# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_skb_ta_06_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2239889'
loop_
_audit_author_name
_audit_author_address
'Dilip K. Maiti'
;University of Calcutta
India
;
_audit_update_record             
;
2023-02-04 deposited with the CCDC.	2023-03-22 downloaded from the CCDC.
;
_audit_creation_date             2023-01-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H15 N O S2'
_chemical_formula_sum            'C14 H15 N O S2'
_chemical_formula_weight         277.39
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_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                   15.095(9)
_cell_length_b                   7.738(5)
_cell_length_c                   11.649(7)
_cell_angle_alpha                90
_cell_angle_beta                 91.42(2)
_cell_angle_gamma                90
_cell_volume                     1360.1(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9231
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.80
_cell_measurement_theta_min      2.69
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.378
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6162
_exptl_absorpt_correction_type   EMPIRICAL
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1465 before and 0.0787 after correction.
The Ratio of minimum to maximum transmission is 0.8267.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.19
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0548
_diffrn_reflns_av_unetI/netI     0.0202
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            41655
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.941
_diffrn_reflns_theta_min         2.700
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2504
_reflns_number_total             2920
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.298
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2920
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0499
_refine_ls_R_factor_gt           0.0410
_refine_ls_restrained_S_all      1.081
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0517P)²+0.6925P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1109
_refine_ls_wR_factor_ref         0.1219
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00B(H00B)
2.b Secondary CH2 refined with riding coordinates:
 C00F(H00F,H00G), C00H(H00K,H00L), C00I(H00M,H00N)
2.c Aromatic/amide H refined with riding coordinates:
 C008(H008), C00A(H00A), C00C(H00C), C00D(H00D), C00E(H00E)
2.d Idealised Me refined as rotating group:
 C00G(H00H,H00I,H00J)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
S01 S 0.45943(4) 0.47395(8) 0.86706(5) 0.05800(19) Uani 1 1 d . . . . .
S02 S 0.43512(4) 0.41447(8) 0.61224(5) 0.0630(2) Uani 1 1 d . . . . .
O003 O 0.29243(10) 0.5905(2) 0.93022(12) 0.0587(4) Uani 1 1 d . . . . .
N004 N 0.26879(12) 0.5211(2) 0.62559(15) 0.0536(4) Uani 1 1 d . . . . .
C005 C 0.18250(12) 0.7173(3) 0.81205(16) 0.0450(4) Uani 1 1 d . . . . .
C006 C 0.26410(13) 0.6114(3) 0.83157(16) 0.0449(4) Uani 1 1 d . . . . .
C007 C 0.31006(13) 0.5394(2) 0.73555(16) 0.0445(4) Uani 1 1 d . . . . .
C008 C 0.16956(14) 0.8226(3) 0.71781(18) 0.0542(5) Uani 1 1 d . . . . .
H008 H 0.209874 0.820997 0.658731 0.065 Uiso 1 1 calc R . . . .
C009 C 0.39517(13) 0.4809(2) 0.74266(18) 0.0463(4) Uani 1 1 d . . . . .
C00A C 0.12080(14) 0.7198(3) 0.89833(18) 0.0566(5) Uani 1 1 d . . . . .
H00A H 0.129221 0.650164 0.962752 0.068 Uiso 1 1 calc R . . . .
C00B C 0.33417(16) 0.5049(3) 0.53857(18) 0.0585(6) Uani 1 1 d . . . . .
H00B H 0.347199 0.618221 0.505482 0.070 Uiso 1 1 calc R . . . .
C00C C 0.09670(18) 0.9306(3) 0.7110(2) 0.0670(6) Uani 1 1 d . . . . .
H00C H 0.089068 1.004036 0.648276 0.080 Uiso 1 1 calc R . . . .
C00D C 0.04737(16) 0.8242(4) 0.8895(2) 0.0709(7) Uani 1 1 d . . . . .
H00D H 0.005670 0.822916 0.946893 0.085 Uiso 1 1 calc R . . . .
C00E C 0.03543(17) 0.9301(4) 0.7964(2) 0.0707(7) Uani 1 1 d . . . . .
H00E H -0.014021 1.001530 0.790882 0.085 Uiso 1 1 calc R . . . .
C00F C 0.2935(2) 0.3865(4) 0.4475(2) 0.0808(9) Uani 1 1 d . . . . .
H00F H 0.272863 0.452479 0.381357 0.097 Uiso 1 1 calc R . . . .
H00G H 0.336496 0.301947 0.422699 0.097 Uiso 1 1 calc R . . . .
C00G C 0.56964(16) 0.4462(4) 0.8159(3) 0.0758(7) Uani 1 1 d . . . . .
H00H H 0.583966 0.540764 0.766296 0.114 Uiso 1 1 calc GR . . . .
H00I H 0.573038 0.339653 0.773994 0.114 Uiso 1 1 calc GR . . . .
H00J H 0.610883 0.443376 0.879903 0.114 Uiso 1 1 calc GR . . . .
C00H C 0.2090(2) 0.3717(5) 0.6149(3) 0.1007(12) Uani 1 1 d . . . . .
H00K H 0.224168 0.286211 0.672970 0.121 Uiso 1 1 calc R . . . .
H00L H 0.148207 0.407852 0.625380 0.121 Uiso 1 1 calc R . . . .
C00I C 0.2183(3) 0.3003(5) 0.5039(3) 0.1165(14) Uani 1 1 d . . . . .
H00M H 0.164252 0.317604 0.458659 0.140 Uiso 1 1 calc R . . . .
H00N H 0.229372 0.177092 0.509721 0.140 Uiso 1 1 calc R . . . .


_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
S01 C009 1.725(2) . ?
S01 C00G 1.794(3) . ?
S02 C009 1.727(2) . ?
S02 C00B 1.866(2) . ?
O003 C006 1.227(2) . ?
N004 C007 1.418(3) . ?
N004 C00B 1.438(3) . ?
N004 C00H 1.470(4) . ?
C005 C006 1.492(3) . ?
C005 C008 1.377(3) . ?
C005 C00A 1.387(3) . ?
C006 C007 1.442(3) . ?
C007 C009 1.363(3) . ?
C008 C00C 1.382(3) . ?
C00A C00D 1.373(3) . ?
C00B C00F 1.519(4) . ?
C00C C00E 1.375(4) . ?
C00D C00E 1.367(4) . ?
C00F C00I 1.484(5) . ?
C00H C00I 1.416(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
C009 S01 C00G 103.37(13) . . ?
C009 S02 C00B 89.66(10) . . ?
C007 N004 C00B 110.60(18) . . ?
C007 N004 C00H 114.2(2) . . ?
C00B N004 C00H 107.6(2) . . ?
C008 C005 C006 123.15(18) . . ?
C008 C005 C00A 119.00(19) . . ?
C00A C005 C006 117.62(18) . . ?
O003 C006 C005 118.84(18) . . ?
O003 C006 C007 120.81(18) . . ?
C007 C006 C005 120.32(17) . . ?
N004 C007 C006 122.01(17) . . ?
C009 C007 N004 114.47(18) . . ?
C009 C007 C006 123.50(18) . . ?
C005 C008 C00C 120.1(2) . . ?
S01 C009 S02 121.91(12) . . ?
C007 C009 S01 124.83(16) . . ?
C007 C009 S02 113.25(16) . . ?
C00D C00A C005 120.6(2) . . ?
N004 C00B S02 106.00(15) . . ?
N004 C00B C00F 105.8(2) . . ?
C00F C00B S02 113.95(16) . . ?
C00E C00C C008 120.3(2) . . ?
C00E C00D C00A 120.2(2) . . ?
C00D C00E C00C 119.9(2) . . ?
C00I C00F C00B 105.2(2) . . ?
C00I C00H N004 108.0(3) . . ?
C00H C00I C00F 108.9(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_dkmsam0290_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2239890'
loop_
_audit_author_name
_audit_author_address
'Dilip K. Maiti'
;University of Calcutta
India
;
_audit_update_record             
;
2023-02-04 deposited with the CCDC.	2023-03-22 downloaded from the CCDC.
;
_audit_creation_date             2023-01-13
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C H Cl3, C21 H17 N3 O5'
_chemical_formula_sum            'C22 H18 Cl3 N3 O5'
_chemical_formula_weight         510.74
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_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                   13.558(3)
_cell_length_b                   7.3045(19)
_cell_length_c                   23.523(6)
_cell_angle_alpha                90
_cell_angle_beta                 103.417(4)
_cell_angle_gamma                90
_cell_volume                     2266.0(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6851
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      24.05
_cell_measurement_theta_min      2.76
_shelx_estimated_absorpt_T_max   0.957
_shelx_estimated_absorpt_T_min   0.874
_exptl_absorpt_coefficient_mu    0.445
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6713
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0964 before and 0.0589 after correction.
The Ratio of minimum to maximum transmission is 0.9008.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light brown'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.497
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1048
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0641
_diffrn_reflns_av_unetI/netI     0.0283
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            54251
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.874
_diffrn_reflns_theta_min         1.593
_diffrn_ambient_temperature      298
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.35
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3018
_reflns_number_total             4357
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.466
_refine_diff_density_min         -0.573
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         4357
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0768
_refine_ls_R_factor_gt           0.0492
_refine_ls_restrained_S_all      1.011
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0528P)²+1.9845P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1151
_refine_ls_wR_factor_ref         0.1347
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C23(H23)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C4(H4), C17(H17), C18(H18), C21(H21), C20(H20), C7(H7), C3(H3)
2.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 0.80429(6) 0.79856(13) 0.92350(3) 0.0694(3) Uani 1 1 d . . . . .
Cl3 Cl 0.74637(8) 1.0204(2) 0.82062(5) 0.1105(5) Uani 1 1 d . . . . .
Cl2 Cl 0.70273(10) 0.6351(2) 0.81594(5) 0.1185(5) Uani 1 1 d . . . . .
O4 O 0.47517(14) 0.9198(3) 0.80351(8) 0.0554(5) Uani 1 1 d . . . . .
O5 O 0.45815(15) 0.7694(3) 0.53734(8) 0.0611(6) Uani 1 1 d . . . . .
N3 N 0.19102(15) 0.8519(3) 0.83298(8) 0.0371(5) Uani 1 1 d . . . . .
N2 N 0.20773(15) 0.8758(3) 0.74190(9) 0.0407(5) Uani 1 1 d . . . . .
O3 O 0.36269(17) 0.9865(3) 0.92783(9) 0.0677(6) Uani 1 1 d . . . . .
C5 C 0.44547(18) 0.7163(3) 0.90956(10) 0.0350(5) Uani 1 1 d . . . . .
C9 C 0.29282(18) 0.8551(3) 0.83711(10) 0.0361(5) Uani 1 1 d . . . . .
C14 C 0.30217(18) 0.8695(3) 0.77990(10) 0.0363(5) Uani 1 1 d . . . . .
C16 C 0.41170(18) 0.8617(3) 0.70318(10) 0.0375(6) Uani 1 1 d . . . . .
O1 O 0.73190(18) 0.3262(4) 1.00122(13) 0.0935(9) Uani 1 1 d . . . . .
C6 C 0.43307(19) 0.5502(4) 0.88044(10) 0.0411(6) Uani 1 1 d . . . . .
H6 H 0.377422 0.532557 0.849338 0.049 Uiso 1 1 calc R U . . .
C15 C 0.40060(18) 0.8869(4) 0.76399(11) 0.0397(6) Uani 1 1 d . . . . .
N1 N 0.6593(2) 0.2950(5) 0.96065(13) 0.0696(8) Uani 1 1 d . . . . .
C13 C 0.14382(19) 0.8643(3) 0.77596(11) 0.0392(6) Uani 1 1 d . . . . .
C8 C 0.36810(19) 0.8636(4) 0.89410(10) 0.0398(6) Uani 1 1 d . . . . .
C4 C 0.52920(19) 0.7434(4) 0.95577(10) 0.0423(6) Uani 1 1 d . . . . .
H4 H 0.537917 0.854822 0.975413 0.051 Uiso 1 1 calc R U . . .
C17 C 0.33425(19) 0.8037(4) 0.65656(11) 0.0405(6) Uani 1 1 d . . . . .
H17 H 0.269785 0.782626 0.662577 0.049 Uiso 1 1 calc R U . . .
C18 C 0.3519(2) 0.7773(4) 0.60202(11) 0.0440(6) Uani 1 1 d . . . . .
H18 H 0.299241 0.739713 0.571397 0.053 Uiso 1 1 calc R U . . .
C2 C 0.58410(19) 0.4425(4) 0.94277(11) 0.0447(6) Uani 1 1 d . . . . .
C19 C 0.4482(2) 0.8065(4) 0.59223(11) 0.0421(6) Uani 1 1 d . . . . .
C21 C 0.50708(19) 0.8913(4) 0.69217(11) 0.0426(6) Uani 1 1 d . . . . .
H21 H 0.559768 0.929686 0.722630 0.051 Uiso 1 1 calc R U . . .
C20 C 0.5259(2) 0.8654(4) 0.63751(11) 0.0448(6) Uani 1 1 d . . . . .
H20 H 0.590125 0.887405 0.631247 0.054 Uiso 1 1 calc R U . . .
C10 C 0.12267(19) 0.8193(4) 0.87169(12) 0.0444(6) Uani 1 1 d . . . . .
H10A H 0.138050 0.899456 0.905479 0.053 Uiso 1 1 calc R U . . .
H10B H 0.125560 0.693013 0.884678 0.053 Uiso 1 1 calc R U . . .
C7 C 0.5023(2) 0.4108(4) 0.89699(11) 0.0486(7) Uani 1 1 d . . . . .
H7 H 0.493820 0.298619 0.877776 0.058 Uiso 1 1 calc R U . . .
C3 C 0.59890(19) 0.6060(4) 0.97242(11) 0.0472(7) Uani 1 1 d . . . . .
H3 H 0.655125 0.623150 1.003204 0.057 Uiso 1 1 calc R U . . .
C11 C 0.0188(2) 0.8653(4) 0.83126(12) 0.0497(7) Uani 1 1 d . . . . .
H11A H -0.031718 0.777020 0.836620 0.060 Uiso 1 1 calc R U . . .
H11B H -0.003054 0.986291 0.840153 0.060 Uiso 1 1 calc R U . . .
C12 C 0.03164(19) 0.8586(4) 0.76789(12) 0.0493(7) Uani 1 1 d . . . . .
H12A H 0.003436 0.746868 0.748425 0.059 Uiso 1 1 calc R U . . .
H12B H -0.000362 0.963065 0.745534 0.059 Uiso 1 1 calc R U . . .
O2 O 0.6434(3) 0.1489(5) 0.93555(14) 0.1179(12) Uani 1 1 d . . . . .
C23 C 0.7143(2) 0.8328(5) 0.85828(13) 0.0615(8) Uani 1 1 d . . . . .
H23 H 0.648785 0.857557 0.867609 0.074 Uiso 1 1 calc R U . . .
C22 C 0.5577(3) 0.7785(6) 0.52608(14) 0.0723(10) Uani 1 1 d . . . . .
H22A H 0.554275 0.744751 0.486223 0.108 Uiso 1 1 calc R U . . .
H22B H 0.602066 0.695832 0.551714 0.108 Uiso 1 1 calc R U . . .
H22C H 0.583371 0.901056 0.532770 0.108 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 C23 1.742(3) . ?
Cl3 C23 1.741(4) . ?
Cl2 C23 1.740(4) . ?
O4 C15 1.228(3) . ?
O5 C19 1.356(3) . ?
O5 C22 1.436(4) . ?
N3 C9 1.361(3) . ?
N3 C13 1.349(3) . ?
N3 C10 1.461(3) . ?
N2 C14 1.382(3) . ?
N2 C13 1.312(3) . ?
O3 C8 1.212(3) . ?
C5 C6 1.384(3) . ?
C5 C8 1.488(3) . ?
C5 C4 1.392(3) . ?
C9 C14 1.385(3) . ?
C9 C8 1.486(3) . ?
C14 C15 1.473(4) . ?
C16 C15 1.484(3) . ?
C16 C17 1.396(3) . ?
C16 C21 1.393(4) . ?
O1 N1 1.222(4) . ?
C6 H6 0.9300 . ?
C6 C7 1.378(4) . ?
N1 C2 1.476(4) . ?
N1 O2 1.215(4) . ?
C13 C12 1.489(4) . ?
C4 H4 0.9300 . ?
C4 C3 1.372(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.372(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.394(4) . ?
C2 C7 1.375(4) . ?
C2 C3 1.374(4) . ?
C19 C20 1.382(4) . ?
C21 H21 0.9300 . ?
C21 C20 1.381(4) . ?
C20 H20 0.9300 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.542(4) . ?
C7 H7 0.9300 . ?
C3 H3 0.9300 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.541(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C23 H23 0.9800 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C19 O5 C22 118.1(2) . . ?
C9 N3 C10 137.5(2) . . ?
C13 N3 C9 108.0(2) . . ?
C13 N3 C10 114.0(2) . . ?
C13 N2 C14 104.3(2) . . ?
C6 C5 C8 121.0(2) . . ?
C6 C5 C4 119.6(2) . . ?
C4 C5 C8 119.3(2) . . ?
N3 C9 C14 104.59(19) . . ?
N3 C9 C8 122.6(2) . . ?
C14 C9 C8 132.5(2) . . ?
N2 C14 C9 110.6(2) . . ?
N2 C14 C15 126.2(2) . . ?
C9 C14 C15 123.1(2) . . ?
C17 C16 C15 124.6(2) . . ?
C21 C16 C15 117.8(2) . . ?
C21 C16 C17 117.5(2) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 C5 120.8(2) . . ?
C7 C6 H6 119.6 . . ?
O4 C15 C14 117.4(2) . . ?
O4 C15 C16 120.3(2) . . ?
C14 C15 C16 122.3(2) . . ?
O1 N1 C2 117.7(3) . . ?
O2 N1 O1 124.3(3) . . ?
O2 N1 C2 118.0(3) . . ?
N3 C13 C12 111.1(2) . . ?
N2 C13 N3 112.5(2) . . ?
N2 C13 C12 136.4(2) . . ?
O3 C8 C5 121.5(2) . . ?
O3 C8 C9 119.2(2) . . ?
C9 C8 C5 119.2(2) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 C5 120.1(3) . . ?
C3 C4 H4 119.9 . . ?
C16 C17 H17 119.5 . . ?
C18 C17 C16 121.0(2) . . ?
C18 C17 H17 119.5 . . ?
C17 C18 H18 119.8 . . ?
C17 C18 C19 120.4(2) . . ?
C19 C18 H18 119.8 . . ?
C7 C2 N1 118.6(3) . . ?
C3 C2 N1 118.7(3) . . ?
C3 C2 C7 122.7(2) . . ?
O5 C19 C18 115.5(2) . . ?
O5 C19 C20 124.7(2) . . ?
C20 C19 C18 119.7(2) . . ?
C16 C21 H21 118.9 . . ?
C20 C21 C16 122.1(2) . . ?
C20 C21 H21 118.9 . . ?
C19 C20 H20 120.4 . . ?
C21 C20 C19 119.2(2) . . ?
C21 C20 H20 120.4 . . ?
N3 C10 H10A 111.5 . . ?
N3 C10 H10B 111.5 . . ?
N3 C10 C11 101.6(2) . . ?
H10A C10 H10B 109.3 . . ?
C11 C10 H10A 111.5 . . ?
C11 C10 H10B 111.5 . . ?
C6 C7 H7 121.0 . . ?
C2 C7 C6 118.0(3) . . ?
C2 C7 H7 121.0 . . ?
C4 C3 C2 118.8(2) . . ?
C4 C3 H3 120.6 . . ?
C2 C3 H3 120.6 . . ?
C10 C11 H11A 110.3 . . ?
C10 C11 H11B 110.3 . . ?
H11A C11 H11B 108.5 . . ?
C12 C11 C10 107.3(2) . . ?
C12 C11 H11A 110.3 . . ?
C12 C11 H11B 110.3 . . ?
C13 C12 C11 102.5(2) . . ?
C13 C12 H12A 111.3 . . ?
C13 C12 H12B 111.3 . . ?
C11 C12 H12A 111.3 . . ?
C11 C12 H12B 111.3 . . ?
H12A C12 H12B 109.2 . . ?
Cl1 C23 H23 108.4 . . ?
Cl3 C23 Cl1 110.77(18) . . ?
Cl3 C23 H23 108.4 . . ?
Cl2 C23 Cl1 109.66(19) . . ?
Cl2 C23 Cl3 111.22(18) . . ?
Cl2 C23 H23 108.4 . . ?
O5 C22 H22A 109.5 . . ?
O5 C22 H22B 109.5 . . ?
O5 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O5 C19 C20 C21 -177.3(3) . . . . ?
N3 C9 C14 N2 0.3(3) . . . . ?
N3 C9 C14 C15 176.8(2) . . . . ?
N3 C9 C8 O3 -55.4(4) . . . . ?
N3 C9 C8 C5 121.8(3) . . . . ?
N3 C13 C12 C11 7.0(3) . . . . ?
N3 C10 C11 C12 18.4(3) . . . . ?
N2 C14 C15 O4 163.8(3) . . . . ?
N2 C14 C15 C16 -17.7(4) . . . . ?
N2 C13 C12 C11 -174.1(3) . . . . ?
C5 C6 C7 C2 -0.6(4) . . . . ?
C5 C4 C3 C2 -0.2(4) . . . . ?
C9 N3 C13 N2 -0.1(3) . . . . ?
C9 N3 C13 C12 179.1(2) . . . . ?
C9 N3 C10 C11 173.8(3) . . . . ?
C9 C14 C15 O4 -12.2(4) . . . . ?
C9 C14 C15 C16 166.3(2) . . . . ?
C14 N2 C13 N3 0.3(3) . . . . ?
C14 N2 C13 C12 -178.7(3) . . . . ?
C14 C9 C8 O3 116.1(3) . . . . ?
C14 C9 C8 C5 -66.6(4) . . . . ?
C16 C17 C18 C19 0.6(4) . . . . ?
C16 C21 C20 C19 -0.7(4) . . . . ?
O1 N1 C2 C7 179.6(3) . . . . ?
O1 N1 C2 C3 -0.2(4) . . . . ?
C6 C5 C8 O3 159.7(3) . . . . ?
C6 C5 C8 C9 -17.4(4) . . . . ?
C6 C5 C4 C3 -0.1(4) . . . . ?
C15 C16 C17 C18 -177.6(2) . . . . ?
C15 C16 C21 C20 177.8(2) . . . . ?
N1 C2 C7 C6 -179.4(2) . . . . ?
N1 C2 C3 C4 179.8(2) . . . . ?
C13 N3 C9 C14 -0.1(3) . . . . ?
C13 N3 C9 C8 173.4(2) . . . . ?
C13 N3 C10 C11 -15.0(3) . . . . ?
C13 N2 C14 C9 -0.3(3) . . . . ?
C13 N2 C14 C15 -176.8(2) . . . . ?
C8 C5 C6 C7 -176.5(2) . . . . ?
C8 C5 C4 C3 177.0(2) . . . . ?
C8 C9 C14 N2 -172.3(3) . . . . ?
C8 C9 C14 C15 4.2(4) . . . . ?
C4 C5 C6 C7 0.5(4) . . . . ?
C4 C5 C8 O3 -17.3(4) . . . . ?
C4 C5 C8 C9 165.5(2) . . . . ?
C17 C16 C15 O4 172.4(3) . . . . ?
C17 C16 C15 C14 -6.1(4) . . . . ?
C17 C16 C21 C20 0.1(4) . . . . ?
C17 C18 C19 O5 177.5(2) . . . . ?
C17 C18 C19 C20 -1.1(4) . . . . ?
C18 C19 C20 C21 1.2(4) . . . . ?
C21 C16 C15 O4 -5.1(4) . . . . ?
C21 C16 C15 C14 176.4(2) . . . . ?
C21 C16 C17 C18 -0.1(4) . . . . ?
C10 N3 C9 C14 171.4(3) . . . . ?
C10 N3 C9 C8 -15.0(4) . . . . ?
C10 N3 C13 N2 -173.9(2) . . . . ?
C10 N3 C13 C12 5.3(3) . . . . ?
C10 C11 C12 C13 -15.8(3) . . . . ?
C7 C2 C3 C4 0.0(4) . . . . ?
C3 C2 C7 C6 0.3(4) . . . . ?
O2 N1 C2 C7 -2.9(4) . . . . ?
O2 N1 C2 C3 177.3(3) . . . . ?
C22 O5 C19 C18 -173.7(3) . . . . ?
C22 O5 C19 C20 4.8(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
