
C2 C3 . 1.326(2) ?
C2 S13 . 1.7612(16) ?
C3 Cl20 . 1.7034(18) ?
C3 H3 . 0.93 ?
N5 C6 . 1.417(2) ?
N5 H5 . 0.81(2) ?
C6 C11 . 1.384(3) ?
C6 C7 . 1.386(2) ?
C7 C8 . 1.391(3) ?
C7 H7 . 0.93 ?
C8 C9 . 1.383(3) ?
C8 H8 . 0.93 ?
C9 C10 . 1.383(3) ?
C9 C12 . 1.509(3) ?
C10 C11 . 1.385(3) ?
C10 H10 . 0.93 ?
C11 H11 . 0.93 ?
C12 H12A . 0.96 ?
C12 H12B . 0.96 ?
C12 H12C . 0.96 ?
S13 C14 . 1.7769(18) ?
C14 C19 . 1.376(3) ?
C14 C15 . 1.385(3) ?
C15 C16 . 1.378(4) ?
C15 H15 . 0.93 ?
C16 C17 . 1.370(4) ?
C16 H16 . 0.93 ?
C17 C18 . 1.369(3) ?
C17 H17 . 0.93 ?
C18 C19 . 1.382(3) ?
C18 H18 . 0.93 ?
C19 H19 . 0.93 ?

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
O4 C1 N5 . . 124.76(16) ?
O4 C1 C2 . . 120.21(16) ?
N5 C1 C2 . . 115.03(14) ?
C3 C2 C1 . . 116.29(15) ?
C3 C2 S13 . . 121.82(13) ?
C1 C2 S13 . . 121.75(12) ?
C2 C3 Cl20 . . 124.60(14) ?
C2 C3 H3 . . 117.7 ?
Cl20 C3 H3 . . 117.7 ?
C1 N5 C6 . . 127.58(15) ?
C1 N5 H5 . . 119.0(14) ?
C6 N5 H5 . . 113.4(14) ?
C11 C6 C7 . . 119.47(16) ?
C11 C6 N5 . . 117.60(15) ?
C7 C6 N5 . . 122.85(16) ?
C6 C7 C8 . . 118.92(18) ?
C6 C7 H7 . . 120.5 ?
C8 C7 H7 . . 120.5 ?
C9 C8 C7 . . 122.56(18) ?
C9 C8 H8 . . 118.7 ?
C7 C8 H8 . . 118.7 ?
C8 C9 C10 . . 117.27(17) ?
C8 C9 C12 . . 122.0(2) ?
C10 C9 C12 . . 120.8(2) ?
C9 C10 C11 . . 121.47(19) ?
C9 C10 H10 . . 119.3 ?
C11 C10 H10 . . 119.3 ?
C6 C11 C10 . . 120.33(17) ?
C6 C11 H11 . . 119.8 ?
C10 C11 H11 . . 119.8 ?
C9 C12 H12A . . 109.5 ?
C9 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C9 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
C2 S13 C14 . . 103.03(8) ?
C19 C14 C15 . . 119.70(18) ?
C19 C14 S13 . . 124.48(13) ?
C15 C14 S13 . . 115.77(16) ?
C16 C15 C14 . . 119.3(2) ?
C16 C15 H15 . . 120.4 ?
C14 C15 H15 . . 120.4 ?
C17 C16 C15 . . 121.2(2) ?
C17 C16 H16 . . 119.4 ?
C15 C16 H16 . . 119.4 ?
C18 C17 C16 . . 119.3(2) ?
C18 C17 H17 . . 120.3 ?
C16 C17 H17 . . 120.3 ?
C17 C18 C19 . . 120.5(2) ?
C17 C18 H18 . . 119.8 ?
C19 C18 H18 . . 119.8 ?
C14 C19 C18 . . 119.99(19) ?
C14 C19 H19 . . 120.0 ?
C18 C19 H19 . . 120.0 ?

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
O4 C1 C2 C3 . . . . -21.3(2) ?
N5 C1 C2 C3 . . . . 158.51(16) ?
O4 C1 C2 S13 . . . . 162.89(15) ?
N5 C1 C2 S13 . . . . -17.3(2) ?
C1 C2 C3 Cl20 . . . . 176.61(13) ?
S13 C2 C3 Cl20 . . . . -7.6(2) ?
O4 C1 N5 C6 . . . . 0.7(3) ?
C2 C1 N5 C6 . . . . -179.12(14) ?
C1 N5 C6 C11 . . . . 155.66(17) ?
C1 N5 C6 C7 . . . . -27.7(3) ?
C11 C6 C7 C8 . . . . -0.3(3) ?
N5 C6 C7 C8 . . . . -176.87(16) ?
C6 C7 C8 C9 . . . . 0.2(3) ?
C7 C8 C9 C10 . . . . -0.1(3) ?
C7 C8 C9 C12 . . . . -179.2(2) ?
C8 C9 C10 C11 . . . . 0.2(3) ?
C12 C9 C10 C11 . . . . 179.27(19) ?
C7 C6 C11 C10 . . . . 0.4(2) ?
N5 C6 C11 C10 . . . . 177.11(15) ?
C9 C10 C11 C6 . . . . -0.3(3) ?
C3 C2 S13 C14 . . . . 112.62(15) ?
C1 C2 S13 C14 . . . . -71.80(14) ?
C2 S13 C14 C19 . . . . -7.34(17) ?
C2 S13 C14 C15 . . . . 175.17(15) ?
C19 C14 C15 C16 . . . . 0.7(3) ?
S13 C14 C15 C16 . . . . 178.4(2) ?
C14 C15 C16 C17 . . . . 0.6(4) ?
C15 C16 C17 C18 . . . . -1.2(4) ?
C16 C17 C18 C19 . . . . 0.4(4) ?
C15 C14 C19 C18 . . . . -1.5(3) ?
S13 C14 C19 C18 . . . . -178.89(15) ?
C17 C18 C19 C14 . . . . 0.9(3) ?

####################################################################### 
# 
# 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_I_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2434028'
loop_
_audit_author_name
_audit_author_address
'Simon Lawrence'
;University College Cork
Ireland
;
_audit_update_record             
;
2025-03-25 deposited with the CCDC.	2025-05-09 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C16 H14 Cl N O S'
_chemical_formula_sum            'C16 H14 Cl N O S'
_chemical_formula_iupac          ?
_chemical_formula_weight         303.79

_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                   11.0845(3)
_cell_length_b                   9.0521(2)
_cell_length_c                   15.9379(4)
_cell_angle_alpha                90
_cell_angle_beta                 98.0480(10)
_cell_angle_gamma                90
_cell_volume                     1583.43(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9976
_cell_measurement_theta_min      4.5740
_cell_measurement_theta_max      67.2979
_cell_measurement_temperature    296.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_size_max          0.422
_exptl_crystal_size_mid          0.296
_exptl_crystal_size_min          0.227
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             632

_exptl_absorpt_coefficient_mu    3.318
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.61
_exptl_absorpt_correction_T_max  0.75

_exptl_special_details           
;
;

_diffrn_ambient_temperature      296.(2)

_diffrn_source                   'Incoatec Microfocus X-ray Source I\mS'
_diffrn_source_type              Microfocus

_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'Incoatec Montel Multilayer Mirror'

_diffrn_measurement_device_type  'Bruker ACS Kappa APEX II DUO diffractometer'
_diffrn_measurement_method       'ω and φ scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            19374
_diffrn_reflns_av_R_equivalents  0.0249
_diffrn_reflns_av_unetI/netI     0.0138
_diffrn_reflns_theta_min         5.63
_diffrn_reflns_theta_max         67.29
_diffrn_reflns_theta_full        67.29
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measured_fraction_theta_full 0.960
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       18

_refine_special_details          
;
;

_reflns_number_total             2728
_reflns_number_gt                2599
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0547
_refine_ls_R_factor_gt           0.0533
_refine_ls_wR_factor_gt          0.1497
_refine_ls_wR_factor_ref         0.1511
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_restrained_S_all      1.240
_refine_ls_number_reflns         2728
_refine_ls_number_parameters     186
_refine_ls_number_restraints     36
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0771P)²+0.9909P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.614
_refine_diff_density_min         -0.256
_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'
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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'Bruker Instrument Service v2013.12.0.0'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_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
C C1 0.4739(2) 0.7060(2) 0.78798(15) 0.0494(6) Uani d . . . 1 . .
C C2 0.5561(2) 0.6293(3) 0.85852(15) 0.0530(6) Uani d . . . 1 . .
C C3 0.5281(2) 0.5070(3) 0.89681(15) 0.0527(6) Uani d . . . 1 . .
H H3 0.5869 0.4662 0.9375 0.063 Uiso calc U . R 1 . .
O O4 0.44499(18) 0.83515(18) 0.79484(11) 0.0602(5) Uani d . . . 1 . .
N N5 0.4387(2) 0.6221(2) 0.71972(13) 0.0552(5) Uani d . . . 1 . .
H H5 0.468(2) 0.544(3) 0.7218(17) 0.047(7) Uiso d . . . 1 . .
C C6 0.3632(2) 0.6689(3) 0.64514(16) 0.0539(6) Uani d . . . 1 . .
C C7 0.3935(3) 0.6264(3) 0.56758(17) 0.0672(7) Uani d . . . 1 . .
H H7 0.4617 0.5676 0.5651 0.081 Uiso calc U . R 1 . .
C C8 0.3226(3) 0.6712(4) 0.49350(19) 0.0782(9) Uani d . . . 1 . .
H H8 0.3443 0.6423 0.4416 0.094 Uiso calc U . R 1 . .
C C9 0.2208(3) 0.7574(4) 0.4950(2) 0.0786(9) Uani d . . . 1 . .
C C10 0.1919(3) 0.7989(4) 0.5731(2) 0.0778(9) Uani d . . . 1 . .
H H10 0.124 0.8583 0.5754 0.093 Uiso calc U . R 1 . .
C C11 0.2613(3) 0.7548(3) 0.64847(19) 0.0650(7) Uani d . . . 1 . .
H H11 0.2392 0.7828 0.7004 0.078 Uiso calc U . R 1 . .
C C12 0.1449(4) 0.8073(6) 0.4136(3) 0.1149(15) Uani d U . . 1 . .
H H12A 0.1975 0.8416 0.3748 0.172 Uiso calc U . R 1 . .
H H12B 0.0919 0.8861 0.4257 0.172 Uiso calc U . R 1 . .
H H12C 0.0969 0.726 0.3888 0.172 Uiso calc U . R 1 . .
S S13 0.69078(8) 0.72032(10) 0.90126(6) 0.0804(3) Uani d . . . 1 . .
C C14 0.7688(3) 0.7356(3) 0.8119(2) 0.0727(8) Uani d U . . 1 . .
C C15 0.8448(3) 0.8566(4) 0.8074(3) 0.0911(11) Uani d U . . 1 . .
H H15 0.8517 0.9296 0.8489 0.109 Uiso calc U . R 1 . .
C C16 0.9105(4) 0.8656(6) 0.7387(3) 0.1054(13) Uani d U . . 1 . .
H H16 0.9636 0.9444 0.7359 0.126 Uiso calc U . R 1 . .
C C17 0.8994(4) 0.7663(7) 0.6783(4) 0.1189(15) Uani d U . . 1 . .
H H17 0.9428 0.7776 0.6328 0.143 Uiso calc U . R 1 . .
C C18 0.8243(4) 0.6448(5) 0.6810(3) 0.1026(12) Uani d U . . 1 . .
H H18 0.8171 0.5744 0.6381 0.123 Uiso calc U . R 1 . .
C C19 0.7602(3) 0.6304(4) 0.7490(2) 0.0809(9) Uani d . . . 1 . .
H H19 0.7105 0.5484 0.7523 0.097 Uiso calc U . R 1 . .
Cl Cl20 0.39050(6) 0.41908(8) 0.87629(4) 0.0645(3) Uani 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
C1 O4 . 1.221(3) ?
C1 N5 . 1.340(3) ?
C1 C2 . 1.513(3) ?
C2 C3 . 1.322(4) ?
C2 S13 . 1.757(3) ?
C3 Cl20 . 1.711(3) ?
C3 H3 . 0.93 ?
N5 C6 . 1.420(3) ?
N5 H5 . 0.77(3) ?
C6 C11 . 1.378(4) ?
C6 C7 . 1.381(4) ?
C7 C8 . 1.384(4) ?
C7 H7 . 0.93 ?
C8 C9 . 1.375(5) ?
C8 H8 . 0.93 ?
C9 C10 . 1.380(5) ?
C9 C12 . 1.513(5) ?
C10 C11 . 1.391(4) ?
C10 H10 . 0.93 ?
C11 H11 . 0.93 ?
C12 H12A . 0.96 ?
C12 H12B . 0.96 ?
C12 H12C . 0.96 ?
S13 C14 . 1.773(4) ?
C14 C19 . 1.376(5) ?
C14 C15 . 1.390(5) ?
C15 C16 . 1.400(6) ?
C15 H15 . 0.93 ?
C16 C17 . 1.311(7) ?
C16 H16 . 0.93 ?
C17 C18 . 1.384(7) ?
C17 H17 . 0.93 ?
C18 C19 . 1.383(5) ?
C18 H18 . 0.93 ?
C19 H19 . 0.93 ?

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
O4 C1 N5 . . 124.4(2) ?
O4 C1 C2 . . 120.7(2) ?
N5 C1 C2 . . 114.8(2) ?
C3 C2 C1 . . 124.8(2) ?
C3 C2 S13 . . 117.1(2) ?
C1 C2 S13 . . 117.60(18) ?
C2 C3 Cl20 . . 124.2(2) ?
C2 C3 H3 . . 117.9 ?
Cl20 C3 H3 . . 117.9 ?
C1 N5 C6 . . 125.5(2) ?
C1 N5 H5 . . 114.(2) ?
C6 N5 H5 . . 120.(2) ?
C11 C6 C7 . . 119.7(3) ?
C11 C6 N5 . . 121.8(2) ?
C7 C6 N5 . . 118.5(3) ?
C6 C7 C8 . . 120.1(3) ?
C6 C7 H7 . . 120.0 ?
C8 C7 H7 . . 120.0 ?
C9 C8 C7 . . 121.4(3) ?
C9 C8 H8 . . 119.3 ?
C7 C8 H8 . . 119.3 ?
C8 C9 C10 . . 117.7(3) ?
C8 C9 C12 . . 121.0(4) ?
C10 C9 C12 . . 121.3(4) ?
C9 C10 C11 . . 122.0(3) ?
C9 C10 H10 . . 119.0 ?
C11 C10 H10 . . 119.0 ?
C6 C11 C10 . . 119.0(3) ?
C6 C11 H11 . . 120.5 ?
C10 C11 H11 . . 120.5 ?
C9 C12 H12A . . 109.5 ?
C9 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C9 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
C2 S13 C14 . . 102.05(14) ?
C19 C14 C15 . . 119.3(4) ?
C19 C14 S13 . . 122.6(2) ?
C15 C14 S13 . . 118.0(3) ?
C14 C15 C16 . . 118.1(4) ?
C14 C15 H15 . . 121.0 ?
C16 C15 H15 . . 121.0 ?
C17 C16 C15 . . 122.0(4) ?
C17 C16 H16 . . 119.0 ?
C15 C16 H16 . . 119.0 ?
C16 C17 C18 . . 121.1(5) ?
C16 C17 H17 . . 119.4 ?
C18 C17 H17 . . 119.4 ?
C19 C18 C17 . . 118.5(5) ?
C19 C18 H18 . . 120.7 ?
C17 C18 H18 . . 120.7 ?
C14 C19 C18 . . 121.0(4) ?
C14 C19 H19 . . 119.5 ?
C18 C19 H19 . . 119.5 ?

