# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2021

####################################################################### 
# 
# 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_202009184
_database_code_depnum_ccdc_archive 'CCDC 2095172'
loop_
_audit_author_name
_audit_author_address
'Jian-Qiang Zhao'
;Chengdu University
China
;
_audit_update_record             
;
2021-07-08 deposited with the CCDC.	2021-09-16 downloaded from the CCDC.
;
_audit_creation_date             2020-09-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H13 Cl N2 O4 S, C2 H6 O S'
_chemical_formula_sum            'C20 H19 Cl N2 O5 S2'
_chemical_formula_weight         466.94
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         C30H30O2P2N2S1Cl1
_chemical_oxdiff_usercomment     r
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           5
_space_group_name_H-M_alt        'C 1 2 1'
_space_group_name_Hall           'C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   26.7417(6)
_cell_length_b                   6.38250(16)
_cell_length_c                   12.8324(3)
_cell_angle_alpha                90
_cell_angle_beta                 103.440(2)
_cell_angle_gamma                90
_cell_volume                     2130.24(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3703
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.7600
_cell_measurement_theta_min      4.2860
_shelx_estimated_absorpt_T_max   0.730
_shelx_estimated_absorpt_T_min   0.570
_exptl_absorpt_coefficient_mu    3.728
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68838
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.456
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             968
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_av_unetI/netI     0.0422
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7977
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.054
_diffrn_reflns_theta_max         67.054
_diffrn_reflns_theta_min         3.398
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -108.00 -32.00   1.00    1.50    --  -33.50 178.00  60.00   76
  2  ω   -104.00 -11.00   1.00    1.50    --  -33.50 -37.00 -30.00   93
  3  ω     57.00 110.00   1.00    1.50    --   36.47 178.00  60.00   53
  4  ω     57.00 110.00   1.00    1.50    --   36.47 178.00 -30.00   53
  5  ω     -4.00  77.00   1.00    1.50    --   36.47 -99.00  60.00   81
  6  ω     57.00 110.00   1.00    1.50    --   36.47 178.00-150.00   53
  7  ω     57.00  82.00   1.00    1.50    --   36.47 178.00 -90.00   25
  8  ω    102.00 172.00   1.00    5.00    --  108.00 111.00 150.00   70
  9  ω     53.00  92.00   1.00    5.00    --  108.00 -94.00  90.00   39
 10  ω    122.00 174.00   1.00    5.00    --  108.00  61.00 -30.00   52
 11  ω     90.00 118.00   1.00    5.00    --  108.00 -45.00-120.00   28
 12  ω     43.00  69.00   1.00    5.00    --  108.00 -45.00-120.00   26
 13  ω     44.00 137.00   1.00    5.00    --  108.00 -77.00-180.00   93
 14  ω     43.00  88.00   1.00    5.00    --  108.00 -45.00   0.00   45
 15  ω     84.00 173.00   1.00    5.00    --  108.00  77.00 -60.00   89
 16  ω    119.00 148.00   1.00    5.00    --  108.00 178.00 150.00   29
 17  ω     58.00  84.00   1.00    5.00    --  108.00 178.00 150.00   26
 18  ω    -59.00 -32.00   1.00    1.50    --  -33.50 178.00 -90.00   27
 19  ω    -22.00   4.00   1.00    1.50    --   36.47 -19.00-150.00   26
 20  ω      2.00  59.00   1.00    1.50    --   36.47 -37.00 150.00   57
 21  ω     29.00  54.00   1.00    1.50    --   36.47  57.00 -60.00   25
 22  ω     52.00  77.00   1.00    1.50    --   36.47 -99.00-150.00   25
 23  ω     76.00 102.00   1.00    1.50    --   36.47  57.00 -60.00   26
 24  ω      7.00  63.00   1.00    1.50    --   36.47 -19.00-150.00   56
 25  ω    119.00 174.00   1.00    3.50    --  108.00  77.00 -90.00   55
 26  ω     84.00 110.00   1.00    3.50    --  108.00  77.00 -90.00   26
 27  ω    109.00 169.00   1.00    3.50    --  108.00  45.00  90.00   60
 28  ω    102.00 128.00   1.00    3.50    --  108.00 111.00  90.00   26
 29  ω    131.00 168.00   1.00    3.50    --  108.00 111.00  90.00   37
 30  ω     52.00  99.00   1.00    3.50    --  108.00 -96.00-174.00   47
 31  ω     92.00 170.00   1.00    3.50    --  108.00  15.00  60.00   78
 32  ω     74.00 124.00   1.00    3.50    --  108.00 -45.00 150.00   50
 33  ω     81.00 110.00   1.00    3.50    --  108.00 -94.00 -90.00   29
 34  ω    145.00 176.00   1.00    3.50    --  108.00  61.00   0.00   31
 35  ω     88.00 115.00   1.00    3.50    --  108.00  61.00   0.00   27
 36  ω     41.00 109.00   1.00    3.50    --  108.00-111.00 150.00   68
 37  ω     80.00 105.00   1.00    1.50    --   36.47  57.00  30.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0091061000
_diffrn_orient_matrix_UB_12      0.1124765000
_diffrn_orient_matrix_UB_13      -0.1090215000
_diffrn_orient_matrix_UB_21      -0.0187058000
_diffrn_orient_matrix_UB_22      0.1961213000
_diffrn_orient_matrix_UB_23      0.0497723000
_diffrn_orient_matrix_UB_31      0.0554522000
_diffrn_orient_matrix_UB_32      0.0846094000
_diffrn_orient_matrix_UB_33      0.0295007000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.821
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                3549
_reflns_number_total             3813
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.459
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details 
;
 Flack x determined using 1465 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.001(14)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     278
_refine_ls_number_reflns         3813
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0462
_refine_ls_R_factor_gt           0.0425
_refine_ls_restrained_S_all      1.027
_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)+(0.0679P)²+0.4992P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1083
_refine_ls_wR_factor_ref         0.1133
_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.a Ternary CH refined with riding coordinates:
 C5(H5)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C11(H11), C14(H14), C15(H15), C16(H16), C17(H17), C18(H18)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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
C1 C 0.70569(15) 0.2640(7) 0.1012(3) 0.0387(9) Uani 1 1 d . . . . .
C2 C 0.66813(14) 0.2981(7) -0.0084(3) 0.0366(8) Uani 1 1 d . . . . .
C3 C 0.62517(14) 0.3316(6) 0.1346(3) 0.0330(8) Uani 1 1 d . . . . .
C4 C 0.62316(14) 0.5545(6) 0.0803(3) 0.0335(8) Uani 1 1 d . . . . .
C5 C 0.65393(14) 0.5371(7) -0.0081(3) 0.0350(8) Uani 1 1 d . . . . .
H5 H 0.6847 0.6259 0.0076 0.042 Uiso 1 1 calc R . . . .
C6 C 0.61459(15) 0.6149(6) -0.1042(3) 0.0360(8) Uani 1 1 d . . . . .
C7 C 0.56953(14) 0.6559(7) -0.0731(3) 0.0348(8) Uani 1 1 d . . . . .
C8 C 0.52571(15) 0.7279(6) -0.1427(3) 0.0384(9) Uani 1 1 d . . . . .
H8 H 0.4959 0.7563 -0.1196 0.046 Uiso 1 1 calc R . . . .
C9 C 0.52787(16) 0.7561(8) -0.2481(3) 0.0449(10) Uani 1 1 d . . . . .
H9 H 0.4988 0.8002 -0.2982 0.054 Uiso 1 1 calc R . . . .
C10 C 0.57297(17) 0.7190(8) -0.2794(3) 0.0473(11) Uani 1 1 d . . . . .
C11 C 0.61765(16) 0.6490(8) -0.2085(3) 0.0438(9) Uani 1 1 d . . . . .
H11 H 0.6480 0.6265 -0.2306 0.053 Uiso 1 1 calc R . . . .
C12 C 0.68680(19) 0.2229(8) -0.1039(4) 0.0533(12) Uani 1 1 d . . . . .
H12A H 0.6974 0.0793 -0.0934 0.080 Uiso 1 1 calc GR . . . .
H12B H 0.7154 0.3072 -0.1121 0.080 Uiso 1 1 calc GR . . . .
H12C H 0.6595 0.2342 -0.1672 0.080 Uiso 1 1 calc GR . . . .
C13 C 0.59034(15) 0.3040(6) 0.2109(3) 0.0346(8) Uani 1 1 d . . . . .
C14 C 0.53820(16) 0.2640(7) 0.1711(4) 0.0436(9) Uani 1 1 d . . . . .
H14 H 0.5252 0.2475 0.0978 0.052 Uiso 1 1 calc R . . . .
C15 C 0.50572(17) 0.2486(8) 0.2400(4) 0.0499(11) Uani 1 1 d . . . . .
H15 H 0.4709 0.2225 0.2128 0.060 Uiso 1 1 calc R . . . .
C16 C 0.52429(19) 0.2713(10) 0.3480(4) 0.0579(13) Uani 1 1 d . . . . .
H16 H 0.5022 0.2607 0.3941 0.069 Uiso 1 1 calc R . . . .
C17 C 0.5759(2) 0.3101(11) 0.3882(4) 0.0622(14) Uani 1 1 d . . . . .
H17 H 0.5886 0.3247 0.4617 0.075 Uiso 1 1 calc R . . . .
C18 C 0.60888(17) 0.3274(9) 0.3203(4) 0.0491(11) Uani 1 1 d . . . . .
H18 H 0.6436 0.3548 0.3481 0.059 Uiso 1 1 calc R . . . .
Cl1 Cl 0.57321(5) 0.7586(4) -0.41423(10) 0.0835(6) Uani 1 1 d . . . . .
N1 N 0.67920(12) 0.2853(6) 0.1779(3) 0.0369(7) Uani 1 1 d . . . . .
H1 H 0.6930(19) 0.298(9) 0.244(4) 0.047(14) Uiso 1 1 d . . . . .
N2 N 0.64511(13) 0.7152(5) 0.1678(3) 0.0395(8) Uani 1 1 d . . . . .
O1 O 0.75162(11) 0.2316(6) 0.1145(3) 0.0550(9) Uani 1 1 d . . . . .
O2 O 0.57275(10) 0.6163(4) 0.0337(2) 0.0357(6) Uani 1 1 d . . . . .
O3 O 0.61521(14) 0.7952(6) 0.2138(3) 0.0539(8) Uani 1 1 d . . . . .
O4 O 0.69135(12) 0.7476(6) 0.1886(3) 0.0574(9) Uani 1 1 d . . . . .
S1 S 0.60991(4) 0.16740(15) 0.01305(7) 0.0378(2) Uani 1 1 d . . . . .
C19 C 0.3052(3) 1.0998(17) 0.3794(6) 0.110(4) Uani 1 1 d . . . . .
H19A H 0.2881 1.1353 0.3072 0.165 Uiso 1 1 calc GR . . . .
H19B H 0.3417 1.1159 0.3884 0.165 Uiso 1 1 calc GR . . . .
H19C H 0.2935 1.1909 0.4283 0.165 Uiso 1 1 calc GR . . . .
C20 C 0.3182(2) 0.8387(13) 0.5462(4) 0.0704(16) Uani 1 1 d . . . . .
H20A H 0.3035 0.9523 0.5781 0.106 Uiso 1 1 calc GR . . . .
H20B H 0.3547 0.8580 0.5587 0.106 Uiso 1 1 calc GR . . . .
H20C H 0.3111 0.7088 0.5776 0.106 Uiso 1 1 calc GR . . . .
O5 O 0.23362(14) 0.8293(9) 0.3946(3) 0.0749(13) Uani 1 1 d . . . . .
S2 S 0.29096(5) 0.8334(3) 0.40611(10) 0.0737(5) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.542(5) . ?
C1 N1 1.347(5) . ?
C1 O1 1.218(5) . ?
C2 C5 1.573(6) . ?
C2 C12 1.505(6) . ?
C2 S1 1.842(4) . ?
C3 C4 1.580(5) . ?
C3 C13 1.510(5) . ?
C3 N1 1.453(5) . ?
C3 S1 1.845(4) . ?
C4 C5 1.553(5) . ?
C4 N2 1.533(5) . ?
C4 O2 1.398(4) . ?
C5 H5 0.9800 . ?
C5 C6 1.507(5) . ?
C6 C7 1.380(6) . ?
C6 C11 1.376(6) . ?
C7 C8 1.376(5) . ?
C7 O2 1.376(5) . ?
C8 H8 0.9300 . ?
C8 C9 1.379(6) . ?
C9 H9 0.9300 . ?
C9 C10 1.377(7) . ?
C10 C11 1.396(6) . ?
C10 Cl1 1.750(4) . ?
C11 H11 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.393(6) . ?
C13 C18 1.385(6) . ?
C14 H14 0.9300 . ?
C14 C15 1.380(6) . ?
C15 H15 0.9300 . ?
C15 C16 1.366(7) . ?
C16 H16 0.9300 . ?
C16 C17 1.378(8) . ?
C17 H17 0.9300 . ?
C17 C18 1.381(7) . ?
C18 H18 0.9300 . ?
N1 H1 0.84(5) . ?
N2 O3 1.212(5) . ?
N2 O4 1.221(4) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C19 S2 1.793(10) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C20 S2 1.777(5) . ?
O5 S2 1.506(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
N1 C1 C2 108.1(3) . . ?
O1 C1 C2 125.0(4) . . ?
O1 C1 N1 126.8(4) . . ?
C1 C2 C5 103.9(3) . . ?
C1 C2 S1 101.2(3) . . ?
C5 C2 S1 103.1(2) . . ?
C12 C2 C1 115.4(3) . . ?
C12 C2 C5 115.9(4) . . ?
C12 C2 S1 115.4(3) . . ?
C4 C3 S1 99.2(2) . . ?
C13 C3 C4 115.3(3) . . ?
C13 C3 S1 115.7(3) . . ?
N1 C3 C4 106.3(3) . . ?
N1 C3 C13 115.9(3) . . ?
N1 C3 S1 102.3(3) . . ?
C5 C4 C3 106.8(3) . . ?
N2 C4 C3 108.1(3) . . ?
N2 C4 C5 113.9(3) . . ?
O2 C4 C3 111.9(3) . . ?
O2 C4 C5 109.2(3) . . ?
O2 C4 N2 107.0(3) . . ?
C2 C5 H5 111.7 . . ?
C4 C5 C2 103.9(3) . . ?
C4 C5 H5 111.7 . . ?
C6 C5 C2 116.2(3) . . ?
C6 C5 C4 100.8(3) . . ?
C6 C5 H5 111.7 . . ?
C7 C6 C5 108.4(3) . . ?
C11 C6 C5 131.3(4) . . ?
C11 C6 C7 120.3(4) . . ?
C8 C7 C6 123.0(4) . . ?
O2 C7 C6 113.3(3) . . ?
O2 C7 C8 123.6(4) . . ?
C7 C8 H8 121.4 . . ?
C7 C8 C9 117.1(4) . . ?
C9 C8 H8 121.4 . . ?
C8 C9 H9 119.9 . . ?
C10 C9 C8 120.2(4) . . ?
C10 C9 H9 119.9 . . ?
C9 C10 C11 122.7(4) . . ?
C9 C10 Cl1 117.9(3) . . ?
C11 C10 Cl1 119.4(3) . . ?
C6 C11 C10 116.7(4) . . ?
C6 C11 H11 121.7 . . ?
C10 C11 H11 121.7 . . ?
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 . . ?
C14 C13 C3 120.0(3) . . ?
C18 C13 C3 121.0(4) . . ?
C18 C13 C14 118.9(4) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 C13 120.3(4) . . ?
C15 C14 H14 119.9 . . ?
C14 C15 H15 119.7 . . ?
C16 C15 C14 120.5(4) . . ?
C16 C15 H15 119.7 . . ?
C15 C16 H16 120.2 . . ?
C15 C16 C17 119.7(4) . . ?
C17 C16 H16 120.2 . . ?
C16 C17 H17 119.7 . . ?
C16 C17 C18 120.6(5) . . ?
C18 C17 H17 119.7 . . ?
C13 C18 H18 120.0 . . ?
C17 C18 C13 120.0(4) . . ?
C17 C18 H18 120.0 . . ?
C1 N1 C3 112.7(3) . . ?
C1 N1 H1 124(3) . . ?
C3 N1 H1 122(3) . . ?
O3 N2 C4 117.1(3) . . ?
O3 N2 O4 124.8(4) . . ?
O4 N2 C4 118.1(3) . . ?
C7 O2 C4 108.0(3) . . ?
C2 S1 C3 80.83(17) . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
S2 C19 H19A 109.5 . . ?
S2 C19 H19B 109.5 . . ?
S2 C19 H19C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
S2 C20 H20A 109.5 . . ?
S2 C20 H20B 109.5 . . ?
S2 C20 H20C 109.5 . . ?
C20 S2 C19 96.9(4) . . ?
O5 S2 C19 104.7(4) . . ?
O5 S2 C20 105.6(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
N1 H1 O5 0.84(5) 2.00(5) 2.837(5) 173(5) 3_545

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
C1 C2 C5 C4 -66.8(3) . . . . ?
C1 C2 C5 C6 -176.4(3) . . . . ?
C1 C2 S1 C3 49.4(3) . . . . ?
C2 C1 N1 C3 0.1(5) . . . . ?
C2 C5 C6 C7 108.7(4) . . . . ?
C2 C5 C6 C11 -72.0(6) . . . . ?
C3 C4 C5 C2 5.1(4) . . . . ?
C3 C4 C5 C6 125.8(3) . . . . ?
C3 C4 N2 O3 -88.7(4) . . . . ?
C3 C4 N2 O4 88.6(4) . . . . ?
C3 C4 O2 C7 -122.8(3) . . . . ?
C3 C13 C14 C15 -176.9(4) . . . . ?
C3 C13 C18 C17 177.3(5) . . . . ?
C4 C3 C13 C14 79.8(5) . . . . ?
C4 C3 C13 C18 -97.2(5) . . . . ?
C4 C3 N1 C1 -65.2(4) . . . . ?
C4 C3 S1 C2 58.8(2) . . . . ?
C4 C5 C6 C7 -2.8(4) . . . . ?
C4 C5 C6 C11 176.5(5) . . . . ?
C5 C2 S1 C3 -57.9(3) . . . . ?
C5 C4 N2 O3 152.7(4) . . . . ?
C5 C4 N2 O4 -29.9(5) . . . . ?
C5 C4 O2 C7 -4.7(4) . . . . ?
C5 C6 C7 C8 -179.4(4) . . . . ?
C5 C6 C7 O2 0.1(5) . . . . ?
C5 C6 C11 C10 178.8(4) . . . . ?
C6 C7 C8 C9 0.9(6) . . . . ?
C6 C7 O2 C4 3.0(5) . . . . ?
C7 C6 C11 C10 -2.0(7) . . . . ?
C7 C8 C9 C10 -2.1(7) . . . . ?
C8 C7 O2 C4 -177.5(4) . . . . ?
C8 C9 C10 C11 1.2(8) . . . . ?
C8 C9 C10 Cl1 -179.8(4) . . . . ?
C9 C10 C11 C6 0.9(8) . . . . ?
C11 C6 C7 C8 1.2(7) . . . . ?
C11 C6 C7 O2 -179.3(4) . . . . ?
C12 C2 C5 C4 165.5(3) . . . . ?
C12 C2 C5 C6 55.8(5) . . . . ?
C12 C2 S1 C3 174.7(4) . . . . ?
C13 C3 C4 C5 -170.4(3) . . . . ?
C13 C3 C4 N2 66.6(4) . . . . ?
C13 C3 C4 O2 -51.0(4) . . . . ?
C13 C3 N1 C1 165.1(4) . . . . ?
C13 C3 S1 C2 -177.2(3) . . . . ?
C13 C14 C15 C16 -0.3(8) . . . . ?
C14 C13 C18 C17 0.3(7) . . . . ?
C14 C15 C16 C17 0.0(9) . . . . ?
C15 C16 C17 C18 0.4(10) . . . . ?
C16 C17 C18 C13 -0.6(9) . . . . ?
C18 C13 C14 C15 0.2(7) . . . . ?
Cl1 C10 C11 C6 -178.1(4) . . . . ?
N1 C1 C2 C5 68.2(4) . . . . ?
N1 C1 C2 C12 -163.7(4) . . . . ?
N1 C1 C2 S1 -38.4(4) . . . . ?
N1 C3 C4 C5 59.6(4) . . . . ?
N1 C3 C4 N2 -63.4(4) . . . . ?
N1 C3 C4 O2 179.0(3) . . . . ?
N1 C3 C13 C14 -155.1(4) . . . . ?
N1 C3 C13 C18 27.9(6) . . . . ?
N1 C3 S1 C2 -50.3(3) . . . . ?
N2 C4 C5 C2 124.4(3) . . . . ?
N2 C4 C5 C6 -115.0(3) . . . . ?
N2 C4 O2 C7 119.0(3) . . . . ?
O1 C1 C2 C5 -109.3(5) . . . . ?
O1 C1 C2 C12 18.7(7) . . . . ?
O1 C1 C2 S1 144.1(4) . . . . ?
O1 C1 N1 C3 177.6(5) . . . . ?
O2 C4 C5 C2 -116.1(3) . . . . ?
O2 C4 C5 C6 4.6(4) . . . . ?
O2 C4 N2 O3 32.0(5) . . . . ?
O2 C4 N2 O4 -150.6(4) . . . . ?
O2 C7 C8 C9 -178.6(4) . . . . ?
S1 C2 C5 C4 38.4(3) . . . . ?
S1 C2 C5 C6 -71.2(4) . . . . ?
S1 C3 C4 C5 -46.2(3) . . . . ?
S1 C3 C4 N2 -169.1(2) . . . . ?
S1 C3 C4 O2 73.3(3) . . . . ?
S1 C3 C13 C14 -35.3(5) . . . . ?
S1 C3 C13 C18 147.7(4) . . . . ?
S1 C3 N1 C1 38.3(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 2.021
_oxdiff_exptl_absorpt_empirical_full_min 0.805
