# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2370999'
loop_
_audit_author_name
_audit_author_address
'MADAN SAU'
;NIT Jamshedpur
India
;
_audit_update_record             
;
2024-07-15 deposited with the CCDC.	2025-08-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H18 N2 S2'
_chemical_formula_weight         410.55

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'
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/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                   10.6819(9)
_cell_length_b                   15.6337(15)
_cell_length_c                   12.8651(11)
_cell_angle_alpha                90
_cell_angle_beta                 104.783(9)
_cell_angle_gamma                90
_cell_volume                     2077.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    2961
_cell_measurement_theta_min      3.1300
_cell_measurement_theta_max      25.9530

_exptl_crystal_description       'NEEDLE SHAPE'
_exptl_crystal_colour            YELLOW
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_F_000             856
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.125
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.270
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.55333
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.69a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, EosS2'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean 8.0303
_diffrn_reflns_number            11079
_diffrn_reflns_av_unetI/netI     0.0699
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.972
_diffrn_reflns_theta_max         29.148
_diffrn_reflns_theta_full        25.500
_diffrn_measured_fraction_theta_max 0.871
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.871
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.871
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4881
_reflns_number_gt                2503
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0401P)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         4881
_refine_ls_number_parameters     263
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1320
_refine_ls_R_factor_gt           0.0591
_refine_ls_wR_factor_ref         0.1211
_refine_ls_wR_factor_gt          0.0979
_refine_ls_goodness_of_fit_ref   0.990
_refine_ls_restrained_S_all      0.990
_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
S1 S 0.66265(6) 0.44463(4) 0.43578(5) 0.0689(2) Uani 1 1 d . . . . .
S2 S 0.40537(6) 0.30974(5) 0.39998(5) 0.0701(2) Uani 1 1 d . . . . .
N1 N 0.7539(2) 0.46338(13) 0.69204(16) 0.0670(6) Uani 1 1 d . . . . .
N2 N 0.39623(18) 0.26750(14) 0.64243(16) 0.0651(6) Uani 1 1 d . . . . .
C11 C 0.4989(2) 0.34615(15) 0.52113(17) 0.0515(6) Uani 1 1 d . . . . .
C10 C 0.4800(2) 0.31990(16) 0.62364(18) 0.0550(6) Uani 1 1 d . . . . .
C7 C 0.6001(2) 0.40109(14) 0.53493(17) 0.0503(6) Uani 1 1 d . . . . .
C8 C 0.6566(2) 0.41626(16) 0.64786(19) 0.0566(6) Uani 1 1 d . . . . .
C9 C 0.5853(2) 0.36119(16) 0.71193(18) 0.0598(7) Uani 1 1 d . . . . .
C1 C 0.7833(2) 0.51067(15) 0.5139(2) 0.0598(6) Uani 1 1 d . . . . .
C20 C 0.7231(2) 0.22899(18) 0.69935(19) 0.0612(7) Uani 1 1 d . . . . .
C17 C 0.3128(2) 0.22460(17) 0.5557(2) 0.0635(7) Uani 1 1 d . . . . .
C12 C 0.3063(2) 0.23681(16) 0.4461(2) 0.0626(7) Uani 1 1 d . . . . .
C6 C 0.8157(2) 0.51152(16) 0.6263(2) 0.0635(7) Uani 1 1 d . . . . .
C19 C 0.6779(2) 0.29062(17) 0.77235(19) 0.0691(7) Uani 1 1 d . . . . .
H19A H 0.753006 0.317724 0.819296 0.083 Uiso 1 1 calc R U . . .
H19B H 0.633999 0.258652 0.817230 0.083 Uiso 1 1 calc R U . . .
C25 C 0.8268(2) 0.24824(17) 0.6570(2) 0.0738(8) Uani 1 1 d . . . . .
H25 H 0.871302 0.299400 0.675701 0.089 Uiso 1 1 calc R U . . .
C21 C 0.6612(2) 0.1522(2) 0.6700(2) 0.0738(8) Uani 1 1 d . . . . .
H21 H 0.590884 0.138014 0.696829 0.089 Uiso 1 1 calc R U . . .
C18 C 0.5326(2) 0.41377(17) 0.79257(19) 0.0784(8) Uani 1 1 d . . . . .
H18A H 0.470149 0.454333 0.754325 0.118 Uiso 1 1 calc R U . . .
H18B H 0.602590 0.443619 0.840469 0.118 Uiso 1 1 calc R U . . .
H18C H 0.492112 0.376157 0.833226 0.118 Uiso 1 1 calc R U . . .
C2 C 0.8495(3) 0.56275(17) 0.4577(2) 0.0765(8) Uani 1 1 d . . . . .
H2 H 0.826587 0.562426 0.382931 0.092 Uiso 1 1 calc R U . . .
C5 C 0.9170(3) 0.56436(19) 0.6785(3) 0.0839(9) Uani 1 1 d . . . . .
H5 H 0.941037 0.565592 0.753251 0.101 Uiso 1 1 calc R U . . .
C16 C 0.2311(3) 0.16334(19) 0.5818(3) 0.0832(8) Uani 1 1 d . . . . .
H16 H 0.233690 0.153750 0.653697 0.100 Uiso 1 1 calc R U . . .
C23 C 0.8015(3) 0.1164(2) 0.5598(2) 0.0872(9) Uani 1 1 d . . . . .
H23 H 0.827212 0.079110 0.512870 0.105 Uiso 1 1 calc R U . . .
C22 C 0.6999(3) 0.09561(19) 0.6019(3) 0.0852(9) Uani 1 1 d . . . . .
H22 H 0.657264 0.043646 0.584725 0.102 Uiso 1 1 calc R U . . .
C13 C 0.2207(3) 0.18982(19) 0.3673(2) 0.0850(9) Uani 1 1 d . . . . .
H13 H 0.217482 0.198491 0.295163 0.102 Uiso 1 1 calc R U . . .
C24 C 0.8653(3) 0.1927(2) 0.5875(3) 0.0884(9) Uani 1 1 d . . . . .
H24 H 0.934485 0.206930 0.559299 0.106 Uiso 1 1 calc R U . . .
C4 C 0.9828(3) 0.6150(2) 0.6222(4) 0.1004(11) Uani 1 1 d . . . . .
H4 H 1.050599 0.649520 0.659035 0.120 Uiso 1 1 calc R U . . .
C3 C 0.9482(3) 0.61441(19) 0.5124(3) 0.0958(10) Uani 1 1 d . . . . .
H3 H 0.991814 0.649172 0.474556 0.115 Uiso 1 1 calc R U . . .
C14 C 0.1406(3) 0.1303(2) 0.3963(3) 0.1018(11) Uani 1 1 d . . . . .
H14 H 0.082345 0.099323 0.343636 0.122 Uiso 1 1 calc R U . . .
C15 C 0.1468(3) 0.1167(2) 0.5036(4) 0.0993(11) Uani 1 1 d . . . . .
H15 H 0.093719 0.075837 0.523081 0.119 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
S1 C7 1.724(2) . ?
S1 C1 1.754(2) . ?
S2 C11 1.719(2) . ?
S2 C12 1.759(3) . ?
N1 C8 1.282(3) . ?
N1 C6 1.415(3) . ?
N2 C10 1.281(3) . ?
N2 C17 1.408(3) . ?
C11 C7 1.357(3) . ?
C11 C10 1.444(3) . ?
C10 C9 1.523(3) . ?
C7 C8 1.443(3) . ?
C8 C9 1.523(3) . ?
C9 C18 1.539(3) . ?
C9 C19 1.551(3) . ?
C1 C2 1.395(3) . ?
C1 C6 1.398(3) . ?
C20 C21 1.376(3) . ?
C20 C25 1.387(3) . ?
C20 C19 1.508(3) . ?
C17 C16 1.393(3) . ?
C17 C12 1.408(3) . ?
C12 C13 1.389(3) . ?
C6 C5 1.391(3) . ?
C25 C24 1.382(4) . ?
C21 C22 1.381(4) . ?
C2 C3 1.371(4) . ?
C5 C4 1.380(4) . ?
C16 C15 1.376(4) . ?
C23 C22 1.370(4) . ?
C23 C24 1.374(4) . ?
C13 C14 1.379(4) . ?
C4 C3 1.366(4) . ?
C14 C15 1.382(4) . ?

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 S1 C1 100.08(12) . . ?
C11 S2 C12 99.75(12) . . ?
C8 N1 C6 119.3(2) . . ?
C10 N2 C17 119.1(2) . . ?
C7 C11 C10 110.7(2) . . ?
C7 C11 S2 125.97(18) . . ?
C10 C11 S2 123.36(18) . . ?
N2 C10 C11 128.4(2) . . ?
N2 C10 C9 123.3(2) . . ?
C11 C10 C9 108.2(2) . . ?
C11 C7 C8 110.5(2) . . ?
C11 C7 S1 126.84(18) . . ?
C8 C7 S1 122.60(19) . . ?
N1 C8 C7 128.6(2) . . ?
N1 C8 C9 123.0(2) . . ?
C7 C8 C9 108.3(2) . . ?
C8 C9 C10 102.23(19) . . ?
C8 C9 C18 112.5(2) . . ?
C10 C9 C18 113.67(18) . . ?
C8 C9 C19 109.30(18) . . ?
C10 C9 C19 109.1(2) . . ?
C18 C9 C19 109.77(19) . . ?
C2 C1 C6 120.4(2) . . ?
C2 C1 S1 116.2(2) . . ?
C6 C1 S1 123.4(2) . . ?
C21 C20 C25 117.2(3) . . ?
C21 C20 C19 121.4(2) . . ?
C25 C20 C19 121.4(3) . . ?
C16 C17 N2 116.4(3) . . ?
C16 C17 C12 117.5(3) . . ?
N2 C17 C12 126.1(2) . . ?
C13 C12 C17 121.0(2) . . ?
C13 C12 S2 116.0(2) . . ?
C17 C12 S2 123.1(2) . . ?
C5 C6 C1 117.5(3) . . ?
C5 C6 N1 116.8(3) . . ?
C1 C6 N1 125.7(2) . . ?
C20 C19 C9 113.99(19) . . ?
C24 C25 C20 121.1(3) . . ?
C20 C21 C22 122.2(3) . . ?
C3 C2 C1 120.2(3) . . ?
C4 C5 C6 121.7(3) . . ?
C15 C16 C17 121.4(3) . . ?
C22 C23 C24 119.6(3) . . ?
C23 C22 C21 119.6(3) . . ?
C14 C13 C12 119.9(3) . . ?
C23 C24 C25 120.2(3) . . ?
C3 C4 C5 119.9(3) . . ?
C4 C3 C2 120.3(3) . . ?
C13 C14 C15 119.9(3) . . ?
C16 C15 C14 120.3(3) . . ?

_refine_diff_density_max         0.225
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.036

####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2463067'
loop_
_audit_author_name
_audit_author_address
'Tapas Das'
;National Institute of Technology Jamshedpur
India
;
_audit_update_record             
;
2025-06-10 deposited with the CCDC.	2025-08-21 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            'C18 H20 Cl N O2'
_chemical_formula_weight         317.80

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'
Cl Cl 0.1484 0.1585 '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'

_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                   9.0144(5)
_cell_length_b                   18.2455(9)
_cell_length_c                   10.1329(5)
_cell_angle_alpha                90
_cell_angle_beta                 94.613(4)
_cell_angle_gamma                90
_cell_volume                     1661.18(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6129
_cell_measurement_theta_min      2.2330
_cell_measurement_theta_max      26.312

_exptl_crystal_description       'Rectangular bar'
_exptl_crystal_colour            'Pale yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_F_000             672
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.09
_exptl_absorpt_coefficient_mu    0.236
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.51796
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.89a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro II AFC12 (RINC): Kappa single'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            13550
_diffrn_reflns_av_unetI/netI     0.0408
_diffrn_reflns_av_R_equivalents  0.0433
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.232
_diffrn_reflns_theta_max         27.037
_diffrn_reflns_theta_full        25.500
_diffrn_measured_fraction_theta_max 0.944
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.944
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.944
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             3435
_reflns_number_gt                2273
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0557P)²+0.1576P] 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     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0096(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3435
_refine_ls_number_parameters     201
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0747
_refine_ls_R_factor_gt           0.0485
_refine_ls_wR_factor_ref         0.1388
_refine_ls_wR_factor_gt          0.1270
_refine_ls_goodness_of_fit_ref   1.114
_refine_ls_restrained_S_all      1.114
_refine_ls_shift/su_max          0.004
_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
Cl22 Cl 0.58530(9) 0.61507(4) 0.34119(7) 0.1099(3) Uani 1 1 d . . . . .
O20 O 0.47881(16) 0.83742(7) 0.60842(14) 0.0798(4) Uani 1 1 d . . . . .
N13 N 0.26392(15) 0.65890(8) 0.87434(14) 0.0572(4) Uani 1 1 d . . . . .
O19 O 0.53319(16) 0.72025(8) 1.01881(14) 0.0863(5) Uani 1 1 d . . . . .
C8 C 0.35645(17) 0.70833(8) 0.82856(16) 0.0460(4) Uani 1 1 d . . . . .
C9 C 0.33856(19) 0.74912(10) 0.71521(17) 0.0561(5) Uani 1 1 d . . . . .
H9 H 0.255620 0.746360 0.654589 0.067 Uiso 1 1 calc R U . . .
C12 C 0.49468(18) 0.73452(9) 0.90486(18) 0.0538(4) Uani 1 1 d . . . . .
C10 C 0.4615(2) 0.79610(9) 0.70111(19) 0.0563(5) Uani 1 1 d . . . . .
C11 C 0.57406(19) 0.78726(9) 0.81935(18) 0.0571(5) Uani 1 1 d . . . . .
C1 C 0.70409(18) 0.68239(10) 0.7091(2) 0.0604(5) Uani 1 1 d . . . . .
C18 C 0.3067(2) 0.60440(10) 0.9765(2) 0.0662(5) Uani 1 1 d . . . . .
H18A H 0.235374 0.604747 1.043297 0.079 Uiso 1 1 calc R U . . .
H18B H 0.403755 0.616533 1.019237 0.079 Uiso 1 1 calc R U . . .
C2 C 0.66481(19) 0.68070(10) 0.5744(2) 0.0653(5) Uani 1 1 d . . . . .
H2 H 0.653691 0.724314 0.527140 0.078 Uiso 1 1 calc R U . . .
C7 C 0.72227(19) 0.75413(10) 0.7808(2) 0.0662(5) Uani 1 1 d . . . . .
H7A H 0.769682 0.788786 0.724978 0.079 Uiso 1 1 calc R U . . .
H7B H 0.787850 0.747068 0.860426 0.079 Uiso 1 1 calc R U . . .
C14 C 0.12159(19) 0.64260(12) 0.8012(2) 0.0698(5) Uani 1 1 d . . . . .
H14A H 0.099777 0.679873 0.734152 0.084 Uiso 1 1 calc R U . . .
H14B H 0.043113 0.643557 0.861261 0.084 Uiso 1 1 calc R U . . .
C6 C 0.7225(2) 0.61636(11) 0.7767(2) 0.0742(6) Uani 1 1 d . . . . .
H6 H 0.749611 0.616459 0.867227 0.089 Uiso 1 1 calc R U . . .
C3 C 0.6420(2) 0.61472(11) 0.5099(2) 0.0725(6) Uani 1 1 d . . . . .
C17 C 0.3115(3) 0.52909(11) 0.9149(2) 0.0818(6) Uani 1 1 d . . . . .
H17A H 0.391367 0.527367 0.856241 0.098 Uiso 1 1 calc R U . . .
H17B H 0.332644 0.492935 0.984019 0.098 Uiso 1 1 calc R U . . .
C15 C 0.1250(2) 0.56825(13) 0.7358(2) 0.0813(6) Uani 1 1 d . . . . .
H15A H 0.028028 0.557378 0.691753 0.098 Uiso 1 1 calc R U . . .
H15B H 0.197036 0.568578 0.669663 0.098 Uiso 1 1 calc R U . . .
C4 C 0.6624(2) 0.54905(11) 0.5778(3) 0.0865(7) Uani 1 1 d . . . . .
H4 H 0.649826 0.504553 0.533587 0.104 Uiso 1 1 calc R U . . .
C21 C 0.6049(3) 0.86022(11) 0.8909(2) 0.0880(7) Uani 1 1 d . . . . .
H21A H 0.514213 0.878779 0.921629 0.132 Uiso 1 1 calc R U . . .
H21B H 0.643320 0.894822 0.830894 0.132 Uiso 1 1 calc R U . . .
H21C H 0.676638 0.852813 0.964963 0.132 Uiso 1 1 calc R U . . .
C5 C 0.7011(3) 0.55089(12) 0.7108(3) 0.0884(7) Uani 1 1 d . . . . .
H5 H 0.713093 0.507150 0.757576 0.106 Uiso 1 1 calc R U . . .
C16 C 0.1664(3) 0.51013(13) 0.8377(3) 0.0967(8) Uani 1 1 d . . . . .
H16A H 0.175742 0.463238 0.794012 0.116 Uiso 1 1 calc R U . . .
H16B H 0.088333 0.505910 0.897806 0.116 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
Cl22 C3 1.744(3) . ?
O20 C10 1.224(2) . ?
N13 C8 1.336(2) . ?
N13 C14 1.460(2) . ?
N13 C18 1.465(2) . ?
O19 C12 1.207(2) . ?
C8 C9 1.367(2) . ?
C8 C12 1.491(2) . ?
C9 C10 1.417(3) . ?
C9 H9 0.9300 . ?
C12 C11 1.513(2) . ?
C10 C11 1.515(3) . ?
C11 C21 1.530(3) . ?
C11 C7 1.545(2) . ?
C1 C2 1.382(3) . ?
C1 C6 1.389(3) . ?
C1 C7 1.500(3) . ?
C18 C17 1.511(3) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C2 C3 1.377(3) . ?
C2 H2 0.9300 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C14 C15 1.511(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C6 C5 1.375(3) . ?
C6 H6 0.9300 . ?
C3 C4 1.387(3) . ?
C17 C16 1.510(3) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C15 C16 1.505(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C4 C5 1.365(4) . ?
C4 H4 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C5 H5 0.9300 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?

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
C8 N13 C14 120.58(15) . . ?
C8 N13 C18 124.56(15) . . ?
C14 N13 C18 113.03(15) . . ?
N13 C8 C9 128.62(16) . . ?
N13 C8 C12 123.72(15) . . ?
C9 C8 C12 107.35(15) . . ?
C8 C9 C10 111.93(16) . . ?
C8 C9 H9 124.0 . . ?
C10 C9 H9 124.0 . . ?
O19 C12 C8 126.21(16) . . ?
O19 C12 C11 124.91(16) . . ?
C8 C12 C11 108.72(14) . . ?
O20 C10 C9 126.79(19) . . ?
O20 C10 C11 123.62(17) . . ?
C9 C10 C11 109.59(15) . . ?
C12 C11 C10 101.72(14) . . ?
C12 C11 C21 111.00(16) . . ?
C10 C11 C21 111.51(16) . . ?
C12 C11 C7 110.76(14) . . ?
C10 C11 C7 112.29(15) . . ?
C21 C11 C7 109.40(16) . . ?
C2 C1 C6 118.59(19) . . ?
C2 C1 C7 120.47(17) . . ?
C6 C1 C7 120.9(2) . . ?
N13 C18 C17 109.85(17) . . ?
N13 C18 H18A 109.7 . . ?
C17 C18 H18A 109.7 . . ?
N13 C18 H18B 109.7 . . ?
C17 C18 H18B 109.7 . . ?
H18A C18 H18B 108.2 . . ?
C3 C2 C1 120.31(19) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C1 C7 C11 113.64(14) . . ?
C1 C7 H7A 108.8 . . ?
C11 C7 H7A 108.8 . . ?
C1 C7 H7B 108.8 . . ?
C11 C7 H7B 108.8 . . ?
H7A C7 H7B 107.7 . . ?
N13 C14 C15 110.93(16) . . ?
N13 C14 H14A 109.5 . . ?
C15 C14 H14A 109.5 . . ?
N13 C14 H14B 109.5 . . ?
C15 C14 H14B 109.5 . . ?
H14A C14 H14B 108.0 . . ?
C5 C6 C1 120.5(2) . . ?
C5 C6 H6 119.8 . . ?
C1 C6 H6 119.8 . . ?
C2 C3 C4 120.7(2) . . ?
C2 C3 Cl22 118.86(17) . . ?
C4 C3 Cl22 120.42(19) . . ?
C16 C17 C18 111.71(19) . . ?
C16 C17 H17A 109.3 . . ?
C18 C17 H17A 109.3 . . ?
C16 C17 H17B 109.3 . . ?
C18 C17 H17B 109.3 . . ?
H17A C17 H17B 107.9 . . ?
C16 C15 C14 110.17(19) . . ?
C16 C15 H15A 109.6 . . ?
C14 C15 H15A 109.6 . . ?
C16 C15 H15B 109.6 . . ?
C14 C15 H15B 109.6 . . ?
H15A C15 H15B 108.1 . . ?
C5 C4 C3 118.8(2) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C11 C21 H21A 109.5 . . ?
C11 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C11 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C4 C5 C6 121.0(2) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C15 C16 C17 110.49(18) . . ?
C15 C16 H16A 109.6 . . ?
C17 C16 H16A 109.6 . . ?
C15 C16 H16B 109.6 . . ?
C17 C16 H16B 109.6 . . ?
H16A C16 H16B 108.1 . . ?

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
C14 N13 C8 C9 -0.3(3) . . . . ?
C18 N13 C8 C9 163.18(17) . . . . ?
C14 N13 C8 C12 172.37(15) . . . . ?
C18 N13 C8 C12 -24.1(2) . . . . ?
N13 C8 C9 C10 179.67(15) . . . . ?
C12 C8 C9 C10 6.03(19) . . . . ?
N13 C8 C12 O19 -7.1(3) . . . . ?
C9 C8 C12 O19 166.96(18) . . . . ?
N13 C8 C12 C11 177.38(14) . . . . ?
C9 C8 C12 C11 -8.59(18) . . . . ?
C8 C9 C10 O20 177.91(16) . . . . ?
C8 C9 C10 C11 -1.2(2) . . . . ?
O19 C12 C11 C10 -168.18(18) . . . . ?
C8 C12 C11 C10 7.44(17) . . . . ?
O19 C12 C11 C21 -49.4(2) . . . . ?
C8 C12 C11 C21 126.17(17) . . . . ?
O19 C12 C11 C7 72.3(2) . . . . ?
C8 C12 C11 C7 -112.09(16) . . . . ?
O20 C10 C11 C12 176.86(16) . . . . ?
C9 C10 C11 C12 -4.00(17) . . . . ?
O20 C10 C11 C21 58.5(2) . . . . ?
C9 C10 C11 C21 -122.37(17) . . . . ?
O20 C10 C11 C7 -64.7(2) . . . . ?
C9 C10 C11 C7 114.44(15) . . . . ?
C8 N13 C18 C17 -107.87(19) . . . . ?
C14 N13 C18 C17 56.7(2) . . . . ?
C6 C1 C2 C3 1.1(3) . . . . ?
C7 C1 C2 C3 -177.24(15) . . . . ?
C2 C1 C7 C11 82.5(2) . . . . ?
C6 C1 C7 C11 -95.8(2) . . . . ?
C12 C11 C7 C1 57.7(2) . . . . ?
C10 C11 C7 C1 -55.3(2) . . . . ?
C21 C11 C7 C1 -179.67(17) . . . . ?
C8 N13 C14 C15 107.11(19) . . . . ?
C18 N13 C14 C15 -58.2(2) . . . . ?
C2 C1 C6 C5 -0.4(3) . . . . ?
C7 C1 C6 C5 177.95(17) . . . . ?
C1 C2 C3 C4 -1.9(3) . . . . ?
C1 C2 C3 Cl22 177.44(13) . . . . ?
N13 C18 C17 C16 -54.8(2) . . . . ?
N13 C14 C15 C16 56.3(2) . . . . ?
C2 C3 C4 C5 1.9(3) . . . . ?
Cl22 C3 C4 C5 -177.42(17) . . . . ?
C3 C4 C5 C6 -1.2(3) . . . . ?
C1 C6 C5 C4 0.5(3) . . . . ?
C14 C15 C16 C17 -54.9(2) . . . . ?
C18 C17 C16 C15 54.9(2) . . . . ?

_refine_diff_density_max         0.332
_refine_diff_density_min         -0.396
_refine_diff_density_rms         0.032

