# 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_AM14
_database_code_depnum_ccdc_archive 'CCDC 2385195'
loop_
_audit_author_name
_audit_author_address
'Aida Ildusovna Samigullina'
;N D Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2024-09-19 deposited with the CCDC.	2025-03-24 downloaded from the CCDC.
;
_audit_creation_date             2024-02-29
_audit_creation_method           
;
Olex2 1.3
(compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r5938)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H20 N2 O4 S'
_chemical_formula_sum            'C21 H20 N2 O4 S'
_chemical_formula_weight         396.45
_chemical_melting_point          ?
_chemical_oxdiff_formula         C21H20N2O4S
_chemical_oxdiff_usercomment     AM14
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   13.2397(3)
_cell_length_b                   19.0851(4)
_cell_length_c                   6.99979(12)
_cell_angle_alpha                90
_cell_angle_beta                 93.8020(18)
_cell_angle_gamma                90
_cell_volume                     1764.82(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4335
_cell_measurement_temperature    100.00(11)
_cell_measurement_theta_max      79.0890
_cell_measurement_theta_min      4.0880
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.911
_exptl_absorpt_correction_T_max  0.966
_exptl_absorpt_correction_T_min  0.736
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.104a (Rigaku Oxford Diffraction, 2023)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Spherical absorption correction
using equivalent radius and absorption coefficient.
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.492
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             832
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 0 0.0604
0 1 0 0.0664
1 0 -1 0.0995
-1 0 1 0.0936
-1 0 0 0.0102
1 0 0 0.0082

_exptl_crystal_size_max          0.221
_exptl_crystal_size_mid          0.127
_exptl_crystal_size_min          0.018
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.0010 -1.0001 -0.0001 -0.0565 -0.0482 -0.0317
0.0010 1.0001 0.0001 0.0565 0.0482 0.0317
1.0018 -0.0021 -0.9992 -0.0876 -0.0433 0.2218
-1.0018 0.0021 0.9992 0.0876 0.0433 -0.2218
-0.9998 0.0017 -0.0010 0.0829 -0.0741 -0.0352
0.9998 -0.0017 0.0010 -0.0829 0.0741 0.0352

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0107
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            6297
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.968
_diffrn_reflns_theta_min         3.345
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(11)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -80.00  34.00   0.50    4.50    --  -40.36  92.00 -83.00  228
  2  ω     -8.00  27.00   0.50    4.50    --   40.36 -92.00 163.00   70
  3  ω     31.00  80.00   0.50    4.50    --   40.36 -92.00 163.00   98
  4  ω   -152.00-127.00   0.50   14.00    --  -98.00 -92.00 163.00   50
  5  ω    106.00 168.00   0.50   14.00    --  119.50  92.00 -83.00  124
  6  ω     51.00  76.00   0.50   14.00    --  119.50 -92.00 163.00   50
  7  ω    -27.00  32.00   0.50    4.50    --  -40.36  19.00 -90.00  118
  8  ω    -27.00  38.00   0.50    4.50    --  -40.36  19.00  30.00  130
  9  ω    -45.00  37.00   0.50    4.50    --  -40.36  92.00 -83.00  164
 10  ω     71.00 119.00   0.50    4.50    --   40.36 178.00-150.00   96
 11  ω    -51.00 -26.00   0.50   14.00    --  -98.00  45.00 120.00   50
 12  ω    -50.00 -21.00   0.50   14.00    --  -98.00  45.00 -60.00   58
 13  ω    -74.00 -48.00   0.50   14.00    --  -98.00  92.00 -83.00   52
 14  ω    -50.00 -25.00   0.50   14.00    --  -98.00  45.00 150.00   50
 15  ω    -50.00 -21.00   0.50   14.00    --  -98.00  45.00  90.00   58
 16  ω     82.00 107.00   0.50   14.00    --  119.50-111.00  90.00   50
 17  ω     47.00  73.00   0.50   14.00    --  119.50 -95.00 120.00   52
 18  ω    103.00 129.00   0.50   14.00    --  119.50  45.00  30.00   52
 19  ω     74.00 100.00   0.50   14.00    --  119.50 -95.00 120.00   52
 20  ω     69.00 100.00   0.50   14.00    --  119.50 -80.00 -13.44   62
 21  ω     71.00 102.00   0.50   14.00    --  119.50-111.00 -30.00   62
 22  ω     46.00  74.00   0.50   14.00    --  119.50-111.00  90.00   56
 23  ω    126.00 152.00   0.50   14.00    --  119.50 111.00-150.00   52
 24  ω     55.00  96.00   0.50   14.00    --  119.50 -77.00   0.00   82
 25  ω    151.00 177.00   0.50   14.00    --  119.50 111.00-180.00   52
 26  ω     68.00 108.00   0.50   14.00    --  119.50-111.00 120.00   80
 27  ω     94.00 137.00   0.50   14.00    --  119.50  61.00 120.00   86
 28  ω    145.00 170.00   0.50   14.00    --  119.50  61.00 120.00   50
 29  ω     87.00 135.00   0.50   14.00    --  119.50  77.00 -60.00   96
 30  ω     93.00 141.00   0.50   14.00    --  119.50  61.00  60.00   96
 31  ω     47.00  98.00   0.50   14.00    --  119.50-111.00-120.00  102
 32  ω     89.00 141.00   0.50   14.00    --  119.50  77.00-120.00  104
 33  ω    144.00 170.00   0.50   14.00    --  119.50  77.00-120.00   52
 34  ω    139.00 177.00   0.50   14.00    --  119.50 111.00 150.00   76
 35  ω     80.00 105.00   0.50   14.00    --  119.50 -77.00-180.00   50
 36  ω    129.00 154.00   0.50   14.00    --  119.50 -80.00 -13.44   50
 37  ω     80.00 105.00   0.50   14.00    --  119.50 -95.00-180.00   50
 38  ω    124.00 165.00   0.50   14.00    --  119.50 111.00 -60.00   82
 39  ω     42.00  74.00   0.50   14.00    --  119.50 -95.00-180.00   64
 40  ω    104.00 143.00   0.50   14.00    --  119.50 178.00  60.00   78
 41  ω    128.00 157.00   0.50   14.00    --  119.50 -87.00  85.58   58
 42  ω     64.00 146.00   0.50   14.00    --  119.50 178.00-180.00  164
 43  ω     76.00 102.00   0.50   14.00    --  119.50 -87.00  85.58   52
 44  ω    103.00 131.00   0.50   14.00    --  119.50 111.00-180.00   56
 45  ω     90.00 163.00   0.50   14.00    --  119.50  30.00  90.00  146
 46  ω    104.00 152.00   0.50   14.00    --  119.50 -88.00  81.03   96
 47  ω    104.00 177.00   0.50   14.00    --  119.50  61.00   0.00  146
 48  ω     65.00  91.00   0.50   14.00    --  119.50 -82.00 157.04   52
 49  ω    119.00 155.00   0.50   14.00    --  119.50 -82.00 157.04   72
 50  ω     73.00  98.00   0.50   14.00    --  119.50 -84.00-138.26   50
 51  ω     95.00 155.00   0.50   14.00    --  119.50  61.00-120.00  120
 52  ω     95.00 133.00   0.50   14.00    --  119.50  45.00 -30.00   76
 53  ω     49.00  85.00   0.50   14.00    --  119.50 -77.00-120.00   72
 54  ω     53.00 104.00   0.50   14.00    --  119.50 -95.00 -30.00  102
 55  ω    145.00 177.00   0.50   14.00    --  119.50  77.00 -60.00   64
 56  ω    115.00 141.00   0.50   14.00    --  119.50  30.00-180.00   52
 57  ω     44.00  73.00   0.50   14.00    --  119.50 -84.00 107.59   58
 58  ω    115.00 153.00   0.50   14.00    --  119.50 -84.00 107.59   76
 59  ω     63.00  89.00   0.50   14.00    --  119.50 -88.00 -20.02   52
 60  ω     48.00  75.00   0.50   14.00    --  119.50 -95.00-120.00   54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0828535000
_diffrn_orient_matrix_UB_12      0.0565793000
_diffrn_orient_matrix_UB_13      0.0044966000
_diffrn_orient_matrix_UB_21      0.0740304000
_diffrn_orient_matrix_UB_22      0.0481004000
_diffrn_orient_matrix_UB_23      0.1174682000
_diffrn_orient_matrix_UB_31      0.0353974000
_diffrn_orient_matrix_UB_32      0.0316866000
_diffrn_orient_matrix_UB_33      -0.1865850000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5856
_reflns_number_total             6297
_reflns_special_details          
;
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.43.104a (Rigaku OD, 2023)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.104a 64-bit (release 22-12-2023))'
_computing_data_reduction        'CrysAlisPro 1.171.43.104a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.426
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         6297
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0517
_refine_ls_R_factor_gt           0.0489
_refine_ls_restrained_S_all      1.046
_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)+(0.0822P)²+1.2035P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1392
_refine_ls_wR_factor_ref         0.1419
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.4532(14)
 0.5468(14)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C9(H9), C13(H13)
3.b Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C24(H24A,H24B,
 H24C), C25(H25A,H25B,H25C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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 0.27041(4) 0.30855(3) 0.27862(9) 0.02138(16) Uani 1 1 d . . . . .
O8 O 0.86977(12) 0.36359(9) 0.2362(3) 0.0298(4) Uani 1 1 d . . . . .
O12 O 0.62779(12) 0.53382(8) 0.2198(3) 0.0313(4) Uani 1 1 d . . . . .
O15 O 0.34147(12) 0.46076(8) 0.2673(3) 0.0224(3) Uani 1 1 d . . . . .
O19 O 0.11997(12) 0.22063(9) 0.2726(3) 0.0301(4) Uani 1 1 d . . . . .
N3 N 0.42572(14) 0.22343(10) 0.2916(3) 0.0229(4) Uani 1 1 d . . . . .
N18 N 0.27030(14) 0.16494(10) 0.2837(3) 0.0224(4) Uani 1 1 d . . . . .
H18 H 0.304(3) 0.1256(18) 0.282(5) 0.040(9) Uiso 1 1 d . . . . .
C2 C 0.32709(17) 0.22541(11) 0.2865(4) 0.0216(4) Uani 1 1 d . . . . .
C4 C 0.46352(17) 0.29067(12) 0.2861(3) 0.0221(4) Uani 1 1 d . . . . .
C5 C 0.56889(17) 0.30796(11) 0.2826(3) 0.0222(5) Uani 1 1 d . . . . .
C6 C 0.64420(19) 0.25623(13) 0.3030(4) 0.0266(5) Uani 1 1 d . . . . .
H6 H 0.625107 0.209140 0.325817 0.032 Uiso 1 1 calc R U . . .
C7 C 0.74506(18) 0.27201(12) 0.2907(4) 0.0263(5) Uani 1 1 d . . . . .
H7 H 0.795043 0.236351 0.305456 0.032 Uiso 1 1 calc R U . . .
C8 C 0.77284(17) 0.34152(12) 0.2559(3) 0.0243(5) Uani 1 1 d . . . . .
C9 C 0.70047(18) 0.39393(12) 0.2402(4) 0.0233(5) Uani 1 1 d . . . . .
H9 H 0.720896 0.440764 0.217691 0.028 Uiso 1 1 calc R U . . .
C10 C 0.59715(17) 0.37921(12) 0.2569(3) 0.0213(5) Uani 1 1 d . . . . .
C11 C 0.51993(18) 0.43403(12) 0.2505(3) 0.0214(5) Uani 1 1 d . . . . .
C12 C 0.54179(17) 0.50943(12) 0.2386(4) 0.0226(5) Uani 1 1 d . . . . .
C13 C 0.45545(19) 0.55512(12) 0.2480(4) 0.0245(5) Uani 1 1 d . . . . .
H13 H 0.465896 0.604344 0.244758 0.029 Uiso 1 1 calc R U . . .
C14 C 0.36169(18) 0.53113(11) 0.2611(3) 0.0229(5) Uani 1 1 d . . . . .
C16 C 0.42006(17) 0.41436(12) 0.2651(3) 0.0208(4) Uani 1 1 d . . . . .
C17 C 0.39150(17) 0.34343(12) 0.2780(3) 0.0216(4) Uani 1 1 d . . . . .
C19 C 0.16568(17) 0.16529(12) 0.2731(4) 0.0229(4) Uani 1 1 d . . . . .
C20 C 0.11257(17) 0.09406(12) 0.2629(4) 0.0237(5) Uani 1 1 d . . . . .
C21 C 0.14414(19) 0.05103(13) 0.4415(4) 0.0278(5) Uani 1 1 d . . . . .
H21A H 0.217685 0.044316 0.449497 0.042 Uiso 1 1 calc R U . . .
H21B H 0.110471 0.005291 0.433600 0.042 Uiso 1 1 calc R U . . .
H21C H 0.124483 0.075917 0.555732 0.042 Uiso 1 1 calc R U . . .
C22 C 0.1399(2) 0.05509(13) 0.0808(4) 0.0283(5) Uani 1 1 d . . . . .
H22A H 0.116932 0.082527 -0.032227 0.042 Uiso 1 1 calc R U . . .
H22B H 0.106621 0.009184 0.075580 0.042 Uiso 1 1 calc R U . . .
H22C H 0.213379 0.048754 0.083108 0.042 Uiso 1 1 calc R U . . .
C23 C -0.00223(18) 0.10530(13) 0.2538(4) 0.0300(5) Uani 1 1 d . . . . .
H23A H -0.020487 0.130909 0.367850 0.045 Uiso 1 1 calc R U . . .
H23B H -0.036528 0.059769 0.248662 0.045 Uiso 1 1 calc R U . . .
H23C H -0.023111 0.132411 0.138985 0.045 Uiso 1 1 calc R U . . .
C24 C 0.94757(18) 0.31145(12) 0.2456(4) 0.0275(5) Uani 1 1 d . . . . .
H24A H 0.931769 0.275618 0.147865 0.041 Uiso 1 1 calc R U . . .
H24B H 0.951632 0.289635 0.372626 0.041 Uiso 1 1 calc R U . . .
H24C H 1.012618 0.333367 0.222779 0.041 Uiso 1 1 calc R U . . .
C25 C 0.26708(17) 0.57325(12) 0.2688(4) 0.0262(5) Uani 1 1 d . . . . .
H25A H 0.231949 0.574890 0.141133 0.039 Uiso 1 1 calc R U . . .
H25B H 0.284234 0.620970 0.311238 0.039 Uiso 1 1 calc R U . . .
H25C H 0.222941 0.551554 0.358938 0.039 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 C2 1.755(2) . ?
S1 C17 1.736(2) . ?
O8 C8 1.366(3) . ?
O8 C24 1.431(3) . ?
O12 C12 1.245(3) . ?
O15 C14 1.371(3) . ?
O15 C16 1.367(3) . ?
O19 C19 1.217(3) . ?
N3 C2 1.305(3) . ?
N3 C4 1.379(3) . ?
N18 H18 0.88(3) . ?
N18 C2 1.377(3) . ?
N18 C19 1.382(3) . ?
C4 C5 1.435(3) . ?
C4 C17 1.385(3) . ?
C5 C6 1.404(3) . ?
C5 C10 1.425(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.377(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.402(3) . ?
C8 C9 1.384(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.409(3) . ?
C10 C11 1.461(3) . ?
C11 C12 1.471(3) . ?
C11 C16 1.385(3) . ?
C12 C13 1.443(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.332(3) . ?
C14 C25 1.492(3) . ?
C16 C17 1.410(3) . ?
C19 C20 1.530(3) . ?
C20 C21 1.530(3) . ?
C20 C22 1.540(3) . ?
C20 C23 1.532(3) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 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
C17 S1 C2 87.35(11) . . ?
C8 O8 C24 117.33(18) . . ?
C16 O15 C14 118.93(18) . . ?
C2 N3 C4 109.68(19) . . ?
C2 N18 H18 116(2) . . ?
C2 N18 C19 122.76(19) . . ?
C19 N18 H18 121(2) . . ?
N3 C2 S1 116.89(17) . . ?
N3 C2 N18 121.4(2) . . ?
N18 C2 S1 121.71(17) . . ?
N3 C4 C5 124.7(2) . . ?
N3 C4 C17 115.3(2) . . ?
C17 C4 C5 120.0(2) . . ?
C6 C5 C4 121.4(2) . . ?
C6 C5 C10 119.6(2) . . ?
C10 C5 C4 119.0(2) . . ?
C5 C6 H6 119.2 . . ?
C7 C6 C5 121.7(2) . . ?
C7 C6 H6 119.2 . . ?
C6 C7 H7 120.5 . . ?
C6 C7 C8 119.0(2) . . ?
C8 C7 H7 120.5 . . ?
O8 C8 C7 124.6(2) . . ?
O8 C8 C9 114.8(2) . . ?
C9 C8 C7 120.6(2) . . ?
C8 C9 H9 119.3 . . ?
C8 C9 C10 121.3(2) . . ?
C10 C9 H9 119.3 . . ?
C5 C10 C11 119.9(2) . . ?
C9 C10 C5 117.7(2) . . ?
C9 C10 C11 122.4(2) . . ?
C10 C11 C12 124.2(2) . . ?
C16 C11 C10 118.2(2) . . ?
C16 C11 C12 117.5(2) . . ?
O12 C12 C11 123.8(2) . . ?
O12 C12 C13 120.8(2) . . ?
C13 C12 C11 115.4(2) . . ?
C12 C13 H13 118.7 . . ?
C14 C13 C12 122.7(2) . . ?
C14 C13 H13 118.7 . . ?
O15 C14 C25 111.13(19) . . ?
C13 C14 O15 121.6(2) . . ?
C13 C14 C25 127.3(2) . . ?
O15 C16 C11 123.8(2) . . ?
O15 C16 C17 114.43(19) . . ?
C11 C16 C17 121.8(2) . . ?
C4 C17 S1 110.76(17) . . ?
C4 C17 C16 120.9(2) . . ?
C16 C17 S1 128.30(18) . . ?
O19 C19 N18 120.0(2) . . ?
O19 C19 C20 123.0(2) . . ?
N18 C19 C20 117.01(19) . . ?
C19 C20 C21 109.8(2) . . ?
C19 C20 C22 109.6(2) . . ?
C19 C20 C23 109.22(19) . . ?
C21 C20 C22 110.5(2) . . ?
C21 C20 C23 109.0(2) . . ?
C23 C20 C22 108.6(2) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O8 C24 H24A 109.5 . . ?
O8 C24 H24B 109.5 . . ?
O8 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C14 C25 H25A 109.5 . . ?
C14 C25 H25B 109.5 . . ?
C14 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N18 H18 O12 0.88(3) 1.97(3) 2.844(2) 176(3) 2_645 yes

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
O8 C8 C9 C10 179.8(2) . . . . ?
O12 C12 C13 C14 177.5(3) . . . . ?
O15 C16 C17 S1 5.1(3) . . . . ?
O15 C16 C17 C4 -177.1(2) . . . . ?
O19 C19 C20 C21 -119.8(3) . . . . ?
O19 C19 C20 C22 118.6(3) . . . . ?
O19 C19 C20 C23 -0.3(4) . . . . ?
N3 C4 C5 C6 -6.2(4) . . . . ?
N3 C4 C5 C10 173.5(2) . . . . ?
N3 C4 C17 S1 0.4(3) . . . . ?
N3 C4 C17 C16 -177.8(2) . . . . ?
N18 C19 C20 C21 60.0(3) . . . . ?
N18 C19 C20 C22 -61.6(3) . . . . ?
N18 C19 C20 C23 179.5(2) . . . . ?
C2 S1 C17 C4 -0.74(19) . . . . ?
C2 S1 C17 C16 177.2(2) . . . . ?
C2 N3 C4 C5 -177.7(2) . . . . ?
C2 N3 C4 C17 0.4(3) . . . . ?
C2 N18 C19 O19 -2.6(4) . . . . ?
C2 N18 C19 C20 177.6(2) . . . . ?
C4 N3 C2 S1 -1.0(3) . . . . ?
C4 N3 C2 N18 177.8(2) . . . . ?
C4 C5 C6 C7 176.9(2) . . . . ?
C4 C5 C10 C9 -175.5(2) . . . . ?
C4 C5 C10 C11 5.0(3) . . . . ?
C5 C4 C17 S1 178.54(19) . . . . ?
C5 C4 C17 C16 0.4(4) . . . . ?
C5 C6 C7 C8 -0.3(4) . . . . ?
C5 C10 C11 C12 175.4(2) . . . . ?
C5 C10 C11 C16 -1.6(3) . . . . ?
C6 C5 C10 C9 4.2(3) . . . . ?
C6 C5 C10 C11 -175.2(2) . . . . ?
C6 C7 C8 O8 -178.4(2) . . . . ?
C6 C7 C8 C9 2.0(4) . . . . ?
C7 C8 C9 C10 -0.5(4) . . . . ?
C8 C9 C10 C5 -2.6(4) . . . . ?
C8 C9 C10 C11 176.8(2) . . . . ?
C9 C10 C11 C12 -4.0(4) . . . . ?
C9 C10 C11 C16 179.0(2) . . . . ?
C10 C5 C6 C7 -2.8(4) . . . . ?
C10 C11 C12 O12 5.0(4) . . . . ?
C10 C11 C12 C13 -175.6(2) . . . . ?
C10 C11 C16 O15 177.8(2) . . . . ?
C10 C11 C16 C17 -2.6(4) . . . . ?
C11 C12 C13 C14 -1.8(4) . . . . ?
C11 C16 C17 S1 -174.57(19) . . . . ?
C11 C16 C17 C4 3.2(4) . . . . ?
C12 C11 C16 O15 0.6(4) . . . . ?
C12 C11 C16 C17 -179.7(2) . . . . ?
C12 C13 C14 O15 0.3(4) . . . . ?
C12 C13 C14 C25 -179.0(2) . . . . ?
C14 O15 C16 C11 -2.2(3) . . . . ?
C14 O15 C16 C17 178.1(2) . . . . ?
C16 O15 C14 C13 1.8(3) . . . . ?
C16 O15 C14 C25 -178.8(2) . . . . ?
C16 C11 C12 O12 -178.0(2) . . . . ?
C16 C11 C12 C13 1.4(3) . . . . ?
C17 S1 C2 N3 1.0(2) . . . . ?
C17 S1 C2 N18 -177.7(2) . . . . ?
C17 C4 C5 C6 175.8(2) . . . . ?
C17 C4 C5 C10 -4.5(4) . . . . ?
C19 N18 C2 S1 0.5(4) . . . . ?
C19 N18 C2 N3 -178.2(2) . . . . ?
C24 O8 C8 C7 2.1(4) . . . . ?
C24 O8 C8 C9 -178.3(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.591
_oxdiff_exptl_absorpt_empirical_full_min 0.604
_oxdiff_exptl_absorpt_spherical_max 0.869
_oxdiff_exptl_absorpt_spherical_min 0.869
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
_oxdiff_twin_reflns_isolated
_oxdiff_twin_reflns_overlapped
_twin_individual_twin_lattice_type
_twin_individual_twin_matrix_11
_twin_individual_twin_matrix_12
_twin_individual_twin_matrix_13
_twin_individual_twin_matrix_21
_twin_individual_twin_matrix_22
_twin_individual_twin_matrix_23
_twin_individual_twin_matrix_31
_twin_individual_twin_matrix_32
_twin_individual_twin_matrix_33
1 0.4532(14) 8395 9492 ref 1.0000 0.0000 0.0000 0.0000 1.0000 0.0000 0.0000
0.0000 1.0000
2 0.5468(14) 7758 9492 nmt 0.9996 0.0056 0.2482 0.0121 -1.0003 0.0019 -0.0014
-0.0001 -0.9999

_twin_special_details            
;
Component 2 rotated by -179.9773° 
around [1.00 0.01 -0.00] (reciprocal) or [0.99 0.00 0.12] (direct)
;
####################################################################### 
# 
# 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_am-161
_database_code_depnum_ccdc_archive 'CCDC 2406499'
loop_
_audit_author_name
_audit_author_address
'Roman Alekseevich Dolotov'
;N D Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2024-11-29 deposited with the CCDC.	2025-03-24 downloaded from the CCDC.
;
_audit_creation_date             2024-10-25
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H18 Cl N4 O S, I, 2(H2 O)'
_chemical_formula_sum            'C22 H22 Cl I N4 O3 S'
_chemical_formula_weight         584.84
_chemical_melting_point          ?
_chemical_oxdiff_formula         C22H18ClN4OSI
_chemical_oxdiff_usercomment     AM-161
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'
I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.18997(5)
_cell_length_b                   8.95782(5)
_cell_length_c                   17.13924(9)
_cell_angle_alpha                97.8836(4)
_cell_angle_beta                 99.1687(5)
_cell_angle_gamma                97.7247(5)
_cell_volume                     1213.809(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    22999
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      79.6090
_cell_measurement_theta_min      5.0260
_shelx_estimated_absorpt_T_max   0.780
_shelx_estimated_absorpt_T_min   0.592
_exptl_absorpt_coefficient_mu    12.441
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64767
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.141a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.600
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.047
_exptl_crystal_size_mid          0.044
_exptl_crystal_size_min          0.021
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_av_unetI/netI     0.0214
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            32044
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.264
_diffrn_reflns_theta_min         2.646
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -26.00  41.00   0.50    0.32    --  -41.40  19.00 -43.00  134
  2  ω    -21.00 123.00   0.50    0.32    --   41.40  19.00 -43.00  288
  3  ω    -21.00 123.00   0.50    0.32    --   41.40  19.00 -43.00  288
  4  ω    -43.00  27.00   0.50    0.32    --   41.40 -19.00 148.00  140
  5  ω   -177.00 -40.00   0.50    0.32    -- -100.00 -19.00 148.00  274
  6  ω   -177.00 -40.00   0.50    0.32    -- -100.00 -19.00 148.00  274
  7  ω     59.00 178.00   0.50    0.32    --  121.50  19.00 -43.00  238
  8  ω     -1.00  44.00   0.50    0.80    --    0.00 -99.00  90.00   90
  9  ω    -26.00  83.00   0.50    0.80    --    0.00  19.00 -43.00  218
 10  ω   -126.00  19.00   0.50    0.32    --  -41.40 -19.00 148.00  290
 11  ω    -43.00  27.00   0.50    0.32    --   41.40 -19.00   0.00  140
 12  ω     34.00  99.00   0.50    0.32    --   41.40-125.00-150.00  130
 13  ω     -1.00  86.00   0.50    0.32    --   41.40 -99.00  30.00  174
 14  ω     -1.00  86.00   0.50    0.32    --   41.40 -99.00 150.00  174
 15  ω     -1.00  86.00   0.50    0.32    --   41.40 -99.00  30.00  174
 16  ω     34.00  99.00   0.50    0.32    --   41.40-125.00  30.00  130
 17  ω     -1.00  28.00   0.50    0.32    --   41.40  97.00 -38.04   58
 18  ω    -71.00 -24.00   0.50    0.32    -- -100.00  61.00-180.00   94
 19  ω    -82.00 -23.00   0.50    0.32    -- -100.00 111.00  30.00  118
 20  ω    -51.00 -21.00   0.50    0.32    -- -100.00  45.00 150.00   60
 21  ω    -51.00 -21.00   0.50    0.32    -- -100.00  45.00 120.00   60
 22  ω   -105.00 -24.00   0.50    0.32    -- -100.00  77.00 -30.00  162
 23  ω   -105.00 -24.00   0.50    0.32    -- -100.00  77.00 -30.00  162
 24  ω     61.00 151.00   0.50    0.32    --  121.50-178.00  60.00  180
 25  ω     61.00 151.00   0.50    0.32    --  121.50-178.00  60.00  180
 26  ω     45.00 108.00   0.50    0.32    --  121.50-111.00 120.00  126
 27  ω     45.00 108.00   0.50    0.32    --  121.50-111.00  60.00  126
 28  ω     92.00 178.00   0.50    0.32    --  121.50  45.00 120.00  172
 29  ω     41.00 106.00   0.50    0.32    --  121.50 -95.00   0.00  130
 30  ω     45.00 108.00   0.50    0.32    --  121.50-111.00-120.00  126
 31  ω     92.00 178.00   0.50    0.32    --  121.50  61.00 120.00  172
 32  ω     61.00 151.00   0.50    0.32    --  121.50-178.00  90.00  180
 33  ω     45.00 108.00   0.50    0.32    --  121.50-111.00-150.00  126
 34  ω     92.00 178.00   0.50    0.32    --  121.50  61.00-120.00  172
 35  ω     41.00 106.00   0.50    0.32    --  121.50 -95.00  90.00  130
 36  ω     41.00 106.00   0.50    0.32    --  121.50 -95.00 -30.00  130
 37  ω    103.00 178.00   0.50    0.32    --  121.50 111.00   0.00  150
 38  ω     87.00 178.00   0.50    0.32    --  121.50  77.00-180.00  182
 39  ω     92.00 178.00   0.50    0.32    --  121.50  61.00-150.00  172
 40  ω     92.00 178.00   0.50    0.32    --  121.50  61.00-150.00  172
 41  ω     45.00 108.00   0.50    0.32    --  121.50-111.00-180.00  126
 42  ω     92.00 178.00   0.50    0.32    --  121.50  45.00-180.00  172
 43  ω     63.00 146.00   0.50    0.32    --  121.50 178.00  30.00  166
 44  ω     92.00 178.00   0.50    0.32    --  121.50  45.00  30.00  172
 45  ω     45.00 108.00   0.50    0.32    --  121.50-111.00   0.00  126
 46  ω     45.00 108.00   0.50    0.32    --  121.50-111.00 -60.00  126
 47  ω     47.00 105.00   0.50    0.32    --  121.50 -77.00  90.00  116
 48  ω     45.00 108.00   0.50    0.32    --  121.50-111.00  90.00  126
 49  ω     45.00 108.00   0.50    0.32    --  121.50-111.00  90.00  126
 50  ω     47.00 105.00   0.50    0.32    --  121.50 -77.00  30.00  116
 51  ω     42.00 178.00   0.50    0.32    --  121.50  15.00  60.00  272
 52  ω     41.00 106.00   0.50    0.32    --  121.50 -95.00 -60.00  130
 53  ω     92.00 178.00   0.50    0.32    --  121.50  45.00 120.00  172
 54  ω     84.00 178.00   0.50    0.32    --  121.50  30.00-180.00  188
 55  ω     42.00 178.00   0.50    0.32    --  121.50  15.00  60.00  272
 56  ω     47.00 105.00   0.50    0.32    --  121.50 -77.00 -60.00  116
 57  ω     47.00 105.00   0.50    0.32    --  121.50 -77.00   0.00  116
 58  ω     45.00 158.00   0.50    0.32    --  121.50 -81.00 153.57  226
 59  ω     87.00 178.00   0.50    0.32    --  121.50  77.00-120.00  182
 60  ω     51.00  98.00   0.50    0.32    --  121.50 -79.00-174.39   94
 61  ω    129.00 154.00   0.50    0.32    --  121.50 -79.00-174.39   50
 62  ω     76.00 107.00   0.50    0.32    --  121.50-111.00  30.00   62
 63  ω     80.00 106.00   0.50    0.32    --  121.50 -95.00-150.00   52
 64  ω     71.00  97.00   0.50    0.32    --  121.50 -95.00  60.00   52
 65  ω     52.00 103.00   0.50    0.32    --  121.50 -95.00 150.00  102
 66  ω    103.00 137.00   0.50    0.32    --  121.50 111.00-120.00   68
 67  ω    141.00 167.00   0.50    0.32    --  121.50 111.00 -90.00   52
 68  ω     42.00  76.00   0.50    0.32    --  121.50 -95.00  30.00   68
 69  ω    151.00 177.00   0.50    0.32    --  121.50  61.00  90.00   52
 70  ω    128.00 157.00   0.50    0.32    --  121.50 -79.00 132.03   58
 71  ω     49.00  75.00   0.50    0.32    --  121.50 -79.00 132.03   52
 72  ω     96.00 149.00   0.50    0.32    --  121.50-178.00   0.00  106
 73  ω     88.00 166.00   0.50    0.32    --  121.50  30.00   0.00  156
 74  ω     92.00 144.00   0.50    0.32    --  121.50  45.00-120.00  104
 75  ω    132.00 158.00   0.50    0.32    --  121.50 -81.00 153.57   52
 76  ω    119.00 145.00   0.50    0.32    --  121.50 -81.00 107.62   52
 77  ω    130.00 160.00   0.50    0.32    --  121.50 -85.00 -78.72   60
 78  ω    120.00 178.00   0.50    0.32    --  121.50  45.00  90.00  116
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1606401000
_diffrn_orient_matrix_UB_12      -0.0957605000
_diffrn_orient_matrix_UB_13      0.0137594000
_diffrn_orient_matrix_UB_21      0.0990875000
_diffrn_orient_matrix_UB_22      -0.1293924000
_diffrn_orient_matrix_UB_23      0.0184238000
_diffrn_orient_matrix_UB_31      0.0404039000
_diffrn_orient_matrix_UB_32      0.0708631000
_diffrn_orient_matrix_UB_33      0.0893575000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5247
_reflns_number_total             5288
_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       'CrysAlisPro 1.171.43.141a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.136a 64-bit (release 23-08-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.141a (Rigaku OD, 2024)'
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.524
_refine_diff_density_min         -0.705
_refine_diff_density_rms         0.080
_refine_ls_extinction_coef       0.00058(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     320
_refine_ls_number_reflns         5288
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0244
_refine_ls_R_factor_gt           0.0242
_refine_ls_restrained_S_all      1.053
_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)+(0.0321P)²+1.5310P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0625
_refine_ls_wR_factor_ref         0.0627
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 H4B-N4
 0.87 with sigma of 0.02
 H4A-N4
 0.87 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C7(H7), C8(H8), C9(H9), C10(H10), C18(H18), C19(H19), C21(H21),
 C22(H22)
3.b Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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
I1 I 1.28195(2) 0.35296(2) 0.82565(2) 0.01784(6) Uani 1 1 d . . . . .
Cl1 Cl 0.49305(8) 0.77231(8) 0.47297(3) 0.03016(13) Uani 1 1 d . . . . .
S1 S 0.74014(6) 0.64555(6) 0.95704(3) 0.01527(10) Uani 1 1 d . . . . .
O1 O 1.0153(2) 0.5929(2) 0.88786(10) 0.0186(3) Uani 1 1 d . . . . .
H1 H 1.071(5) 0.544(4) 0.878(2) 0.032(10) Uiso 1 1 d . . . . .
N1 N 1.0029(2) 0.7852(2) 0.75278(11) 0.0172(4) Uani 1 1 d . . . . .
N2 N 0.9322(3) 0.5550(2) 0.61217(12) 0.0245(4) Uani 1 1 d . . . . .
N3 N 0.5168(2) 0.7601(2) 0.87467(11) 0.0142(3) Uani 1 1 d . . . . .
N4 N 0.4833(3) 0.7646(2) 1.00836(12) 0.0191(4) Uani 1 1 d D . . . .
H4A H 0.523(4) 0.737(3) 1.0527(13) 0.018(7) Uiso 1 1 d D . . . .
H4B H 0.400(3) 0.811(4) 1.005(2) 0.031(9) Uiso 1 1 d D . . . .
C1 C 0.8810(3) 0.5772(2) 0.82172(13) 0.0154(4) Uani 1 1 d . . . . .
C2 C 0.8181(3) 0.4100(2) 0.78296(14) 0.0182(4) Uani 1 1 d . . . . .
C3 C 0.8274(3) 0.3886(3) 0.70509(15) 0.0224(5) Uani 1 1 d . . . . .
H3 H 0.791818 0.294309 0.669776 0.027 Uiso 1 1 calc R U . . .
C4 C 0.8995(3) 0.5299(3) 0.68193(13) 0.0189(4) Uani 1 1 d . . . . .
C5 C 0.9340(3) 0.6462(2) 0.75142(13) 0.0148(4) Uani 1 1 d . . . . .
C6 C 1.0432(3) 0.8161(3) 0.68040(13) 0.0189(4) Uani 1 1 d . . . . .
C7 C 1.1207(3) 0.9644(3) 0.67620(15) 0.0251(5) Uani 1 1 d . . . . .
H7 H 1.144622 1.041186 0.722340 0.030 Uiso 1 1 calc R U . . .
C8 C 1.1616(3) 0.9973(3) 0.60491(17) 0.0304(6) Uani 1 1 d . . . . .
H8 H 1.214410 1.097087 0.602099 0.037 Uiso 1 1 calc R U . . .
C9 C 1.1261(4) 0.8849(3) 0.53650(16) 0.0308(6) Uani 1 1 d . . . . .
H9 H 1.155303 0.909490 0.487785 0.037 Uiso 1 1 calc R U . . .
C10 C 1.0499(4) 0.7402(3) 0.53874(15) 0.0298(6) Uani 1 1 d . . . . .
H10 H 1.026106 0.665389 0.491772 0.036 Uiso 1 1 calc R U . . .
C11 C 1.0067(3) 0.7024(3) 0.61102(14) 0.0219(5) Uani 1 1 d . . . . .
C12 C 0.7603(3) 0.2957(3) 0.83233(16) 0.0245(5) Uani 1 1 d . . . . .
H12A H 0.844640 0.302885 0.880747 0.037 Uiso 1 1 calc R U . . .
H12B H 0.744263 0.192870 0.801231 0.037 Uiso 1 1 calc R U . . .
H12C H 0.654069 0.316263 0.847464 0.037 Uiso 1 1 calc R U . . .
C13 C 0.7465(3) 0.6505(2) 0.85594(12) 0.0145(4) Uani 1 1 d . . . . .
C14 C 0.5621(3) 0.7300(2) 0.94823(13) 0.0150(4) Uani 1 1 d . . . . .
C15 C 0.3753(3) 0.8410(3) 0.85504(14) 0.0197(4) Uani 1 1 d . . . . .
H15A H 0.400346 0.944475 0.885925 0.030 Uiso 1 1 calc R U . . .
H15B H 0.274380 0.785966 0.868395 0.030 Uiso 1 1 calc R U . . .
H15C H 0.356568 0.846796 0.797689 0.030 Uiso 1 1 calc R U . . .
C16 C 0.6194(3) 0.7131(2) 0.82064(12) 0.0144(4) Uani 1 1 d . . . . .
C17 C 0.5788(3) 0.7311(2) 0.73488(13) 0.0150(4) Uani 1 1 d . . . . .
C18 C 0.6462(3) 0.8637(3) 0.70963(14) 0.0220(5) Uani 1 1 d . . . . .
H18 H 0.711972 0.945173 0.747835 0.026 Uiso 1 1 calc R U . . .
C19 C 0.6178(3) 0.8776(3) 0.62880(15) 0.0249(5) Uani 1 1 d . . . . .
H19 H 0.664545 0.967460 0.611390 0.030 Uiso 1 1 calc R U . . .
C20 C 0.5206(3) 0.7584(3) 0.57456(13) 0.0213(5) Uani 1 1 d . . . . .
C21 C 0.4487(3) 0.6271(3) 0.59798(14) 0.0237(5) Uani 1 1 d . . . . .
H21 H 0.380390 0.547425 0.559580 0.028 Uiso 1 1 calc R U . . .
C22 C 0.4783(3) 0.6135(3) 0.67903(14) 0.0211(4) Uani 1 1 d . . . . .
H22 H 0.429788 0.523980 0.696120 0.025 Uiso 1 1 calc R U . . .
O2 O 0.2257(2) 0.9458(2) 1.02305(11) 0.0203(3) Uani 1 1 d . . . . .
H2A H 0.182(4) 0.973(4) 0.987(2) 0.026(8) Uiso 1 1 d . . . . .
H2B H 0.165(5) 0.942(4) 1.051(2) 0.038(10) Uiso 1 1 d . . . . .
O3 O 0.0383(2) 1.0298(2) 0.88508(10) 0.0203(3) Uani 1 1 d . . . . .
H3A H 0.033(4) 0.968(4) 0.848(2) 0.028(9) Uiso 1 1 d . . . . .
H3B H 0.084(4) 1.098(4) 0.8729(19) 0.021(8) Uiso 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 C20 1.744(2) . ?
S1 C13 1.748(2) . ?
S1 C14 1.726(2) . ?
O1 H1 0.70(4) . ?
O1 C1 1.426(3) . ?
N1 C5 1.291(3) . ?
N1 C6 1.387(3) . ?
N2 C4 1.308(3) . ?
N2 C11 1.382(3) . ?
N3 C14 1.331(3) . ?
N3 C15 1.466(3) . ?
N3 C16 1.406(3) . ?
N4 H4A 0.858(17) . ?
N4 H4B 0.842(18) . ?
N4 C14 1.324(3) . ?
C1 C2 1.537(3) . ?
C1 C5 1.524(3) . ?
C1 C13 1.510(3) . ?
C2 C3 1.338(3) . ?
C2 C12 1.491(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.456(3) . ?
C4 C5 1.434(3) . ?
C6 C7 1.409(3) . ?
C6 C11 1.419(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.377(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.401(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.369(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.413(3) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C16 1.347(3) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.490(3) . ?
C17 C18 1.394(3) . ?
C17 C22 1.394(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.393(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.379(4) . ?
C20 C21 1.381(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.397(3) . ?
C22 H22 0.9500 . ?
O2 H2A 0.76(4) . ?
O2 H2B 0.75(4) . ?
O3 H3A 0.77(4) . ?
O3 H3B 0.74(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
C14 S1 C13 89.98(10) . . ?
C1 O1 H1 109(3) . . ?
C5 N1 C6 114.65(19) . . ?
C4 N2 C11 114.5(2) . . ?
C14 N3 C15 121.28(18) . . ?
C14 N3 C16 114.18(18) . . ?
C16 N3 C15 124.50(18) . . ?
H4A N4 H4B 120(3) . . ?
C14 N4 H4A 115(2) . . ?
C14 N4 H4B 124(2) . . ?
O1 C1 C2 112.61(18) . . ?
O1 C1 C5 112.77(18) . . ?
O1 C1 C13 104.75(17) . . ?
C5 C1 C2 101.39(17) . . ?
C13 C1 C2 112.03(18) . . ?
C13 C1 C5 113.58(18) . . ?
C3 C2 C1 111.2(2) . . ?
C3 C2 C12 128.7(2) . . ?
C12 C2 C1 120.1(2) . . ?
C2 C3 H3 124.7 . . ?
C2 C3 C4 110.6(2) . . ?
C4 C3 H3 124.7 . . ?
N2 C4 C3 129.1(2) . . ?
N2 C4 C5 123.1(2) . . ?
C5 C4 C3 107.8(2) . . ?
N1 C5 C1 126.75(19) . . ?
N1 C5 C4 124.3(2) . . ?
C4 C5 C1 108.97(19) . . ?
N1 C6 C7 118.8(2) . . ?
N1 C6 C11 121.4(2) . . ?
C7 C6 C11 119.8(2) . . ?
C6 C7 H7 120.2 . . ?
C8 C7 C6 119.7(2) . . ?
C8 C7 H7 120.2 . . ?
C7 C8 H8 119.7 . . ?
C7 C8 C9 120.5(3) . . ?
C9 C8 H8 119.7 . . ?
C8 C9 H9 119.5 . . ?
C10 C9 C8 121.0(2) . . ?
C10 C9 H9 119.5 . . ?
C9 C10 H10 120.0 . . ?
C9 C10 C11 119.9(2) . . ?
C11 C10 H10 120.0 . . ?
N2 C11 C6 122.0(2) . . ?
N2 C11 C10 118.9(2) . . ?
C10 C11 C6 119.0(2) . . ?
C2 C12 H12A 109.5 . . ?
C2 C12 H12B 109.5 . . ?
C2 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C1 C13 S1 117.03(15) . . ?
C16 C13 S1 111.81(16) . . ?
C16 C13 C1 131.01(19) . . ?
N3 C14 S1 112.00(16) . . ?
N4 C14 S1 123.77(17) . . ?
N4 C14 N3 124.2(2) . . ?
N3 C15 H15A 109.5 . . ?
N3 C15 H15B 109.5 . . ?
N3 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N3 C16 C17 120.43(18) . . ?
C13 C16 N3 111.99(18) . . ?
C13 C16 C17 127.55(19) . . ?
C18 C17 C16 120.0(2) . . ?
C22 C17 C16 120.3(2) . . ?
C22 C17 C18 119.6(2) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 C17 120.5(2) . . ?
C19 C18 H18 119.7 . . ?
C18 C19 H19 120.7 . . ?
C20 C19 C18 118.7(2) . . ?
C20 C19 H19 120.7 . . ?
C19 C20 Cl1 118.63(19) . . ?
C19 C20 C21 122.1(2) . . ?
C21 C20 Cl1 119.20(19) . . ?
C20 C21 H21 120.5 . . ?
C20 C21 C22 118.9(2) . . ?
C22 C21 H21 120.5 . . ?
C17 C22 C21 120.1(2) . . ?
C17 C22 H22 120.0 . . ?
C21 C22 H22 120.0 . . ?
H2A O2 H2B 106(4) . . ?
H3A O3 H3B 102(3) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 I1 0.70(4) 2.75(4) 3.4496(17) 175(4) . yes
N4 H4A I1 0.858(17) 2.701(19) 3.539(2) 165(3) 2_767 yes
N4 H4B O2 0.842(18) 2.024(19) 2.851(3) 167(3) . yes
O2 H2A O3 0.76(4) 2.10(4) 2.856(3) 174(3) . yes
O2 H2B O3 0.75(4) 2.16(4) 2.884(2) 165(4) 2_577 yes
O3 H3A N1 0.77(4) 2.11(4) 2.879(3) 175(3) 1_455 yes
O3 H3B I1 0.74(4) 2.91(4) 3.6471(19) 176(3) 1_465 yes

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
Cl1 C20 C21 C22 176.79(19) . . . . ?
S1 C13 C16 N3 0.9(2) . . . . ?
S1 C13 C16 C17 -177.23(18) . . . . ?
O1 C1 C2 C3 -122.8(2) . . . . ?
O1 C1 C2 C12 56.2(3) . . . . ?
O1 C1 C5 N1 -56.4(3) . . . . ?
O1 C1 C5 C4 122.0(2) . . . . ?
O1 C1 C13 S1 -29.1(2) . . . . ?
O1 C1 C13 C16 155.7(2) . . . . ?
N1 C6 C7 C8 -180.0(2) . . . . ?
N1 C6 C11 N2 -1.2(4) . . . . ?
N1 C6 C11 C10 179.7(2) . . . . ?
N2 C4 C5 N1 -1.4(4) . . . . ?
N2 C4 C5 C1 -179.8(2) . . . . ?
N3 C16 C17 C18 91.2(3) . . . . ?
N3 C16 C17 C22 -91.1(3) . . . . ?
C1 C2 C3 C4 1.9(3) . . . . ?
C1 C13 C16 N3 176.3(2) . . . . ?
C1 C13 C16 C17 -1.8(4) . . . . ?
C2 C1 C5 N1 -177.0(2) . . . . ?
C2 C1 C5 C4 1.4(2) . . . . ?
C2 C1 C13 S1 93.2(2) . . . . ?
C2 C1 C13 C16 -82.0(3) . . . . ?
C2 C3 C4 N2 178.4(2) . . . . ?
C2 C3 C4 C5 -0.9(3) . . . . ?
C3 C4 C5 N1 178.1(2) . . . . ?
C3 C4 C5 C1 -0.4(2) . . . . ?
C4 N2 C11 C6 -0.3(3) . . . . ?
C4 N2 C11 C10 178.8(2) . . . . ?
C5 N1 C6 C7 -179.3(2) . . . . ?
C5 N1 C6 C11 1.3(3) . . . . ?
C5 C1 C2 C3 -2.0(2) . . . . ?
C5 C1 C2 C12 177.0(2) . . . . ?
C5 C1 C13 S1 -152.61(16) . . . . ?
C5 C1 C13 C16 32.2(3) . . . . ?
C6 N1 C5 C1 178.1(2) . . . . ?
C6 N1 C5 C4 -0.1(3) . . . . ?
C6 C7 C8 C9 0.3(4) . . . . ?
C7 C6 C11 N2 179.4(2) . . . . ?
C7 C6 C11 C10 0.3(4) . . . . ?
C7 C8 C9 C10 0.1(4) . . . . ?
C8 C9 C10 C11 -0.3(4) . . . . ?
C9 C10 C11 N2 -179.0(2) . . . . ?
C9 C10 C11 C6 0.1(4) . . . . ?
C11 N2 C4 C3 -177.8(2) . . . . ?
C11 N2 C4 C5 1.5(3) . . . . ?
C11 C6 C7 C8 -0.5(4) . . . . ?
C12 C2 C3 C4 -176.9(2) . . . . ?
C13 S1 C14 N3 -1.03(17) . . . . ?
C13 S1 C14 N4 -179.1(2) . . . . ?
C13 C1 C2 C3 119.4(2) . . . . ?
C13 C1 C2 C12 -61.6(3) . . . . ?
C13 C1 C5 N1 62.6(3) . . . . ?
C13 C1 C5 C4 -119.0(2) . . . . ?
C13 C16 C17 C18 -90.8(3) . . . . ?
C13 C16 C17 C22 86.9(3) . . . . ?
C14 S1 C13 C1 -176.08(17) . . . . ?
C14 S1 C13 C16 0.03(18) . . . . ?
C14 N3 C16 C13 -1.8(3) . . . . ?
C14 N3 C16 C17 176.53(19) . . . . ?
C15 N3 C14 S1 -175.92(16) . . . . ?
C15 N3 C14 N4 2.2(3) . . . . ?
C15 N3 C16 C13 175.8(2) . . . . ?
C15 N3 C16 C17 -5.8(3) . . . . ?
C16 N3 C14 S1 1.8(2) . . . . ?
C16 N3 C14 N4 179.9(2) . . . . ?
C16 C17 C18 C19 175.9(2) . . . . ?
C16 C17 C22 C21 -176.2(2) . . . . ?
C17 C18 C19 C20 0.6(4) . . . . ?
C18 C17 C22 C21 1.6(4) . . . . ?
C18 C19 C20 Cl1 -177.10(19) . . . . ?
C18 C19 C20 C21 1.0(4) . . . . ?
C19 C20 C21 C22 -1.3(4) . . . . ?
C20 C21 C22 C17 0.0(4) . . . . ?
C22 C17 C18 C19 -1.9(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.446
_oxdiff_exptl_absorpt_empirical_full_min 0.802
####################################################################### 
# 
# 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_am-117
_database_code_depnum_ccdc_archive 'CCDC 2406495'
loop_
_audit_author_name
_audit_author_address
'Darina Ildarovna Nasyrova'
;N D Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2024-11-29 deposited with the CCDC.	2025-03-24 downloaded from the CCDC.
;
_audit_creation_date             2024-10-25
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.11.18 svn.ra9532c28 for OlexSys, GUI svn.r6429)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H20 Cl N3 O4 S'
_chemical_formula_sum            'C22 H20 Cl N3 O4 S'
_chemical_formula_weight         457.92
_chemical_melting_point          ?
_chemical_oxdiff_formula         C22H16ClN4OSI
_chemical_oxdiff_usercomment     AM-117
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'
S S 0.3331 0.5567 '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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   33.1807(2)
_cell_length_b                   10.98210(10)
_cell_length_c                   13.83250(10)
_cell_angle_alpha                90
_cell_angle_beta                 92.2370(10)
_cell_angle_gamma                90
_cell_volume                     5036.64(7)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    42503
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      79.9920
_cell_measurement_theta_min      2.6620
_shelx_estimated_absorpt_T_max   0.732
_shelx_estimated_absorpt_T_min   0.611
_exptl_absorpt_coefficient_mu    2.372
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.520
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.136a (Rigaku Oxford Diffraction, 2024)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.208
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1904
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-21 1 0 0.1115
21 -2 0 0.0404
3 7 -2 0.1198
-16 0 -6 0.0785
0 -7 -3 0.0968
16 -3 4 0.0637
16 1 6 0.0807
0 7 3 0.0726
-5 -1 -8 0.1003
-7 6 4 0.0701
4 2 8 0.0818
10 -2 -8 0.0823
1 2 -9 0.1090
8 -5 5 0.0714
-8 1 8 0.0731
19 0 -5 0.0452
-18 -1 5 0.0820

_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.14
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-21.2300 1.1799 0.1642 -0.1657 -0.7026 -0.6920
20.8830 -1.7135 0.0010 0.1524 0.6476 0.7466
2.6442 6.8864 -2.0870 0.1555 0.6410 -0.7516
-16.1430 -0.1218 -5.6689 0.5204 -0.6740 -0.5244
0.0669 -6.6606 -3.2100 0.4373 -0.5721 0.6938
15.9902 -3.4511 3.8814 -0.2798 0.3593 0.8903
15.6549 0.7878 5.8225 -0.5488 0.7114 0.4390
0.0875 6.6456 3.2563 -0.4412 0.5772 -0.6871
-5.1020 -1.2362 -8.4936 0.9124 -0.3762 -0.1614
-7.1639 5.8298 4.3380 -0.5942 0.2478 -0.7652
3.6448 1.9802 8.4262 -0.9237 0.3813 0.0372
9.9272 -1.9508 -7.7394 0.9330 0.1395 0.3319
1.3050 2.1288 -8.5647 0.9166 0.1391 -0.3748
8.1337 -5.1833 5.0024 -0.4289 -0.0672 0.9008
-8.1862 0.9897 8.3406 -0.9754 -0.1464 -0.1651
18.8473 0.1786 -4.6455 0.6230 0.6798 0.3871
-17.8239 -1.1513 5.1164 -0.6555 -0.7159 -0.2405

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_av_unetI/netI     0.0135
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       42
_diffrn_reflns_limit_h_min       -41
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            64615
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.310
_diffrn_reflns_theta_min         2.665
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -32.00  80.00   0.40    0.30    --    0.00  48.00 173.00  280
  2  ω    -32.00  80.00   0.40    0.30    --    0.00  48.00 173.00  280
  3  ω    -54.00  18.00   0.40    3.00    --  -61.62  48.00 173.00  180
  4  ω     30.00 140.00   0.40    3.00    --   61.62  48.00 173.00  275
  5  ω    -18.00  54.00   0.40    3.00    --   61.62 -48.00  24.00  180
  6  ω    -54.00 -22.00   0.40    6.00    -- -101.75  48.00 173.00   80
  7  ω   -177.00 -71.00   0.40    6.00    -- -101.75 -48.00  24.00  265
  8  ω     91.00 177.00   0.40    6.00    --  123.25  48.00 173.00  215
  9  ω     91.00 177.00   0.40    6.00    --  123.25  48.00 173.00  215
 10  ω     -1.00  45.00   0.40    0.30    --    0.00 -99.00  30.00  115
 11  ω    -79.00  31.00   0.40    0.30    --    0.00 -48.00  24.00  275
 12  ω   -143.00 -87.00   0.40    3.00    --  -61.62 -99.00 150.00  140
 13  ω   -141.00 -31.00   0.40    3.00    --  -61.62 -48.00  24.00  275
 14  ω   -143.00 -87.00   0.40    3.00    --  -61.62 -99.00-180.00  140
 15  ω     33.00 137.00   0.40    3.00    --   61.62  57.00 -60.00  260
 16  ω     25.00 137.00   0.40    3.00    --   61.62  77.00-120.00  280
 17  ω     33.00 137.00   0.40    3.00    --   61.62  57.00-120.00  260
 18  ω     25.00 137.00   0.40    3.00    --   61.62  77.00-120.00  280
 19  ω   -177.00 -69.00   0.40    6.00    -- -101.75 -71.00-108.10  270
 20  ω   -177.00 -65.00   0.40    6.00    -- -101.75 -77.00 -60.00  280
 21  ω   -177.00 -71.00   0.40    6.00    -- -101.75 -51.00 -58.65  265
 22  ω   -177.00 -65.00   0.40    6.00    -- -101.75 -77.00 -90.00  280
 23  ω   -177.00 -67.00   0.40    6.00    -- -101.75 -73.00 -73.65  275
 24  ω   -177.00 -71.00   0.40    6.00    -- -101.75 -60.00-139.17  265
 25  ω   -177.00 -69.00   0.40    6.00    -- -101.75 -71.00-108.10  270
 26  ω    -71.00 -27.00   0.40    6.00    -- -101.75  61.00 -60.00  110
 27  ω    -51.00 -21.00   0.40    6.00    -- -101.75  45.00   0.00   75
 28  ω    -51.00 -21.00   0.40    6.00    -- -101.75  45.00 -60.00   75
 29  ω   -177.00 -65.00   0.40    6.00    -- -101.75 -77.00 -90.00  280
 30  ω    -51.00 -21.00   0.40    6.00    -- -101.75  45.00 150.00   75
 31  ω   -177.00 -69.00   0.40    6.00    -- -101.75 -68.00 -96.56  270
 32  ω   -177.00 -71.00   0.40    6.00    -- -101.75 -51.00 -58.65  265
 33  ω     91.00 177.00   0.40    6.00    --  123.25  45.00 -60.00  215
 34  ω     87.00 177.00   0.40    6.00    --  123.25  77.00 -30.00  225
 35  ω     91.00 177.00   0.40    6.00    --  123.25  45.00 -60.00  215
 36  ω     79.00 177.00   0.40    6.00    --  123.25  30.00-120.00  245
 37  ω     63.00 145.00   0.40    6.00    --  123.25 178.00  90.00  205
 38  ω     87.00 177.00   0.40    6.00    --  123.25  77.00 -90.00  225
 39  ω     87.00 177.00   0.40    6.00    --  123.25  77.00 -90.00  225
 40  ω    151.00 176.20   0.40    6.00    --  123.25 111.00  60.00   63
 41  ω    152.80 178.00   0.40    6.00    --  123.25   0.00  30.00   63
 42  ω    111.00 147.00   0.40    6.00    --  123.25 111.00  60.00   90
 43  ω     36.00  70.00   0.40    6.00    --  123.25   0.00  30.00   85
 44  ω     94.00 146.00   0.40    6.00    --  123.25  61.00 -30.00  130
 45  ω    135.00 163.00   0.40    6.00    --  123.25  77.00  60.00   70
 46  ω     99.00 174.20   0.40    6.00    --  123.25  61.00-120.00  188
 47  ω     73.00  99.00   0.40    6.00    --  123.25 -77.00 -30.00   65
 48  ω     41.00  92.20   0.40    6.00    --  123.25 -95.00 120.00  128
 49  ω    108.00 133.20   0.40    6.00    --  123.25  45.00 -30.00   63
 50  ω     62.00 111.20   0.40    6.00    --  123.25-178.00 -90.00  123
 51  ω    124.00 161.20   0.40    6.00    --  123.25 -81.00  98.31   93
 52  ω    117.00 161.00   0.40    6.00    --  123.25 -80.00 -24.05  110
 53  ω     96.00 173.20   0.40    6.00    --  123.25  61.00 -90.00  193
 54  ω    105.00 131.00   0.40    6.00    --  123.25  30.00 -60.00   65
 55  ω     87.00 113.00   0.40    6.00    --  123.25  77.00  60.00   65
 56  ω    106.00 151.20   0.40    6.00    --  123.25  45.00-120.00  113
 57  ω     93.00 126.20   0.40    6.00    --  123.25  61.00  60.00   83
 58  ω    137.00 165.00   0.40    6.00    --  123.25  45.00  30.00   70
 59  ω     89.00 116.20   0.40    6.00    --  123.25   0.00  30.00   68
 60  ω    105.00 131.00   0.40    6.00    --  123.25  45.00  30.00   65
 61  ω     71.00 101.00   0.40    6.00    --  123.25 178.00   0.00   75
 62  ω    102.00 136.00   0.40    6.00    --  123.25  61.00  30.00   85
 63  ω    100.00 126.00   0.40    6.00    --  123.25 178.00 -60.00   65
 64  ω     45.00  92.20   0.40    6.00    --  123.25 -80.00  84.53  118
 65  ω    107.00 153.00   0.40    6.00    --  123.25 -80.00  84.53  115
 66  ω     87.00 177.00   0.40    6.00    --  123.25  77.00 -60.00  225
 67  ω     45.00  70.20   0.40    6.00    --  123.25-111.00 -30.00   63
 68  ω    133.00 169.00   0.40    6.00    --  123.25 111.00-120.00   90
 69  ω    117.00 152.20   0.40    6.00    --  123.25 111.00 -90.00   88
 70  ω     64.00  97.20   0.40    6.00    --  123.25 178.00  60.00   83
 71  ω    118.00 159.20   0.40    6.00    --  123.25  61.00-150.00  103
 72  ω     87.00 112.20   0.40    6.00    --  123.25  77.00-120.00   63
 73  ω     60.00  86.00   0.40    6.00    --  123.25 -77.00 -90.00   65
 74  ω    125.00 156.20   0.40    6.00    --  123.25 -81.00  42.01   78
 75  ω    125.00 151.00   0.40    6.00    --  123.25 111.00  30.00   65
 76  ω     45.00  76.20   0.40    6.00    --  123.25 -81.00  42.01   78
 77  ω    111.80 161.00   0.40    6.00    --  123.25 -80.00 127.57  123
 78  ω    128.00 175.20   0.40    6.00    --  123.25  77.00-150.00  118
 79  ω     49.00  84.20   0.40    6.00    --  123.25-111.00 -60.00   88
 80  ω     63.00  89.00   0.40    6.00    --  123.25 -80.00 127.57   65
 81  ω     71.00  97.00   0.40    6.00    --  123.25-111.00 -30.00   65
 82  ω     42.00 104.00   0.40    6.00    --  123.25 -95.00 -30.00  155
 83  ω     41.00 105.00   0.40    6.00    --  123.25 -95.00  30.00  160
 84  ω     47.00  73.00   0.40    6.00    --  123.25 -95.00 150.00   65
 85  ω    104.00 147.20   0.40    6.00    --  123.25 111.00-180.00  108
 86  ω     93.00 142.20   0.40    6.00    --  123.25 178.00 150.00  123
 87  ω     96.00 126.00   0.40    6.00    --  123.25  61.00 -60.00   75
 88  ω    107.00 151.00   0.40    6.00    --  123.25-178.00-120.00  110
 89  ω     92.00 117.20   0.40    6.00    --  123.25  77.00-150.00   63
 90  ω    143.00 177.00   0.40    6.00    --  123.25  45.00  90.00   85
 91  ω     66.00  98.00   0.40    6.00    --  123.25  24.00 -45.12   80
 92  ω     49.00  94.20   0.40    6.00    --  123.25-111.00  30.00  113
 93  ω     71.80 105.00   0.40    6.00    --  123.25 -95.00  90.00   83
 94  ω     71.00  97.00   0.40    6.00    --  123.25  -2.00  19.80   65
 95  ω    152.00 177.20   0.40    6.00    --  123.25  30.00-120.00   63
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0062394000
_diffrn_orient_matrix_UB_12      -0.0129304000
_diffrn_orient_matrix_UB_13      -0.1092831000
_diffrn_orient_matrix_UB_21      0.0377027000
_diffrn_orient_matrix_UB_22      0.0815651000
_diffrn_orient_matrix_UB_23      0.0097749000
_diffrn_orient_matrix_UB_31      0.0264492000
_diffrn_orient_matrix_UB_32      -0.1133583000
_diffrn_orient_matrix_UB_33      0.0196190000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5313
_reflns_number_total             5469
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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       'CrysAlisPro 1.171.43.136a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.136a 64-bit (release 23-08-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.136a (Rigaku OD, 2024)'
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.394
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     294
_refine_ls_number_reflns         5469
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0419
_refine_ls_restrained_S_all      1.048
_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)+(0.0448P)²+9.6079P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1087
_refine_ls_wR_factor_ref         0.1092
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C15-C16A \\sim C15-C16B
 with sigma of 0.003
3. Uiso/Uaniso restraints and constraints
Uanis(C16A) = Uanis(C16B)
4. Others
 Sof(C16B)=Sof(H16D)=Sof(H16E)=Sof(H16F)=1-FVAR(1)
 Sof(C16A)=Sof(H16A)=Sof(H16B)=Sof(H16C)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7), C11(H11)
5.b Idealised Me refined as rotating group:
 C16A(H16A,H16B,H16C), C16B(H16D,H16E,H16F), C19(H19A,H19B,H19C), C20(H20A,
 H20B,H20C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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 0.50197(2) 0.79475(4) 0.61962(3) 0.03608(11) Uani 1 1 d . . . . .
S1 S 0.43957(2) 0.05478(4) 0.60636(3) 0.02759(10) Uani 1 1 d . . . . .
O1 O 0.52858(3) 0.10570(12) 0.63700(9) 0.0286(3) Uani 1 1 d . . . . .
O2 O 0.58513(4) 0.43428(13) 0.66208(11) 0.0375(3) Uani 1 1 d . . . . .
O3 O 0.32425(4) 0.17873(17) 0.73352(13) 0.0509(4) Uani 1 1 d . . . . .
O4 O 0.38352(4) -0.10450(13) 0.58868(11) 0.0399(3) Uani 1 1 d . . . . .
N1 N 0.39832(4) 0.25731(14) 0.58987(11) 0.0282(3) Uani 1 1 d . . . . .
N2 N 0.35748(4) 0.08275(15) 0.57566(12) 0.0319(3) Uani 1 1 d . . . . .
N3 N 0.32438(4) 0.16124(16) 0.56986(14) 0.0370(4) Uani 1 1 d . . . . .
C1 C 0.39522(5) 0.13910(17) 0.59044(13) 0.0283(3) Uani 1 1 d . . . . .
C2 C 0.43863(5) 0.28918(17) 0.60447(12) 0.0264(3) Uani 1 1 d . . . . .
C3 C 0.45325(5) 0.41153(17) 0.60863(12) 0.0267(3) Uani 1 1 d . . . . .
C4 C 0.42721(5) 0.51231(18) 0.59738(13) 0.0307(4) Uani 1 1 d . . . . .
H4 H 0.399077 0.498860 0.587362 0.037 Uiso 1 1 calc R U . . .
C5 C 0.44156(6) 0.62919(18) 0.60057(13) 0.0319(4) Uani 1 1 d . . . . .
H5 H 0.423837 0.696664 0.592401 0.038 Uiso 1 1 calc R U . . .
C6 C 0.48306(6) 0.64634(17) 0.61621(13) 0.0304(4) Uani 1 1 d . . . . .
C7 C 0.50974(5) 0.55160(17) 0.62802(12) 0.0287(4) Uani 1 1 d . . . . .
H7 H 0.537719 0.567504 0.638450 0.034 Uiso 1 1 calc R U . . .
C8 C 0.49554(5) 0.43022(16) 0.62462(12) 0.0261(3) Uani 1 1 d . . . . .
C9 C 0.52273(5) 0.32680(17) 0.63538(12) 0.0262(3) Uani 1 1 d . . . . .
C10 C 0.56680(5) 0.33657(17) 0.65308(13) 0.0293(4) Uani 1 1 d . . . . .
C11 C 0.58805(5) 0.22203(18) 0.65984(13) 0.0318(4) Uani 1 1 d . . . . .
H11 H 0.616508 0.223505 0.670354 0.038 Uiso 1 1 calc R U . . .
C12 C 0.56969(5) 0.11414(18) 0.65204(13) 0.0298(4) Uani 1 1 d . . . . .
C13 C 0.50675(5) 0.21091(16) 0.62960(12) 0.0264(3) Uani 1 1 d . . . . .
C14 C 0.46482(5) 0.19241(16) 0.61490(12) 0.0268(3) Uani 1 1 d . . . . .
C15 C 0.31298(6) 0.2145(2) 0.6541(2) 0.0472(5) Uani 1 1 d D . . . .
C16A C 0.27987(19) 0.3043(6) 0.6222(6) 0.0543(12) Uani 0.514(9) 1 d D . P A 1
H16A H 0.278566 0.310000 0.551425 0.081 Uiso 0.514(9) 1 calc R U P A 1
H16B H 0.285952 0.384622 0.649900 0.081 Uiso 0.514(9) 1 calc R U P A 1
H16C H 0.253879 0.275757 0.644740 0.081 Uiso 0.514(9) 1 calc R U P A 1
C16B C 0.2883(2) 0.3319(5) 0.6537(7) 0.0543(12) Uani 0.486(9) 1 d D . P A 2
H16D H 0.259682 0.312116 0.659846 0.081 Uiso 0.486(9) 1 calc R U P A 2
H16E H 0.291857 0.375638 0.592900 0.081 Uiso 0.486(9) 1 calc R U P A 2
H16F H 0.297420 0.383321 0.708182 0.081 Uiso 0.486(9) 1 calc R U P A 2
C17 C 0.35331(5) -0.04363(18) 0.57334(14) 0.0340(4) Uani 1 1 d . . . . .
C18 C 0.31216(6) -0.1024(2) 0.54917(16) 0.0388(4) Uani 1 1 d . . . . .
C19 C 0.31988(7) -0.2397(2) 0.53931(19) 0.0490(5) Uani 1 1 d . . . . .
H19A H 0.338760 -0.253823 0.487742 0.073 Uiso 1 1 calc R U . . .
H19B H 0.294366 -0.281426 0.523358 0.073 Uiso 1 1 calc R U . . .
H19C H 0.331421 -0.271462 0.600542 0.073 Uiso 1 1 calc R U . . .
C20 C 0.28334(7) -0.0816(2) 0.63157(19) 0.0524(6) Uani 1 1 d . . . . .
H20A H 0.297147 -0.101221 0.693534 0.079 Uiso 1 1 calc R U . . .
H20B H 0.259628 -0.134096 0.622079 0.079 Uiso 1 1 calc R U . . .
H20C H 0.274810 0.003837 0.631768 0.079 Uiso 1 1 calc R U . . .
C21 C 0.29400(7) -0.0559(2) 0.45217(18) 0.0503(6) Uani 1 1 d . . . . .
H21A H 0.288236 0.031301 0.457231 0.075 Uiso 1 1 calc R U . . .
H21B H 0.268944 -0.100055 0.436163 0.075 Uiso 1 1 calc R U . . .
H21C H 0.313229 -0.069416 0.401242 0.075 Uiso 1 1 calc R U . . .
C22 C 0.58893(5) -0.00770(19) 0.65807(15) 0.0349(4) Uani 1 1 d . . . . .
H22A H 0.575354 -0.057519 0.705756 0.052 Uiso 1 1 calc R U . . .
H22B H 0.617459 0.001326 0.677807 0.052 Uiso 1 1 calc R U . . .
H22C H 0.586680 -0.047401 0.594640 0.052 Uiso 1 1 calc R U . . .
H3 H 0.3210(9) 0.202(3) 0.506(2) 0.069(9) Uiso 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 C6 1.7465(19) . ?
S1 C1 1.7454(18) . ?
S1 C14 1.7298(18) . ?
O1 C12 1.375(2) . ?
O1 C13 1.365(2) . ?
O2 C10 1.237(2) . ?
O3 C15 1.212(3) . ?
O4 C17 1.217(2) . ?
N1 C1 1.302(2) . ?
N1 C2 1.390(2) . ?
N2 N3 1.396(2) . ?
N2 C1 1.405(2) . ?
N2 C17 1.395(3) . ?
N3 C15 1.370(3) . ?
N3 H3 0.99(3) . ?
C2 C3 1.429(2) . ?
C2 C14 1.377(2) . ?
C3 C4 1.409(3) . ?
C3 C8 1.427(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.369(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.398(3) . ?
C6 C7 1.372(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.414(2) . ?
C8 C9 1.455(2) . ?
C9 C10 1.477(2) . ?
C9 C13 1.380(3) . ?
C10 C11 1.443(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.335(3) . ?
C12 C22 1.484(3) . ?
C13 C14 1.413(2) . ?
C15 C16A 1.529(4) . ?
C15 C16B 1.529(4) . ?
C16A H16A 0.9800 . ?
C16A H16B 0.9800 . ?
C16A H16C 0.9800 . ?
C16B H16D 0.9800 . ?
C16B H16E 0.9800 . ?
C16B H16F 0.9800 . ?
C17 C18 1.535(2) . ?
C18 C19 1.536(3) . ?
C18 C20 1.533(3) . ?
C18 C21 1.537(3) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 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
C14 S1 C1 87.06(8) . . ?
C13 O1 C12 118.32(14) . . ?
C1 N1 C2 109.02(15) . . ?
N3 N2 C1 115.55(15) . . ?
C17 N2 N3 122.40(15) . . ?
C17 N2 C1 121.92(15) . . ?
N2 N3 H3 113.0(18) . . ?
C15 N3 N2 117.20(17) . . ?
C15 N3 H3 122.5(18) . . ?
N1 C1 S1 117.60(13) . . ?
N1 C1 N2 120.56(16) . . ?
N2 C1 S1 121.81(14) . . ?
N1 C2 C3 124.47(16) . . ?
C14 C2 N1 114.88(16) . . ?
C14 C2 C3 120.64(15) . . ?
C4 C3 C2 121.90(16) . . ?
C4 C3 C8 119.95(16) . . ?
C8 C3 C2 118.15(16) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 C3 121.46(17) . . ?
C5 C4 H4 119.3 . . ?
C4 C5 H5 121.0 . . ?
C4 C5 C6 118.05(17) . . ?
C6 C5 H5 121.0 . . ?
C5 C6 Cl1 118.71(15) . . ?
C7 C6 Cl1 118.37(14) . . ?
C7 C6 C5 122.91(17) . . ?
C6 C7 H7 120.1 . . ?
C6 C7 C8 119.89(16) . . ?
C8 C7 H7 120.1 . . ?
C3 C8 C9 120.39(16) . . ?
C7 C8 C3 117.73(16) . . ?
C7 C8 C9 121.87(15) . . ?
C8 C9 C10 124.49(16) . . ?
C13 C9 C8 118.62(15) . . ?
C13 C9 C10 116.88(16) . . ?
O2 C10 C9 124.01(17) . . ?
O2 C10 C11 120.81(16) . . ?
C11 C10 C9 115.18(16) . . ?
C10 C11 H11 118.4 . . ?
C12 C11 C10 123.24(16) . . ?
C12 C11 H11 118.4 . . ?
O1 C12 C22 111.71(16) . . ?
C11 C12 O1 121.27(17) . . ?
C11 C12 C22 127.02(16) . . ?
O1 C13 C9 125.09(15) . . ?
O1 C13 C14 113.93(15) . . ?
C9 C13 C14 120.98(16) . . ?
C2 C14 S1 111.43(13) . . ?
C2 C14 C13 121.20(16) . . ?
C13 C14 S1 127.36(14) . . ?
O3 C15 N3 123.2(2) . . ?
O3 C15 C16A 131.6(4) . . ?
O3 C15 C16B 115.0(4) . . ?
N3 C15 C16A 104.4(4) . . ?
N3 C15 C16B 121.5(4) . . ?
C15 C16A H16A 109.5 . . ?
C15 C16A H16B 109.5 . . ?
C15 C16A H16C 109.5 . . ?
H16A C16A H16B 109.5 . . ?
H16A C16A H16C 109.5 . . ?
H16B C16A H16C 109.5 . . ?
C15 C16B H16D 109.5 . . ?
C15 C16B H16E 109.5 . . ?
C15 C16B H16F 109.5 . . ?
H16D C16B H16E 109.5 . . ?
H16D C16B H16F 109.5 . . ?
H16E C16B H16F 109.5 . . ?
O4 C17 N2 117.54(17) . . ?
O4 C17 C18 121.77(18) . . ?
N2 C17 C18 120.66(17) . . ?
C17 C18 C19 106.39(17) . . ?
C17 C18 C21 111.44(17) . . ?
C19 C18 C21 108.03(19) . . ?
C20 C18 C17 110.52(18) . . ?
C20 C18 C19 108.86(19) . . ?
C20 C18 C21 111.40(19) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C12 C22 H22A 109.5 . . ?
C12 C22 H22B 109.5 . . ?
C12 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
Cl1 C6 C7 C8 -179.32(13) . . . . ?
O1 C13 C14 S1 0.3(2) . . . . ?
O1 C13 C14 C2 -179.00(15) . . . . ?
O2 C10 C11 C12 179.04(18) . . . . ?
O4 C17 C18 C19 -5.8(3) . . . . ?
O4 C17 C18 C20 112.2(2) . . . . ?
O4 C17 C18 C21 -123.3(2) . . . . ?
N1 C2 C3 C4 -0.4(3) . . . . ?
N1 C2 C3 C8 179.67(15) . . . . ?
N1 C2 C14 S1 0.2(2) . . . . ?
N1 C2 C14 C13 179.61(15) . . . . ?
N2 N3 C15 O3 -15.7(3) . . . . ?
N2 N3 C15 C16A 173.7(4) . . . . ?
N2 N3 C15 C16B 158.0(4) . . . . ?
N2 C17 C18 C19 172.31(19) . . . . ?
N2 C17 C18 C20 -69.7(3) . . . . ?
N2 C17 C18 C21 54.8(3) . . . . ?
N3 N2 C1 S1 176.29(14) . . . . ?
N3 N2 C1 N1 -5.7(3) . . . . ?
N3 N2 C17 O4 -172.70(18) . . . . ?
N3 N2 C17 C18 9.1(3) . . . . ?
C1 S1 C14 C2 -0.55(14) . . . . ?
C1 S1 C14 C13 -179.95(17) . . . . ?
C1 N1 C2 C3 -179.68(17) . . . . ?
C1 N1 C2 C14 0.5(2) . . . . ?
C1 N2 N3 C15 -73.0(2) . . . . ?
C1 N2 C17 O4 3.0(3) . . . . ?
C1 N2 C17 C18 -175.19(17) . . . . ?
C2 N1 C1 S1 -1.0(2) . . . . ?
C2 N1 C1 N2 -179.02(16) . . . . ?
C2 C3 C4 C5 -179.37(17) . . . . ?
C2 C3 C8 C7 179.61(15) . . . . ?
C2 C3 C8 C9 0.6(2) . . . . ?
C3 C2 C14 S1 -179.67(13) . . . . ?
C3 C2 C14 C13 -0.2(3) . . . . ?
C3 C4 C5 C6 -0.5(3) . . . . ?
C3 C8 C9 C10 -179.36(16) . . . . ?
C3 C8 C9 C13 0.1(2) . . . . ?
C4 C3 C8 C7 -0.3(2) . . . . ?
C4 C3 C8 C9 -179.39(15) . . . . ?
C4 C5 C6 Cl1 179.53(14) . . . . ?
C4 C5 C6 C7 0.2(3) . . . . ?
C5 C6 C7 C8 0.0(3) . . . . ?
C6 C7 C8 C3 0.1(2) . . . . ?
C6 C7 C8 C9 179.11(16) . . . . ?
C7 C8 C9 C10 1.6(3) . . . . ?
C7 C8 C9 C13 -178.89(16) . . . . ?
C8 C3 C4 C5 0.6(3) . . . . ?
C8 C9 C10 O2 1.1(3) . . . . ?
C8 C9 C10 C11 -179.04(16) . . . . ?
C8 C9 C13 O1 179.08(15) . . . . ?
C8 C9 C13 C14 -0.9(2) . . . . ?
C9 C10 C11 C12 -0.8(3) . . . . ?
C9 C13 C14 S1 -179.71(14) . . . . ?
C9 C13 C14 C2 0.9(3) . . . . ?
C10 C9 C13 O1 -1.4(3) . . . . ?
C10 C9 C13 C14 178.64(16) . . . . ?
C10 C11 C12 O1 -0.1(3) . . . . ?
C10 C11 C12 C22 -179.94(18) . . . . ?
C12 O1 C13 C9 0.5(2) . . . . ?
C12 O1 C13 C14 -179.58(15) . . . . ?
C13 O1 C12 C11 0.4(2) . . . . ?
C13 O1 C12 C22 -179.81(15) . . . . ?
C13 C9 C10 O2 -178.34(17) . . . . ?
C13 C9 C10 C11 1.5(2) . . . . ?
C14 S1 C1 N1 0.91(15) . . . . ?
C14 S1 C1 N2 178.94(16) . . . . ?
C14 C2 C3 C4 179.45(17) . . . . ?
C14 C2 C3 C8 -0.5(2) . . . . ?
C17 N2 N3 C15 103.0(2) . . . . ?
C17 N2 C1 S1 0.3(3) . . . . ?
C17 N2 C1 N1 178.30(18) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.166 0.000 -0.019 266.3 85.7 ?
2 0.334 0.500 -0.359 266.3 87.0 ?
3 0.666 0.500 0.702 266.3 85.7 ?
4 0.834 0.000 0.159 266.3 87.0 ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.752
_oxdiff_exptl_absorpt_empirical_full_min 0.788
