# Supplementary Information (SI) for RSC Advances.
# 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_ab1332
_database_code_depnum_ccdc_archive 'CCDC 2360616'
loop_
_audit_author_name
_audit_author_address
'Matti Haukka'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2024-06-05 deposited with the CCDC.	2024-12-16 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         'C11 H8 Cl3 N3 O'
_chemical_formula_sum            'C11 H8 Cl3 N3 O'
_chemical_formula_weight         304.55

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
Cl Cl 0.3639 0.7018 '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'

_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                   10.62874(18)
_cell_length_b                   10.43514(18)
_cell_length_c                   11.62031(19)
_cell_angle_alpha                90
_cell_angle_beta                 93.7149(15)
_cell_angle_gamma                90
_cell_volume                     1286.13(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    121(2)
_cell_measurement_reflns_used    8704
_cell_measurement_theta_min      5.4550
_cell_measurement_theta_max      78.8710

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.573
_exptl_crystal_F_000             616
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.155
_exptl_crystal_size_mid          0.105
_exptl_crystal_size_min          0.032
_exptl_absorpt_coefficient_mu    6.387
_shelx_estimated_absorpt_T_min   0.438
_shelx_estimated_absorpt_T_max   0.822
_exptl_absorpt_correction_T_min  0.47576
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.80a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      121(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_probe          x-ray
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dualflex, HyPix-Arc 100'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            'HyPix-Arc 100'
_diffrn_reflns_number            16383
_diffrn_reflns_av_unetI/netI     0.0218
_diffrn_reflns_av_R_equivalents  0.0343
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         5.467
_diffrn_reflns_theta_max         79.465
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2740
_reflns_number_gt                2460
_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       
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
;
_computing_cell_refinement       
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
;
_computing_data_reduction        
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
;
_computing_structure_solution    'SHELXT (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/3 (Sheldrick, 2019)'
_computing_molecular_graphics    
'CrystaMaker X (CrystalMaker Software ltd., 2022)'
_computing_publication_material  'SHELXL-2019/3 (Sheldrick, 2019)'
_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)+(0.0478P)²+0.5019P] 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         2740
_refine_ls_number_parameters     165
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0345
_refine_ls_R_factor_gt           0.0309
_refine_ls_wR_factor_ref         0.0861
_refine_ls_wR_factor_gt          0.0839
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.072
_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
Cl1 Cl 0.88968(4) 0.34659(5) 0.87932(3) 0.03676(13) Uani 1 1 d . . . . .
Cl2 Cl 1.13491(4) 0.29718(4) 0.49224(4) 0.03398(12) Uani 1 1 d . . . . .
Cl3 Cl 0.64692(4) 0.43168(5) 0.46302(4) 0.03987(13) Uani 1 1 d . . . . .
O1 O 0.29578(11) 0.28847(12) 0.76958(11) 0.0336(3) Uani 1 1 d . . . . .
N1 N 0.66565(13) 0.41172(13) 0.71996(12) 0.0280(3) Uani 1 1 d . . . . .
N2 N 0.65038(14) 0.52729(14) 0.77491(14) 0.0351(3) Uani 1 1 d . . . . .
N3 N 0.53715(14) 0.52685(14) 0.81044(14) 0.0340(3) Uani 1 1 d . . . . .
C1 C 0.88998(16) 0.35423(15) 0.73093(14) 0.0279(3) Uani 1 1 d . . . . .
C2 C 1.00064(15) 0.32773(15) 0.67887(14) 0.0280(3) Uani 1 1 d . . . . .
H2 H 1.075735 0.306592 0.723628 0.034 Uiso 1 1 calc R U . . .
C3 C 0.99867(16) 0.33293(15) 0.56005(15) 0.0283(3) Uani 1 1 d . . . . .
C4 C 0.89091(16) 0.36462(16) 0.49196(15) 0.0301(3) Uani 1 1 d . . . . .
H4 H 0.892120 0.368264 0.410355 0.036 Uiso 1 1 calc R U . . .
C5 C 0.78170(16) 0.39075(16) 0.54639(14) 0.0294(3) Uani 1 1 d . . . . .
C6 C 0.77896(15) 0.38527(15) 0.66616(14) 0.0280(3) Uani 1 1 d . . . . .
C7 C 0.56034(15) 0.33909(15) 0.72076(14) 0.0261(3) Uani 1 1 d . . . . .
C8 C 0.55104(17) 0.20805(17) 0.67020(15) 0.0325(4) Uani 1 1 d . . . . .
H8A H 0.534726 0.214353 0.586411 0.049 Uiso 1 1 calc R U . . .
H8B H 0.481879 0.161464 0.703212 0.049 Uiso 1 1 calc R U . . .
H8C H 0.630388 0.162087 0.687682 0.049 Uiso 1 1 calc R U . . .
C9 C 0.47819(15) 0.41397(15) 0.77916(14) 0.0276(3) Uani 1 1 d . . . . .
C10 C 0.34734(16) 0.38676(17) 0.80479(14) 0.0301(3) Uani 1 1 d . . . . .
C11 C 0.28182(18) 0.4832(2) 0.87536(19) 0.0427(5) Uani 1 1 d . . . . .
H11A H 0.275203 0.564725 0.833614 0.064 Uiso 1 1 calc R U . . .
H11B H 0.330191 0.495769 0.949179 0.064 Uiso 1 1 calc R U . . .
H11C H 0.197195 0.452033 0.889453 0.064 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
Cl1 C1 1.7265(17) . yes
Cl2 C3 1.7335(17) . yes
Cl3 C5 1.7302(17) . yes
O1 C10 1.221(2) . yes
N1 C7 1.352(2) . yes
N1 N2 1.379(2) . yes
N1 C6 1.419(2) . yes
N2 N3 1.297(2) . yes
N3 C9 1.372(2) . yes
C1 C2 1.385(2) . ?
C1 C6 1.396(2) . ?
C2 C3 1.381(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.389(2) . ?
C4 C5 1.385(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.395(2) . ?
C7 C9 1.382(2) . ?
C7 C8 1.489(2) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.469(2) . ?
C10 C11 1.498(2) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?

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 111.38(13) . . ?
C7 N1 C6 128.34(14) . . ?
N2 N1 C6 120.18(14) . . ?
N3 N2 N1 106.48(13) . . ?
N2 N3 C9 109.62(14) . . ?
C2 C1 C6 121.53(15) . . ?
C2 C1 Cl1 118.93(13) . . ?
C6 C1 Cl1 119.54(13) . . ?
C3 C2 C1 118.08(15) . . ?
C3 C2 H2 121.0 . . ?
C1 C2 H2 121.0 . . ?
C2 C3 C4 122.51(16) . . ?
C2 C3 Cl2 119.16(13) . . ?
C4 C3 Cl2 118.33(13) . . ?
C5 C4 C3 118.12(16) . . ?
C5 C4 H4 120.9 . . ?
C3 C4 H4 120.9 . . ?
C4 C5 C6 121.33(15) . . ?
C4 C5 Cl3 118.75(13) . . ?
C6 C5 Cl3 119.91(13) . . ?
C5 C6 C1 118.41(15) . . ?
C5 C6 N1 120.30(15) . . ?
C1 C6 N1 121.29(15) . . ?
N1 C7 C9 103.65(14) . . ?
N1 C7 C8 123.08(15) . . ?
C9 C7 C8 133.24(15) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N3 C9 C7 108.86(14) . . ?
N3 C9 C10 122.30(15) . . ?
C7 C9 C10 128.82(15) . . ?
O1 C10 C9 120.32(15) . . ?
O1 C10 C11 122.21(16) . . ?
C9 C10 C11 117.46(16) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 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
C7 N1 N2 N3 0.40(19) . . . . ?
C6 N1 N2 N3 176.98(15) . . . . ?
N1 N2 N3 C9 -0.40(19) . . . . ?
C6 C1 C2 C3 0.1(2) . . . . ?
Cl1 C1 C2 C3 179.29(12) . . . . ?
C1 C2 C3 C4 0.6(2) . . . . ?
C1 C2 C3 Cl2 -178.75(12) . . . . ?
C2 C3 C4 C5 -0.5(3) . . . . ?
Cl2 C3 C4 C5 178.81(13) . . . . ?
C3 C4 C5 C6 -0.2(3) . . . . ?
C3 C4 C5 Cl3 179.48(13) . . . . ?
C4 C5 C6 C1 0.8(2) . . . . ?
Cl3 C5 C6 C1 -178.84(12) . . . . ?
C4 C5 C6 N1 -179.63(15) . . . . ?
Cl3 C5 C6 N1 0.7(2) . . . . ?
C2 C1 C6 C5 -0.8(2) . . . . ?
Cl1 C1 C6 C5 -179.97(13) . . . . ?
C2 C1 C6 N1 179.69(15) . . . . ?
Cl1 C1 C6 N1 0.5(2) . . . . ?
C7 N1 C6 C5 71.7(2) . . . . ?
N2 N1 C6 C5 -104.20(19) . . . . ?
C7 N1 C6 C1 -108.7(2) . . . . ?
N2 N1 C6 C1 75.3(2) . . . . ?
N2 N1 C7 C9 -0.23(18) . . . . ?
C6 N1 C7 C9 -176.47(15) . . . . ?
N2 N1 C7 C8 -178.39(15) . . . . ?
C6 N1 C7 C8 5.4(3) . . . . ?
N2 N3 C9 C7 0.3(2) . . . . ?
N2 N3 C9 C10 -178.36(15) . . . . ?
N1 C7 C9 N3 -0.01(18) . . . . ?
C8 C7 C9 N3 177.87(17) . . . . ?
N1 C7 C9 C10 178.50(16) . . . . ?
C8 C7 C9 C10 -3.6(3) . . . . ?
N3 C9 C10 O1 175.66(16) . . . . ?
C7 C9 C10 O1 -2.7(3) . . . . ?
N3 C9 C10 C11 -4.7(2) . . . . ?
C7 C9 C10 C11 176.99(17) . . . . ?

_refine_diff_density_max         0.341
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.053

####################################################################### 
# 
# 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_ab1417_pr
_database_code_depnum_ccdc_archive 'CCDC 2360617'
loop_
_audit_author_name
_audit_author_address
'Matti Haukka'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2024-06-05 deposited with the CCDC.	2024-12-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/2
_shelx_SHELXL_version_number     2019/2
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H12 Cl3 N3 O2'
_chemical_formula_sum            'C20 H12 Cl3 N3 O2'
_chemical_formula_weight         432.68

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           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   7.66680(10)
_cell_length_b                   13.8977(2)
_cell_length_c                   9.5441(2)
_cell_angle_alpha                90
_cell_angle_beta                 111.742(2)
_cell_angle_gamma                90
_cell_volume                     944.59(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    8893
_cell_measurement_theta_min      2.7100
_cell_measurement_theta_max      36.2310

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.521
_exptl_crystal_F_000             440
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.507
_shelx_estimated_absorpt_T_min   0.888
_shelx_estimated_absorpt_T_max   0.961
_exptl_absorpt_correction_T_min  0.88196
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'φ scans and ω scans with κ offset'
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_detector_area_resol_mean 16.0107
_diffrn_reflns_number            19035
_diffrn_reflns_av_unetI/netI     0.0451
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.297
_diffrn_reflns_theta_max         37.323
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             9361
_reflns_number_gt                8190
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.915
_reflns_Friedel_fraction_max     0.941
_reflns_Friedel_fraction_full    1.000

_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       
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
;
_computing_cell_refinement       
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
;
_computing_data_reduction        
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
;
_computing_structure_solution    'SHELXT (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    
'CrystaMaker X (CrystalMaker Software ltd., 2022)'
_computing_publication_material  'SHELXL-2019/2 (Sheldrick, 2019)'
_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)+(0.0350P)²+0.0239P] 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_abs_structure_details 
;
 Flack x determined using 3365 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.019(18)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         9361
_refine_ls_number_parameters     254
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0463
_refine_ls_R_factor_gt           0.0373
_refine_ls_wR_factor_ref         0.0819
_refine_ls_wR_factor_gt          0.0772
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_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
Cl1 Cl 1.29386(7) 0.56510(3) 0.90112(5) 0.02253(9) Uani 1 1 d . . . . .
Cl2 Cl 1.69847(7) 0.27559(3) 1.24445(5) 0.02450(10) Uani 1 1 d . . . . .
Cl3 Cl 0.94833(7) 0.24328(3) 0.98048(6) 0.02562(10) Uani 1 1 d . . . . .
O1 O 0.5746(2) 0.46505(11) 0.41345(15) 0.0244(3) Uani 1 1 d . . . . .
O2 O 0.04151(19) 0.62523(10) 0.51802(14) 0.0191(2) Uani 1 1 d . . . . .
N1 N 0.9647(2) 0.44037(11) 0.85939(16) 0.0171(3) Uani 1 1 d . . . . .
N2 N 0.8571(2) 0.49074(12) 0.92125(17) 0.0226(3) Uani 1 1 d . . . . .
N3 N 0.7044(2) 0.51570(12) 0.80962(18) 0.0219(3) Uani 1 1 d . . . . .
C1 C 1.3068(3) 0.45232(12) 0.98037(19) 0.0173(3) Uani 1 1 d . . . . .
C2 C 1.4808(3) 0.41489(13) 1.0691(2) 0.0186(3) Uani 1 1 d . . . . .
H2 H 1.592980 0.450484 1.087874 0.022 Uiso 1 1 calc R U . . .
C3 C 1.4849(3) 0.32322(13) 1.12958(19) 0.0179(3) Uani 1 1 d . . . . .
C4 C 1.3236(3) 0.26848(13) 1.10260(19) 0.0190(3) Uani 1 1 d . . . . .
H4 H 1.330814 0.205592 1.143358 0.023 Uiso 1 1 calc R U . . .
C5 C 1.1519(3) 0.30849(13) 1.0143(2) 0.0180(3) Uani 1 1 d . . . . .
C6 C 1.1410(3) 0.40074(12) 0.95223(18) 0.0163(3) Uani 1 1 d . . . . .
C7 C 0.8803(3) 0.43432(12) 0.70707(18) 0.0160(3) Uani 1 1 d . . . . .
C8 C 0.9645(3) 0.38275(15) 0.6110(2) 0.0246(4) Uani 1 1 d . . . . .
H8A H 1.101549 0.388535 0.655630 0.037 Uiso 1 1 calc R U . . .
H8B H 0.918245 0.411053 0.509797 0.037 Uiso 1 1 calc R U . . .
H8C H 0.929198 0.314641 0.604377 0.037 Uiso 1 1 calc R U . . .
C9 C 0.7126(2) 0.48279(12) 0.67646(19) 0.0165(3) Uani 1 1 d . . . . .
C10 C 0.5566(3) 0.49433(13) 0.5289(2) 0.0181(3) Uani 1 1 d . . . . .
C11 C 0.3814(3) 0.53881(13) 0.5286(2) 0.0195(3) Uani 1 1 d . . . . .
H11 H 0.376084 0.563482 0.619752 0.023 Uiso 1 1 calc R U . . .
C12 C 0.2291(3) 0.54460(13) 0.3999(2) 0.0204(3) Uani 1 1 d . . . . .
H12 H 0.238340 0.517660 0.311427 0.025 Uiso 1 1 calc R U . . .
C13 C 0.0543(3) 0.58832(13) 0.3864(2) 0.0190(3) Uani 1 1 d . . . . .
C14 C -0.1063(3) 0.60468(14) 0.2647(2) 0.0201(3) Uani 1 1 d . . . . .
H14 H -0.131610 0.585177 0.163621 0.024 Uiso 1 1 calc R U . . .
C15 C -0.2302(3) 0.65724(13) 0.3191(2) 0.0181(3) Uani 1 1 d . . . . .
C16 C -0.4096(3) 0.69859(15) 0.2539(2) 0.0235(4) Uani 1 1 d . . . . .
H16 H -0.480128 0.692796 0.148866 0.028 Uiso 1 1 calc R U . . .
C17 C -0.4807(3) 0.74805(16) 0.3471(2) 0.0264(4) Uani 1 1 d . . . . .
H17 H -0.601152 0.777037 0.304615 0.032 Uiso 1 1 calc R U . . .
C18 C -0.3786(3) 0.75638(14) 0.5032(2) 0.0247(4) Uani 1 1 d . . . . .
H18 H -0.432035 0.790363 0.563892 0.030 Uiso 1 1 calc R U . . .
C19 C -0.2015(3) 0.71597(13) 0.5702(2) 0.0213(3) Uani 1 1 d . . . . .
H19 H -0.131622 0.721160 0.675472 0.026 Uiso 1 1 calc R U . . .
C20 C -0.1323(3) 0.66757(12) 0.47472(19) 0.0170(3) Uani 1 1 d . . . . .


_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
Cl1 C1 1.7271(17) . yes
Cl2 C3 1.7297(18) . yes
Cl3 C5 1.7284(19) . yes
O1 C10 1.229(2) . yes
O2 C20 1.373(2) . yes
O2 C13 1.394(2) . yes
N1 C7 1.357(2) . yes
N1 N2 1.372(2) . yes
N1 C6 1.424(2) . yes
N2 N3 1.305(2) . yes
N3 C9 1.374(2) . yes
C1 C2 1.390(3) . ?
C1 C6 1.396(3) . ?
C2 C3 1.394(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.392(3) . ?
C4 C5 1.390(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.402(2) . ?
C7 C9 1.383(2) . ?
C7 C8 1.486(2) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.480(2) . ?
C10 C11 1.478(3) . ?
C11 C12 1.348(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.433(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.363(3) . ?
C14 C15 1.439(3) . ?
C14 H14 0.9500 . ?
C15 C20 1.402(2) . ?
C15 C16 1.405(3) . ?
C16 C17 1.385(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.408(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.387(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.387(3) . ?
C19 H19 0.9500 . ?

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
C20 O2 C13 105.73(13) . . ?
C7 N1 N2 111.62(15) . . ?
C7 N1 C6 127.49(15) . . ?
N2 N1 C6 120.89(14) . . ?
N3 N2 N1 106.58(14) . . ?
N2 N3 C9 109.38(15) . . ?
C2 C1 C6 121.68(16) . . ?
C2 C1 Cl1 119.54(14) . . ?
C6 C1 Cl1 118.78(13) . . ?
C1 C2 C3 117.63(17) . . ?
C1 C2 H2 121.2 . . ?
C3 C2 H2 121.2 . . ?
C4 C3 C2 122.73(17) . . ?
C4 C3 Cl2 118.40(13) . . ?
C2 C3 Cl2 118.87(15) . . ?
C5 C4 C3 118.08(16) . . ?
C5 C4 H4 121.0 . . ?
C3 C4 H4 121.0 . . ?
C4 C5 C6 121.11(17) . . ?
C4 C5 Cl3 119.38(14) . . ?
C6 C5 Cl3 119.51(14) . . ?
C1 C6 C5 118.76(16) . . ?
C1 C6 N1 120.51(15) . . ?
C5 C6 N1 120.71(17) . . ?
N1 C7 C9 103.48(14) . . ?
N1 C7 C8 123.14(16) . . ?
C9 C7 C8 133.36(16) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N3 C9 C7 108.93(15) . . ?
N3 C9 C10 123.09(16) . . ?
C7 C9 C10 127.87(15) . . ?
O1 C10 C11 122.69(16) . . ?
O1 C10 C9 119.84(16) . . ?
C11 C10 C9 117.44(15) . . ?
C12 C11 C10 120.46(16) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C11 C12 C13 124.96(17) . . ?
C11 C12 H12 117.5 . . ?
C13 C12 H12 117.5 . . ?
C14 C13 O2 111.32(16) . . ?
C14 C13 C12 131.85(16) . . ?
O2 C13 C12 116.78(16) . . ?
C13 C14 C15 106.61(15) . . ?
C13 C14 H14 126.7 . . ?
C15 C14 H14 126.7 . . ?
C20 C15 C16 118.65(17) . . ?
C20 C15 C14 105.57(16) . . ?
C16 C15 C14 135.75(17) . . ?
C17 C16 C15 118.16(18) . . ?
C17 C16 H16 120.9 . . ?
C15 C16 H16 120.9 . . ?
C16 C17 C18 121.56(18) . . ?
C16 C17 H17 119.2 . . ?
C18 C17 H17 119.2 . . ?
C19 C18 C17 121.34(18) . . ?
C19 C18 H18 119.3 . . ?
C17 C18 H18 119.3 . . ?
C20 C19 C18 116.15(17) . . ?
C20 C19 H19 121.9 . . ?
C18 C19 H19 121.9 . . ?
O2 C20 C19 125.10(16) . . ?
O2 C20 C15 110.75(15) . . ?
C19 C20 C15 124.13(17) . . ?

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
C7 N1 N2 N3 0.7(2) . . . . ?
C6 N1 N2 N3 -178.66(16) . . . . ?
N1 N2 N3 C9 -0.5(2) . . . . ?
C6 C1 C2 C3 0.1(3) . . . . ?
Cl1 C1 C2 C3 -179.36(13) . . . . ?
C1 C2 C3 C4 1.0(3) . . . . ?
C1 C2 C3 Cl2 -178.39(14) . . . . ?
C2 C3 C4 C5 -1.5(3) . . . . ?
Cl2 C3 C4 C5 177.89(13) . . . . ?
C3 C4 C5 C6 0.9(3) . . . . ?
C3 C4 C5 Cl3 -179.14(13) . . . . ?
C2 C1 C6 C5 -0.6(3) . . . . ?
Cl1 C1 C6 C5 178.85(13) . . . . ?
C2 C1 C6 N1 -179.24(16) . . . . ?
Cl1 C1 C6 N1 0.2(2) . . . . ?
C4 C5 C6 C1 0.1(3) . . . . ?
Cl3 C5 C6 C1 -179.85(13) . . . . ?
C4 C5 C6 N1 178.72(16) . . . . ?
Cl3 C5 C6 N1 -1.2(2) . . . . ?
C7 N1 C6 C1 87.3(2) . . . . ?
N2 N1 C6 C1 -93.5(2) . . . . ?
C7 N1 C6 C5 -91.3(2) . . . . ?
N2 N1 C6 C5 87.9(2) . . . . ?
N2 N1 C7 C9 -0.60(19) . . . . ?
C6 N1 C7 C9 178.70(17) . . . . ?
N2 N1 C7 C8 -179.25(17) . . . . ?
C6 N1 C7 C8 0.0(3) . . . . ?
N2 N3 C9 C7 0.1(2) . . . . ?
N2 N3 C9 C10 176.50(17) . . . . ?
N1 C7 C9 N3 0.30(19) . . . . ?
C8 C7 C9 N3 178.7(2) . . . . ?
N1 C7 C9 C10 -175.88(17) . . . . ?
C8 C7 C9 C10 2.6(3) . . . . ?
N3 C9 C10 O1 178.44(18) . . . . ?
C7 C9 C10 O1 -5.9(3) . . . . ?
N3 C9 C10 C11 -3.4(3) . . . . ?
C7 C9 C10 C11 172.28(17) . . . . ?
O1 C10 C11 C12 3.3(3) . . . . ?
C9 C10 C11 C12 -174.80(17) . . . . ?
C10 C11 C12 C13 -178.35(18) . . . . ?
C20 O2 C13 C14 -1.3(2) . . . . ?
C20 O2 C13 C12 176.56(15) . . . . ?
C11 C12 C13 C14 175.6(2) . . . . ?
C11 C12 C13 O2 -1.6(3) . . . . ?
O2 C13 C14 C15 1.3(2) . . . . ?
C12 C13 C14 C15 -176.07(19) . . . . ?
C13 C14 C15 C20 -0.8(2) . . . . ?
C13 C14 C15 C16 177.2(2) . . . . ?
C20 C15 C16 C17 0.2(3) . . . . ?
C14 C15 C16 C17 -177.6(2) . . . . ?
C15 C16 C17 C18 -0.7(3) . . . . ?
C16 C17 C18 C19 0.5(3) . . . . ?
C17 C18 C19 C20 0.1(3) . . . . ?
C13 O2 C20 C19 -178.00(17) . . . . ?
C13 O2 C20 C15 0.68(19) . . . . ?
C18 C19 C20 O2 177.99(17) . . . . ?
C18 C19 C20 C15 -0.5(3) . . . . ?
C16 C15 C20 O2 -178.33(17) . . . . ?
C14 C15 C20 O2 0.1(2) . . . . ?
C16 C15 C20 C19 0.4(3) . . . . ?
C14 C15 C20 C19 178.78(18) . . . . ?

_refine_diff_density_max         0.341
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.058

####################################################################### 
# 
# 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_ab1424
_database_code_depnum_ccdc_archive 'CCDC 2360618'
loop_
_audit_author_name
_audit_author_address
'Matti Haukka'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2024-06-05 deposited with the CCDC.	2024-12-16 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         'C20 H12 Cl3 N3 O S'
_chemical_formula_sum            'C20 H12 Cl3 N3 O S'
_chemical_formula_weight         448.74

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'
Cl Cl 0.3639 0.7018 '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           15
_space_group_name_H-M_alt        'I 2/a'
_space_group_name_Hall           '-I 2ya'

_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, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   25.8395(3)
_cell_length_b                   7.12869(6)
_cell_length_c                   23.3863(2)
_cell_angle_alpha                90
_cell_angle_beta                 114.7797(13)
_cell_angle_gamma                90
_cell_volume                     3911.17(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    34616
_cell_measurement_theta_min      4.1540
_cell_measurement_theta_max      78.3450

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.524
_exptl_crystal_F_000             1824
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.124
_exptl_crystal_size_mid          0.105
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    5.383
_shelx_estimated_absorpt_T_min   0.555
_shelx_estimated_absorpt_T_max   0.738
_exptl_absorpt_correction_T_min  0.958
_exptl_absorpt_correction_T_max  0.976
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_probe          x-ray
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dualflex, HyPix-Arc 100'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            'HyPix-Arc 100'
_diffrn_reflns_number            63498
_diffrn_reflns_av_unetI/netI     0.0126
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         3.768
_diffrn_reflns_theta_max         79.177
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4221
_reflns_number_gt                3965
_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       
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
;
_computing_cell_refinement       
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
;
_computing_data_reduction        
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
;
_computing_structure_solution    'SHELXT (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/3 (Sheldrick, 2019)'
_computing_molecular_graphics    
'CrystaMaker X (CrystalMaker Software ltd., 2022)'
_computing_publication_material  'SHELXL-2019/3 (Sheldrick, 2019)'
_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)+(0.0390P)²+3.2884P] 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         4221
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0304
_refine_ls_R_factor_gt           0.0289
_refine_ls_wR_factor_ref         0.0799
_refine_ls_wR_factor_gt          0.0790
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_restrained_S_all      1.098
_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
Cl1 Cl 0.54281(2) 1.09610(6) 0.26509(2) 0.04304(11) Uani 1 1 d . . . . .
Cl2 Cl 0.65438(2) 1.70362(6) 0.39349(2) 0.04510(11) Uani 1 1 d . . . . .
Cl3 Cl 0.52482(2) 1.30035(6) 0.47746(2) 0.04078(11) Uani 1 1 d . . . . .
S1 S 0.35904(2) 0.26558(6) 0.41812(2) 0.03452(10) Uani 1 1 d . . . . .
O1 O 0.33069(5) 0.88238(16) 0.27245(5) 0.0383(3) Uani 1 1 d . . . . .
N1 N 0.50079(5) 1.06089(17) 0.36554(5) 0.0276(2) Uani 1 1 d . . . . .
N2 N 0.51957(5) 0.89530(18) 0.39811(6) 0.0321(3) Uani 1 1 d . . . . .
N3 N 0.47467(5) 0.79110(18) 0.38421(6) 0.0315(3) Uani 1 1 d . . . . .
C1 C 0.56113(6) 1.2442(2) 0.32896(7) 0.0299(3) Uani 1 1 d . . . . .
C2 C 0.59719(6) 1.3941(2) 0.33475(7) 0.0307(3) Uani 1 1 d . . . . .
H2 H 0.613011 1.413170 0.305137 0.037 Uiso 1 1 calc R U . . .
C3 C 0.60939(6) 1.5149(2) 0.38507(7) 0.0323(3) Uani 1 1 d . . . . .
C4 C 0.58737(6) 1.4900(2) 0.42902(7) 0.0336(3) Uani 1 1 d . . . . .
H4 H 0.596101 1.575815 0.462883 0.040 Uiso 1 1 calc R U . . .
C5 C 0.55227(6) 1.3374(2) 0.42276(7) 0.0303(3) Uani 1 1 d . . . . .
C6 C 0.53875(6) 1.2126(2) 0.37277(7) 0.0276(3) Uani 1 1 d . . . . .
C7 C 0.44380(6) 1.0601(2) 0.33143(6) 0.0274(3) Uani 1 1 d . . . . .
C8 C 0.41224(7) 1.2229(2) 0.29343(7) 0.0336(3) Uani 1 1 d . . . . .
H8A H 0.426980 1.338697 0.317310 0.050 Uiso 1 1 calc R U . . .
H8B H 0.371638 1.210106 0.283678 0.050 Uiso 1 1 calc R U . . .
H8C H 0.417216 1.227528 0.254150 0.050 Uiso 1 1 calc R U . . .
C9 C 0.42719(6) 0.8859(2) 0.34326(6) 0.0277(3) Uani 1 1 d . . . . .
C10 C 0.36940(6) 0.8051(2) 0.31704(7) 0.0300(3) Uani 1 1 d . . . . .
C11 C 0.36213(6) 0.6312(2) 0.34643(7) 0.0311(3) Uani 1 1 d . . . . .
H11 H 0.393529 0.583821 0.382166 0.037 Uiso 1 1 calc R U . . .
C12 C 0.31261(6) 0.5365(2) 0.32456(7) 0.0316(3) Uani 1 1 d . . . . .
H12 H 0.281167 0.587322 0.289611 0.038 Uiso 1 1 calc R U . . .
C13 C 0.30439(6) 0.3623(2) 0.35103(7) 0.0301(3) Uani 1 1 d . . . . .
C14 C 0.25711(6) 0.2508(2) 0.32864(7) 0.0320(3) Uani 1 1 d . . . . .
H14 H 0.223399 0.281251 0.292524 0.038 Uiso 1 1 calc R U . . .
C15 C 0.26317(6) 0.0832(2) 0.36486(7) 0.0308(3) Uani 1 1 d . . . . .
C16 C 0.22483(7) -0.0651(2) 0.35583(8) 0.0391(4) Uani 1 1 d . . . . .
H16 H 0.188624 -0.064367 0.320862 0.047 Uiso 1 1 calc R U . . .
C17 C 0.24006(8) -0.2119(2) 0.39803(9) 0.0431(4) Uani 1 1 d . . . . .
H17 H 0.214272 -0.313060 0.391569 0.052 Uiso 1 1 calc R U . . .
C18 C 0.29283(8) -0.2144(2) 0.45020(9) 0.0423(4) Uani 1 1 d . . . . .
H18 H 0.301967 -0.315631 0.479225 0.051 Uiso 1 1 calc R U . . .
C19 C 0.33179(7) -0.0723(2) 0.46014(8) 0.0387(3) Uani 1 1 d . . . . .
H19 H 0.367747 -0.074232 0.495470 0.046 Uiso 1 1 calc R U . . .
C20 C 0.31685(6) 0.0746(2) 0.41675(7) 0.0312(3) Uani 1 1 d . . . . .


_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
Cl1 C1 1.7256(15) . yes
Cl2 C3 1.7345(16) . yes
Cl3 C5 1.7235(15) . yes
S1 C20 1.7360(16) . yes
S1 C13 1.7533(15) . yes
O1 C10 1.2317(18) . yes
N1 C7 1.3493(18) . yes
N1 N2 1.3781(17) . yes
N1 C6 1.4215(18) . yes
N2 N3 1.2989(18) . yes
N3 C9 1.3763(18) . yes
C1 C2 1.386(2) . ?
C1 C6 1.390(2) . ?
C2 C3 1.384(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.379(2) . ?
C4 C5 1.384(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.392(2) . ?
C7 C9 1.379(2) . ?
C7 C8 1.481(2) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.473(2) . ?
C10 C11 1.467(2) . ?
C11 C12 1.344(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.443(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.365(2) . ?
C14 C15 1.434(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.403(2) . ?
C15 C20 1.411(2) . ?
C16 C17 1.378(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.398(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.378(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.395(2) . ?
C19 H19 0.9500 . ?

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
C20 S1 C13 91.60(7) . . ?
C7 N1 N2 111.56(12) . . ?
C7 N1 C6 126.95(12) . . ?
N2 N1 C6 121.35(11) . . ?
N3 N2 N1 106.31(11) . . ?
N2 N3 C9 109.61(12) . . ?
C2 C1 C6 121.57(13) . . ?
C2 C1 Cl1 119.03(11) . . ?
C6 C1 Cl1 119.38(11) . . ?
C3 C2 C1 117.82(14) . . ?
C3 C2 H2 121.1 . . ?
C1 C2 H2 121.1 . . ?
C4 C3 C2 122.39(14) . . ?
C4 C3 Cl2 118.77(12) . . ?
C2 C3 Cl2 118.84(12) . . ?
C3 C4 C5 118.61(14) . . ?
C3 C4 H4 120.7 . . ?
C5 C4 H4 120.7 . . ?
C4 C5 C6 120.92(13) . . ?
C4 C5 Cl3 119.80(11) . . ?
C6 C5 Cl3 119.28(12) . . ?
C1 C6 C5 118.66(13) . . ?
C1 C6 N1 121.03(13) . . ?
C5 C6 N1 120.25(13) . . ?
N1 C7 C9 103.85(12) . . ?
N1 C7 C8 122.79(13) . . ?
C9 C7 C8 133.34(13) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N3 C9 C7 108.66(12) . . ?
N3 C9 C10 123.37(13) . . ?
C7 C9 C10 127.95(13) . . ?
O1 C10 C11 123.82(14) . . ?
O1 C10 C9 119.95(14) . . ?
C11 C10 C9 116.23(13) . . ?
C12 C11 C10 122.31(14) . . ?
C12 C11 H11 118.8 . . ?
C10 C11 H11 118.8 . . ?
C11 C12 C13 123.85(14) . . ?
C11 C12 H12 118.1 . . ?
C13 C12 H12 118.1 . . ?
C14 C13 C12 127.30(14) . . ?
C14 C13 S1 111.72(12) . . ?
C12 C13 S1 120.95(11) . . ?
C13 C14 C15 113.57(13) . . ?
C13 C14 H14 123.2 . . ?
C15 C14 H14 123.2 . . ?
C16 C15 C20 118.31(14) . . ?
C16 C15 C14 130.03(14) . . ?
C20 C15 C14 111.65(13) . . ?
C17 C16 C15 119.52(15) . . ?
C17 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
C16 C17 C18 121.09(16) . . ?
C16 C17 H17 119.5 . . ?
C18 C17 H17 119.5 . . ?
C19 C18 C17 120.95(16) . . ?
C19 C18 H18 119.5 . . ?
C17 C18 H18 119.5 . . ?
C18 C19 C20 118.00(15) . . ?
C18 C19 H19 121.0 . . ?
C20 C19 H19 121.0 . . ?
C19 C20 C15 122.07(14) . . ?
C19 C20 S1 126.52(12) . . ?
C15 C20 S1 111.41(11) . . ?

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
C7 N1 N2 N3 0.35(16) . . . . ?
C6 N1 N2 N3 176.36(12) . . . . ?
N1 N2 N3 C9 0.01(15) . . . . ?
C6 C1 C2 C3 -1.4(2) . . . . ?
Cl1 C1 C2 C3 177.50(11) . . . . ?
C1 C2 C3 C4 0.4(2) . . . . ?
C1 C2 C3 Cl2 -179.99(11) . . . . ?
C2 C3 C4 C5 0.7(2) . . . . ?
Cl2 C3 C4 C5 -178.89(11) . . . . ?
C3 C4 C5 C6 -0.8(2) . . . . ?
C3 C4 C5 Cl3 179.12(12) . . . . ?
C2 C1 C6 C5 1.3(2) . . . . ?
Cl1 C1 C6 C5 -177.65(11) . . . . ?
C2 C1 C6 N1 178.56(13) . . . . ?
Cl1 C1 C6 N1 -0.39(19) . . . . ?
C4 C5 C6 C1 -0.1(2) . . . . ?
Cl3 C5 C6 C1 179.92(11) . . . . ?
C4 C5 C6 N1 -177.41(13) . . . . ?
Cl3 C5 C6 N1 2.63(19) . . . . ?
C7 N1 C6 C1 -85.24(18) . . . . ?
N2 N1 C6 C1 99.41(16) . . . . ?
C7 N1 C6 C5 91.98(18) . . . . ?
N2 N1 C6 C5 -83.37(17) . . . . ?
N2 N1 C7 C9 -0.55(15) . . . . ?
C6 N1 C7 C9 -176.28(13) . . . . ?
N2 N1 C7 C8 178.15(13) . . . . ?
C6 N1 C7 C8 2.4(2) . . . . ?
N2 N3 C9 C7 -0.35(16) . . . . ?
N2 N3 C9 C10 178.50(13) . . . . ?
N1 C7 C9 N3 0.54(15) . . . . ?
C8 C7 C9 N3 -177.95(15) . . . . ?
N1 C7 C9 C10 -178.25(13) . . . . ?
C8 C7 C9 C10 3.3(3) . . . . ?
N3 C9 C10 O1 -166.92(14) . . . . ?
C7 C9 C10 O1 11.7(2) . . . . ?
N3 C9 C10 C11 12.3(2) . . . . ?
C7 C9 C10 C11 -169.12(14) . . . . ?
O1 C10 C11 C12 3.5(2) . . . . ?
C9 C10 C11 C12 -175.69(14) . . . . ?
C10 C11 C12 C13 178.05(13) . . . . ?
C11 C12 C13 C14 -174.44(15) . . . . ?
C11 C12 C13 S1 3.5(2) . . . . ?
C20 S1 C13 C14 -1.18(12) . . . . ?
C20 S1 C13 C12 -179.37(12) . . . . ?
C12 C13 C14 C15 178.15(14) . . . . ?
S1 C13 C14 C15 0.10(17) . . . . ?
C13 C14 C15 C16 -178.50(16) . . . . ?
C13 C14 C15 C20 1.38(19) . . . . ?
C20 C15 C16 C17 1.1(2) . . . . ?
C14 C15 C16 C17 -178.97(16) . . . . ?
C15 C16 C17 C18 0.8(3) . . . . ?
C16 C17 C18 C19 -1.6(3) . . . . ?
C17 C18 C19 C20 0.3(3) . . . . ?
C18 C19 C20 C15 1.7(2) . . . . ?
C18 C19 C20 S1 -178.43(13) . . . . ?
C16 C15 C20 C19 -2.5(2) . . . . ?
C14 C15 C20 C19 177.64(14) . . . . ?
C16 C15 C20 S1 177.66(12) . . . . ?
C14 C15 C20 S1 -2.23(16) . . . . ?
C13 S1 C20 C19 -177.92(15) . . . . ?
C13 S1 C20 C15 1.95(12) . . . . ?

_refine_diff_density_max         0.282
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.043

