# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 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_YMD_56B_0m
_audit_block_doi                 10.5517/ccdc.csd.cc278ts4
_database_code_depnum_ccdc_archive 'CCDC 2064066'
loop_
_audit_author_name
_audit_author_address
'Matthias Zeller'
;Purdue University, Department of Chemistry
United States of America
;
_audit_update_record             
;
2021-02-20 deposited with the CCDC.	2021-05-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H16 Cl N O3 S'
_chemical_formula_weight         361.83

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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.07070(10)
_cell_length_b                   18.5864(3)
_cell_length_c                   11.3791(2)
_cell_angle_alpha                90
_cell_angle_beta                 101.7890(6)
_cell_angle_gamma                90
_cell_volume                     1670.92(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    8472
_cell_measurement_theta_min      4.6279
_cell_measurement_theta_max      79.8273

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_F_000             752
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    3.333
_shelx_estimated_absorpt_T_min   0.618
_shelx_estimated_absorpt_T_max   0.671
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6506
_exptl_absorpt_correction_T_max  0.7543
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'I-mu-S microsource X-ray tube'
_diffrn_source_current           '1.0 mA'
_diffrn_source_voltage           '50 kV'
_diffrn_radiation_monochromator  'laterally graded multilayer (Goebel) mirror'
_diffrn_measurement_device_type  
;
Bruker AXS D8 Quest diffractometer with PhotonIII_C14 charge-integrating and 
photon counting pixel array detector
;
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean 7.4074
_diffrn_reflns_number            11442
_diffrn_reflns_av_unetI/netI     0.0209
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.628
_diffrn_reflns_theta_max         79.819
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.945
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.945
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.945
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             3446
_reflns_number_gt                3311
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Apex3 v2019.1-0 (Bruker, 2019)'
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  
;  
SHELXL-2018/3 (Sheldrick, 2015, 2018), 
SHELXLE Rev1149 (Hübschle et al., 2011)
;
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0356P)²+1.1140P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0020(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3446
_refine_ls_number_parameters     219
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0320
_refine_ls_R_factor_gt           0.0307
_refine_ls_wR_factor_ref         0.0801
_refine_ls_wR_factor_gt          0.0792
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.36050(5) 0.14334(2) 0.91653(3) 0.02523(11) Uani 1 1 d . . . . .
S1 S 0.67472(4) 0.04972(2) 0.67733(3) 0.01904(11) Uani 1 1 d . . . . .
O1 O 0.52082(13) 0.19827(6) 0.66714(10) 0.0247(2) Uani 1 1 d . . . . .
O2 O 0.76191(13) 0.09257(7) 0.60542(10) 0.0267(3) Uani 1 1 d . . . . .
O3 O 0.66724(14) -0.02684(6) 0.66262(10) 0.0261(2) Uani 1 1 d . . . . .
N1 N 0.47299(15) 0.07542(7) 0.64905(11) 0.0189(3) Uani 1 1 d . . . . .
C1 C 0.42517(18) 0.14765(8) 0.65685(12) 0.0188(3) Uani 1 1 d . . . . .
C2 C 0.23790(18) 0.14889(8) 0.65020(13) 0.0191(3) Uani 1 1 d . . . . .
C3 C 0.18206(19) 0.07091(8) 0.64513(14) 0.0222(3) Uani 1 1 d . . . . .
H3 H 0.089741 0.056824 0.687300 0.027 Uiso 1 1 calc R U . . .
C4 C 0.33757(18) 0.02374(8) 0.66007(14) 0.0219(3) Uani 1 1 d . . . . .
H4A H 0.360997 -0.000067 0.739575 0.026 Uiso 1 1 calc R U . . .
H4B H 0.324588 -0.013442 0.596541 0.026 Uiso 1 1 calc R U . . .
C5 C 0.1378(2) 0.11646(9) 0.53492(14) 0.0260(3) Uani 1 1 d . . . . .
H5A H 0.018212 0.131397 0.508439 0.031 Uiso 1 1 calc R U . . .
H5B H 0.198373 0.107137 0.469087 0.031 Uiso 1 1 calc R U . . .
C6 C 0.17279(18) 0.20661(8) 0.71938(13) 0.0192(3) Uani 1 1 d . . . . .
C7 C 0.22479(18) 0.21018(8) 0.84383(13) 0.0195(3) Uani 1 1 d . . . . .
C8 C 0.17132(19) 0.26408(8) 0.91167(14) 0.0234(3) Uani 1 1 d . . . . .
H8 H 0.210474 0.265674 0.996239 0.028 Uiso 1 1 calc R U . . .
C9 C 0.0596(2) 0.31563(9) 0.85372(15) 0.0275(3) Uani 1 1 d . . . . .
H9 H 0.021077 0.352847 0.898741 0.033 Uiso 1 1 calc R U . . .
C10 C 0.0041(2) 0.31296(9) 0.73046(16) 0.0302(4) Uani 1 1 d . . . . .
H10 H -0.073634 0.347993 0.691172 0.036 Uiso 1 1 calc R U . . .
C11 C 0.0617(2) 0.25906(9) 0.66376(14) 0.0259(3) Uani 1 1 d . . . . .
H11 H 0.024407 0.258223 0.578994 0.031 Uiso 1 1 calc R U . . .
C12 C 0.75176(18) 0.06963(8) 0.82952(13) 0.0193(3) Uani 1 1 d . . . . .
C13 C 0.81482(19) 0.13785(8) 0.86390(14) 0.0234(3) Uani 1 1 d . . . . .
H13 H 0.818977 0.173818 0.805268 0.028 Uiso 1 1 calc R U . . .
C14 C 0.8713(2) 0.15252(9) 0.98463(14) 0.0250(3) Uani 1 1 d . . . . .
H14 H 0.912794 0.199241 1.008499 0.030 Uiso 1 1 calc R U . . .
C15 C 0.86873(19) 0.10009(9) 1.07217(14) 0.0230(3) Uani 1 1 d . . . . .
C16 C 0.8059(2) 0.03236(9) 1.03533(14) 0.0279(3) Uani 1 1 d . . . . .
H16 H 0.803766 -0.003927 1.093799 0.034 Uiso 1 1 calc R U . . .
C17 C 0.7462(2) 0.01663(8) 0.91499(14) 0.0256(3) Uani 1 1 d . . . . .
H17 H 0.702020 -0.029708 0.891218 0.031 Uiso 1 1 calc R U . . .
C18 C 0.9360(2) 0.11650(9) 1.20302(14) 0.0300(4) Uani 1 1 d . . . . .
H18A H 0.979703 0.165844 1.211229 0.045 Uiso 1 1 calc R U . . .
H18B H 1.027456 0.082835 1.235367 0.045 Uiso 1 1 calc R U . . .
H18C H 0.844720 0.111498 1.247493 0.045 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C7 1.7484(15) . ?
S1 O2 1.4262(11) . ?
S1 O3 1.4327(12) . ?
S1 N1 1.6638(12) . ?
S1 C12 1.7557(15) . ?
O1 C1 1.2075(18) . ?
N1 C1 1.4047(19) . ?
N1 C4 1.4795(19) . ?
C1 C2 1.4980(19) . ?
C2 C6 1.4884(19) . ?
C2 C3 1.515(2) . ?
C2 C5 1.518(2) . ?
C3 C5 1.495(2) . ?
C3 C4 1.512(2) . ?
C3 H3 1.0000 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C11 1.387(2) . ?
C6 C7 1.394(2) . ?
C7 C8 1.386(2) . ?
C8 C9 1.387(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.383(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.393(2) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 C17 1.391(2) . ?
C12 C13 1.392(2) . ?
C13 C14 1.383(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.397(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.390(2) . ?
C15 C18 1.508(2) . ?
C16 C17 1.387(2) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 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
O2 S1 O3 120.11(7) . . ?
O2 S1 N1 107.86(6) . . ?
O3 S1 N1 104.26(6) . . ?
O2 S1 C12 109.35(7) . . ?
O3 S1 C12 108.81(7) . . ?
N1 S1 C12 105.40(6) . . ?
C1 N1 C4 113.45(11) . . ?
C1 N1 S1 122.19(10) . . ?
C4 N1 S1 120.52(10) . . ?
O1 C1 N1 124.92(13) . . ?
O1 C1 C2 127.69(13) . . ?
N1 C1 C2 107.39(12) . . ?
C6 C2 C1 116.48(12) . . ?
C6 C2 C3 125.11(12) . . ?
C1 C2 C3 106.04(12) . . ?
C6 C2 C5 124.06(13) . . ?
C1 C2 C5 113.02(12) . . ?
C3 C2 C5 59.04(10) . . ?
C5 C3 C4 118.26(13) . . ?
C5 C3 C2 60.56(10) . . ?
C4 C3 C2 108.47(12) . . ?
C5 C3 H3 118.5 . . ?
C4 C3 H3 118.5 . . ?
C2 C3 H3 118.5 . . ?
N1 C4 C3 102.98(12) . . ?
N1 C4 H4A 111.2 . . ?
C3 C4 H4A 111.2 . . ?
N1 C4 H4B 111.2 . . ?
C3 C4 H4B 111.2 . . ?
H4A C4 H4B 109.1 . . ?
C3 C5 C2 60.39(10) . . ?
C3 C5 H5A 117.7 . . ?
C2 C5 H5A 117.7 . . ?
C3 C5 H5B 117.7 . . ?
C2 C5 H5B 117.7 . . ?
H5A C5 H5B 114.9 . . ?
C11 C6 C7 117.55(13) . . ?
C11 C6 C2 122.04(13) . . ?
C7 C6 C2 120.40(13) . . ?
C8 C7 C6 122.47(14) . . ?
C8 C7 Cl1 119.09(12) . . ?
C6 C7 Cl1 118.44(11) . . ?
C7 C8 C9 118.73(14) . . ?
C7 C8 H8 120.6 . . ?
C9 C8 H8 120.6 . . ?
C10 C9 C8 120.12(15) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C9 C10 C11 120.22(15) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C6 C11 C10 120.91(15) . . ?
C6 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
C17 C12 C13 120.69(14) . . ?
C17 C12 S1 118.99(12) . . ?
C13 C12 S1 120.31(12) . . ?
C14 C13 C12 119.09(14) . . ?
C14 C13 H13 120.5 . . ?
C12 C13 H13 120.5 . . ?
C13 C14 C15 121.38(15) . . ?
C13 C14 H14 119.3 . . ?
C15 C14 H14 119.3 . . ?
C16 C15 C14 118.34(14) . . ?
C16 C15 C18 121.12(14) . . ?
C14 C15 C18 120.53(14) . . ?
C17 C16 C15 121.38(15) . . ?
C17 C16 H16 119.3 . . ?
C15 C16 H16 119.3 . . ?
C16 C17 C12 119.12(15) . . ?
C16 C17 H17 120.4 . . ?
C12 C17 H17 120.4 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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
O2 S1 N1 C1 -52.82(13) . . . . ?
O3 S1 N1 C1 178.45(11) . . . . ?
C12 S1 N1 C1 63.92(12) . . . . ?
O2 S1 N1 C4 150.69(11) . . . . ?
O3 S1 N1 C4 21.96(13) . . . . ?
C12 S1 N1 C4 -92.57(12) . . . . ?
C4 N1 C1 O1 169.08(14) . . . . ?
S1 N1 C1 O1 11.1(2) . . . . ?
C4 N1 C1 C2 -10.83(16) . . . . ?
S1 N1 C1 C2 -168.83(9) . . . . ?
O1 C1 C2 C6 -32.4(2) . . . . ?
N1 C1 C2 C6 147.47(12) . . . . ?
O1 C1 C2 C3 -176.71(14) . . . . ?
N1 C1 C2 C3 3.20(15) . . . . ?
O1 C1 C2 C5 120.63(17) . . . . ?
N1 C1 C2 C5 -59.46(16) . . . . ?
C6 C2 C3 C5 112.13(16) . . . . ?
C1 C2 C3 C5 -107.58(13) . . . . ?
C6 C2 C3 C4 -135.24(14) . . . . ?
C1 C2 C3 C4 5.06(16) . . . . ?
C5 C2 C3 C4 112.63(14) . . . . ?
C1 N1 C4 C3 13.57(16) . . . . ?
S1 N1 C4 C3 171.98(10) . . . . ?
C5 C3 C4 N1 55.10(17) . . . . ?
C2 C3 C4 N1 -10.77(15) . . . . ?
C4 C3 C5 C2 -96.29(14) . . . . ?
C6 C2 C5 C3 -113.83(16) . . . . ?
C1 C2 C5 C3 95.47(13) . . . . ?
C1 C2 C6 C11 117.37(16) . . . . ?
C3 C2 C6 C11 -105.94(18) . . . . ?
C5 C2 C6 C11 -32.4(2) . . . . ?
C1 C2 C6 C7 -61.58(18) . . . . ?
C3 C2 C6 C7 75.11(19) . . . . ?
C5 C2 C6 C7 148.63(15) . . . . ?
C11 C6 C7 C8 -0.8(2) . . . . ?
C2 C6 C7 C8 178.15(14) . . . . ?
C11 C6 C7 Cl1 178.37(12) . . . . ?
C2 C6 C7 Cl1 -2.64(19) . . . . ?
C6 C7 C8 C9 1.2(2) . . . . ?
Cl1 C7 C8 C9 -178.04(12) . . . . ?
C7 C8 C9 C10 -0.3(2) . . . . ?
C8 C9 C10 C11 -0.8(3) . . . . ?
C7 C6 C11 C10 -0.3(2) . . . . ?
C2 C6 C11 C10 -179.30(15) . . . . ?
C9 C10 C11 C6 1.1(3) . . . . ?
O2 S1 C12 C17 -151.60(12) . . . . ?
O3 S1 C12 C17 -18.65(14) . . . . ?
N1 S1 C12 C17 92.68(13) . . . . ?
O2 S1 C12 C13 29.44(14) . . . . ?
O3 S1 C12 C13 162.39(12) . . . . ?
N1 S1 C12 C13 -86.28(13) . . . . ?
C17 C12 C13 C14 -0.3(2) . . . . ?
S1 C12 C13 C14 178.62(12) . . . . ?
C12 C13 C14 C15 1.0(2) . . . . ?
C13 C14 C15 C16 -0.7(2) . . . . ?
C13 C14 C15 C18 178.06(15) . . . . ?
C14 C15 C16 C17 -0.3(3) . . . . ?
C18 C15 C16 C17 -179.02(16) . . . . ?
C15 C16 C17 C12 0.9(3) . . . . ?
C13 C12 C17 C16 -0.6(2) . . . . ?
S1 C12 C17 C16 -179.57(13) . . . . ?

_refine_diff_density_max         0.359
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.047

####################################################################### 
# 
# 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_YMD_67B1_0m
_audit_block_doi                 10.5517/ccdc.csd.cc278tv6
_database_code_depnum_ccdc_archive 'CCDC 2064068'
loop_
_audit_author_name
_audit_author_address
'Matthias Zeller'
;Purdue University, Department of Chemistry
United States of America
;
_audit_update_record             
;
2021-02-20 deposited with the CCDC.	2021-05-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H20 Cl N O3 S'
_chemical_formula_weight         389.88

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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.2711(2)
_cell_length_b                   8.2248(2)
_cell_length_c                   21.6325(4)
_cell_angle_alpha                90
_cell_angle_beta                 95.3585(6)
_cell_angle_gamma                90
_cell_volume                     1819.48(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    8835
_cell_measurement_theta_min      4.3234
_cell_measurement_theta_max      79.3531

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_F_000             816
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    3.101
_shelx_estimated_absorpt_T_min   0.562
_shelx_estimated_absorpt_T_max   0.671
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6053
_exptl_absorpt_correction_T_max  0.7543
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'I-mu-S microsource X-ray tube'
_diffrn_source_current           '1.0 mA'
_diffrn_source_voltage           '50 kV'
_diffrn_radiation_monochromator  'laterally graded multilayer (Goebel) mirror'
_diffrn_measurement_device_type  
;
Bruker AXS D8 Quest diffractometer with PhotonIII_C14 charge-integrating and 
photon counting pixel array detector
;
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean 7.4074
_diffrn_reflns_number            11627
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         4.105
_diffrn_reflns_theta_max         79.806
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.933
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.933
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.933
_diffrn_reflns_point_group_measured_fraction_full 0.985
_reflns_number_total             3703
_reflns_number_gt                3506
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Apex3 v2019.1-0 (Bruker, 2019)'
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  
;  
SHELXL-2018/3 (Sheldrick, 2015, 2018), 
SHELXLE Rev1149 (Hübschle et al., 2011)
;
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0344P)²+1.1524P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0070(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3703
_refine_ls_number_parameters     237
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0348
_refine_ls_R_factor_gt           0.0330
_refine_ls_wR_factor_ref         0.0839
_refine_ls_wR_factor_gt          0.0827
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.77089(4) 0.59946(5) 0.07097(2) 0.03101(13) Uani 1 1 d . . . . .
S1 S 0.25919(3) 0.81018(4) 0.14563(2) 0.01384(11) Uani 1 1 d . . . . .
O1 O 0.49363(10) 0.73363(13) 0.08999(5) 0.0225(2) Uani 1 1 d . . . . .
O2 O 0.33570(10) 0.94823(13) 0.16668(5) 0.0203(2) Uani 1 1 d . . . . .
O3 O 0.14334(10) 0.77399(14) 0.17547(5) 0.0204(2) Uani 1 1 d . . . . .
N1 N 0.34962(11) 0.64009(15) 0.15502(5) 0.0145(2) Uani 1 1 d . . . . .
C1 C 0.45712(13) 0.62122(18) 0.12027(6) 0.0149(3) Uani 1 1 d . . . . .
C2 C 0.52220(13) 0.45522(18) 0.12307(6) 0.0150(3) Uani 1 1 d . . . . .
C3 C 0.43776(14) 0.30406(18) 0.11659(7) 0.0172(3) Uani 1 1 d . . . . .
H3 H 0.471003 0.206779 0.140906 0.021 Uiso 1 1 calc R U . . .
C4 C 0.29061(14) 0.32487(19) 0.10785(7) 0.0194(3) Uani 1 1 d . . . . .
H4A H 0.249996 0.220929 0.093241 0.023 Uiso 1 1 calc R U . . .
H4B H 0.268345 0.407880 0.075443 0.023 Uiso 1 1 calc R U . . .
C5 C 0.23420(15) 0.37626(19) 0.16756(7) 0.0216(3) Uani 1 1 d . . . . .
H5A H 0.142273 0.410952 0.157834 0.026 Uiso 1 1 calc R U . . .
H5B H 0.234806 0.282082 0.196080 0.026 Uiso 1 1 calc R U . . .
C6 C 0.31199(14) 0.51497(18) 0.19957(7) 0.0177(3) Uani 1 1 d . . . . .
H6A H 0.258994 0.566690 0.230088 0.021 Uiso 1 1 calc R U . . .
H6B H 0.392026 0.470505 0.222546 0.021 Uiso 1 1 calc R U . . .
C7 C 0.51457(15) 0.3550(2) 0.06407(7) 0.0212(3) Uani 1 1 d . . . . .
H7A H 0.465651 0.401119 0.026507 0.025 Uiso 1 1 calc R U . . .
H7B H 0.591886 0.289099 0.056090 0.025 Uiso 1 1 calc R U . . .
C8 C 0.64948(14) 0.45102(18) 0.16381(7) 0.0180(3) Uani 1 1 d . . . . .
C9 C 0.76539(15) 0.5167(2) 0.14491(8) 0.0226(3) Uani 1 1 d . . . . .
C10 C 0.88103(16) 0.5177(2) 0.18369(9) 0.0310(4) Uani 1 1 d . . . . .
H10 H 0.957532 0.565913 0.170226 0.037 Uiso 1 1 calc R U . . .
C11 C 0.88429(17) 0.4480(2) 0.24199(10) 0.0350(4) Uani 1 1 d . . . . .
H11 H 0.963144 0.448383 0.268705 0.042 Uiso 1 1 calc R U . . .
C12 C 0.77277(18) 0.3779(2) 0.26141(9) 0.0322(4) Uani 1 1 d . . . . .
H12 H 0.775293 0.328011 0.301115 0.039 Uiso 1 1 calc R U . . .
C13 C 0.65678(16) 0.3805(2) 0.22262(8) 0.0244(3) Uani 1 1 d . . . . .
H13 H 0.580518 0.332894 0.236605 0.029 Uiso 1 1 calc R U . . .
C14 C 0.21514(14) 0.83087(18) 0.06546(6) 0.0158(3) Uani 1 1 d . . . . .
C15 C 0.28442(15) 0.93571(18) 0.03018(7) 0.0187(3) Uani 1 1 d . . . . .
H15 H 0.360736 0.989294 0.048128 0.022 Uiso 1 1 calc R U . . .
C16 C 0.24030(16) 0.9608(2) -0.03162(7) 0.0226(3) Uani 1 1 d . . . . .
H16 H 0.286722 1.032846 -0.055931 0.027 Uiso 1 1 calc R U . . .
C17 C 0.12875(16) 0.8819(2) -0.05881(7) 0.0244(3) Uani 1 1 d . . . . .
C18 C 0.06243(16) 0.7766(2) -0.02242(8) 0.0272(4) Uani 1 1 d . . . . .
H18 H -0.013054 0.721397 -0.040448 0.033 Uiso 1 1 calc R U . . .
C19 C 0.10410(15) 0.7504(2) 0.03957(7) 0.0222(3) Uani 1 1 d . . . . .
H19 H 0.057581 0.678590 0.063976 0.027 Uiso 1 1 calc R U . . .
C20 C 0.0818(2) 0.9117(3) -0.12600(8) 0.0366(4) Uani 1 1 d . . . . .
H20A H 0.145600 0.867690 -0.152538 0.055 Uiso 1 1 calc R U . . .
H20B H 0.072007 1.028854 -0.133267 0.055 Uiso 1 1 calc R U . . .
H20C H -0.002746 0.857925 -0.135852 0.055 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C9 1.7440(17) . ?
S1 O2 1.4309(11) . ?
S1 O3 1.4369(11) . ?
S1 N1 1.6810(12) . ?
S1 C14 1.7592(14) . ?
O1 C1 1.2126(18) . ?
N1 C1 1.4012(18) . ?
N1 C6 1.4856(18) . ?
C1 C2 1.5189(19) . ?
C2 C8 1.5072(19) . ?
C2 C3 1.515(2) . ?
C2 C7 1.515(2) . ?
C3 C7 1.502(2) . ?
C3 C4 1.515(2) . ?
C3 H3 1.0000 . ?
C4 C5 1.524(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.522(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C13 1.394(2) . ?
C8 C9 1.403(2) . ?
C9 C10 1.389(2) . ?
C10 C11 1.383(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.382(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.392(2) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C19 1.391(2) . ?
C14 C15 1.391(2) . ?
C15 C16 1.386(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.398(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.391(3) . ?
C17 C20 1.508(2) . ?
C18 C19 1.386(2) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 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
O2 S1 O3 118.33(7) . . ?
O2 S1 N1 109.94(6) . . ?
O3 S1 N1 104.16(6) . . ?
O2 S1 C14 108.67(7) . . ?
O3 S1 C14 108.39(7) . . ?
N1 S1 C14 106.74(6) . . ?
C1 N1 C6 122.48(12) . . ?
C1 N1 S1 118.79(10) . . ?
C6 N1 S1 118.73(9) . . ?
O1 C1 N1 120.28(13) . . ?
O1 C1 C2 123.36(13) . . ?
N1 C1 C2 116.37(12) . . ?
C8 C2 C3 119.55(12) . . ?
C8 C2 C7 116.99(12) . . ?
C3 C2 C7 59.44(10) . . ?
C8 C2 C1 113.47(12) . . ?
C3 C2 C1 119.21(11) . . ?
C7 C2 C1 117.86(12) . . ?
C7 C3 C2 60.29(10) . . ?
C7 C3 C4 117.54(13) . . ?
C2 C3 C4 118.34(12) . . ?
C7 C3 H3 116.3 . . ?
C2 C3 H3 116.3 . . ?
C4 C3 H3 116.3 . . ?
C3 C4 C5 112.30(12) . . ?
C3 C4 H4A 109.1 . . ?
C5 C4 H4A 109.1 . . ?
C3 C4 H4B 109.1 . . ?
C5 C4 H4B 109.1 . . ?
H4A C4 H4B 107.9 . . ?
C6 C5 C4 111.63(12) . . ?
C6 C5 H5A 109.3 . . ?
C4 C5 H5A 109.3 . . ?
C6 C5 H5B 109.3 . . ?
C4 C5 H5B 109.3 . . ?
H5A C5 H5B 108.0 . . ?
N1 C6 C5 112.41(12) . . ?
N1 C6 H6A 109.1 . . ?
C5 C6 H6A 109.1 . . ?
N1 C6 H6B 109.1 . . ?
C5 C6 H6B 109.1 . . ?
H6A C6 H6B 107.9 . . ?
C3 C7 C2 60.27(9) . . ?
C3 C7 H7A 117.7 . . ?
C2 C7 H7A 117.7 . . ?
C3 C7 H7B 117.7 . . ?
C2 C7 H7B 117.7 . . ?
H7A C7 H7B 114.9 . . ?
C13 C8 C9 116.84(14) . . ?
C13 C8 C2 120.86(13) . . ?
C9 C8 C2 122.30(14) . . ?
C10 C9 C8 121.84(16) . . ?
C10 C9 Cl1 116.92(13) . . ?
C8 C9 Cl1 121.24(12) . . ?
C11 C10 C9 119.68(16) . . ?
C11 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
C12 C11 C10 119.99(15) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C12 C13 119.82(17) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
C12 C13 C8 121.79(16) . . ?
C12 C13 H13 119.1 . . ?
C8 C13 H13 119.1 . . ?
C19 C14 C15 121.12(14) . . ?
C19 C14 S1 118.46(12) . . ?
C15 C14 S1 120.22(11) . . ?
C16 C15 C14 118.91(14) . . ?
C16 C15 H15 120.5 . . ?
C14 C15 H15 120.5 . . ?
C15 C16 C17 121.21(15) . . ?
C15 C16 H16 119.4 . . ?
C17 C16 H16 119.4 . . ?
C18 C17 C16 118.46(14) . . ?
C18 C17 C20 121.15(16) . . ?
C16 C17 C20 120.39(16) . . ?
C19 C18 C17 121.41(15) . . ?
C19 C18 H18 119.3 . . ?
C17 C18 H18 119.3 . . ?
C18 C19 C14 118.89(15) . . ?
C18 C19 H19 120.6 . . ?
C14 C19 H19 120.6 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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
O2 S1 N1 C1 -65.44(12) . . . . ?
O3 S1 N1 C1 166.81(10) . . . . ?
C14 S1 N1 C1 52.25(12) . . . . ?
O2 S1 N1 C6 114.94(11) . . . . ?
O3 S1 N1 C6 -12.81(12) . . . . ?
C14 S1 N1 C6 -127.37(11) . . . . ?
C6 N1 C1 O1 -171.34(13) . . . . ?
S1 N1 C1 O1 9.05(18) . . . . ?
C6 N1 C1 C2 8.80(19) . . . . ?
S1 N1 C1 C2 -170.81(9) . . . . ?
O1 C1 C2 C8 76.35(18) . . . . ?
N1 C1 C2 C8 -103.79(14) . . . . ?
O1 C1 C2 C3 -134.46(15) . . . . ?
N1 C1 C2 C3 45.39(17) . . . . ?
O1 C1 C2 C7 -65.77(19) . . . . ?
N1 C1 C2 C7 114.09(14) . . . . ?
C8 C2 C3 C7 -105.73(15) . . . . ?
C1 C2 C3 C7 106.96(14) . . . . ?
C8 C2 C3 C4 146.98(14) . . . . ?
C7 C2 C3 C4 -107.29(15) . . . . ?
C1 C2 C3 C4 -0.33(19) . . . . ?
C7 C3 C4 C5 -143.13(14) . . . . ?
C2 C3 C4 C5 -73.85(17) . . . . ?
C3 C4 C5 C6 46.95(17) . . . . ?
C1 N1 C6 C5 -80.74(16) . . . . ?
S1 N1 C6 C5 98.86(13) . . . . ?
C4 C5 C6 N1 41.78(17) . . . . ?
C4 C3 C7 C2 108.59(14) . . . . ?
C8 C2 C7 C3 110.00(14) . . . . ?
C1 C2 C7 C3 -109.20(14) . . . . ?
C3 C2 C8 C13 -44.9(2) . . . . ?
C7 C2 C8 C13 -113.40(16) . . . . ?
C1 C2 C8 C13 104.13(16) . . . . ?
C3 C2 C8 C9 134.99(15) . . . . ?
C7 C2 C8 C9 66.53(19) . . . . ?
C1 C2 C8 C9 -75.94(18) . . . . ?
C13 C8 C9 C10 -2.5(2) . . . . ?
C2 C8 C9 C10 177.55(15) . . . . ?
C13 C8 C9 Cl1 176.85(12) . . . . ?
C2 C8 C9 Cl1 -3.1(2) . . . . ?
C8 C9 C10 C11 1.9(3) . . . . ?
Cl1 C9 C10 C11 -177.45(14) . . . . ?
C9 C10 C11 C12 0.0(3) . . . . ?
C10 C11 C12 C13 -1.3(3) . . . . ?
C11 C12 C13 C8 0.6(3) . . . . ?
C9 C8 C13 C12 1.2(2) . . . . ?
C2 C8 C13 C12 -178.85(15) . . . . ?
O2 S1 C14 C19 -155.69(12) . . . . ?
O3 S1 C14 C19 -25.88(14) . . . . ?
N1 S1 C14 C19 85.79(13) . . . . ?
O2 S1 C14 C15 19.33(14) . . . . ?
O3 S1 C14 C15 149.14(12) . . . . ?
N1 S1 C14 C15 -99.19(13) . . . . ?
C19 C14 C15 C16 0.7(2) . . . . ?
S1 C14 C15 C16 -174.19(11) . . . . ?
C14 C15 C16 C17 -0.5(2) . . . . ?
C15 C16 C17 C18 -0.1(2) . . . . ?
C15 C16 C17 C20 179.56(15) . . . . ?
C16 C17 C18 C19 0.6(3) . . . . ?
C20 C17 C18 C19 -179.11(16) . . . . ?
C17 C18 C19 C14 -0.4(3) . . . . ?
C15 C14 C19 C18 -0.3(2) . . . . ?
S1 C14 C19 C18 174.70(13) . . . . ?

_refine_diff_density_max         0.394
_refine_diff_density_min         -0.421
_refine_diff_density_rms         0.050

####################################################################### 
# 
# 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_YMD_58F_0m
_audit_block_doi                 10.5517/ccdc.csd.cc278tt5
_database_code_depnum_ccdc_archive 'CCDC 2064067'
loop_
_audit_author_name
_audit_author_address
'Matthias Zeller'
;Purdue University, Department of Chemistry
United States of America
;
_audit_update_record             
;
2021-02-20 deposited with the CCDC.	2021-05-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H18 Cl N O3 S'
_chemical_formula_weight         375.85

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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.6716(2)
_cell_length_b                   13.8410(6)
_cell_length_c                   22.4239(9)
_cell_angle_alpha                86.8683(17)
_cell_angle_beta                 89.7811(17)
_cell_angle_gamma                89.8515(18)
_cell_volume                     1757.64(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9877
_cell_measurement_theta_min      3.9486
_cell_measurement_theta_max      79.4475

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.420
_exptl_crystal_F_000             784
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    3.189
_shelx_estimated_absorpt_T_min   0.491
_shelx_estimated_absorpt_T_max   0.701
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5835
_exptl_absorpt_correction_T_max  0.7543
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'I-mu-S microsource X-ray tube'
_diffrn_source_current           '1.0 mA'
_diffrn_source_voltage           '50 kV'
_diffrn_radiation_monochromator  'laterally graded multilayer (Goebel) mirror'
_diffrn_measurement_device_type  
;
Bruker AXS D8 Quest diffractometer with PhotonIII_C14 charge-integrating and 
photon counting pixel array detector
;
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean 7.4074
_diffrn_reflns_number            19757
_diffrn_reflns_av_unetI/netI     0.0330
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.973
_diffrn_reflns_theta_max         79.454
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.923
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.923
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.923
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             7045
_reflns_number_gt                6233
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'Apex3 v2019.1-0 (Bruker, 2019)'
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  
;  
SHELXL-2018/3 (Sheldrick, 2015, 2018), 
SHELXLE Rev1149 (Hübschle et al., 2011)
;
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
The structure exhibits pseudo-monoclinic symmetry, emulating the 
space group P2(1)/c. Exact monoclinic symmetry is broken by deviations 
of unit cell angles from 90 degrees (89.7811(17) and 89.8515(18)), by 
slight modulation of atom positions and ADPs, by disorder only present 
for one of the two molecules, and by a pseudo-merohedric twinning 
Flack parameter deviating from one half (0.286(5), twin transformation 
matrix 1 0 0, 0.014 -1 0, 0.028 0 -1). 

The cyclopropane moiety and surrounding atoms differ for the two 
molecules related by pseudosymmetry. For molecule B, the cyclopropane 
ring is located on opposing sides of the molecule plane, inducing 
disorder for the six membered ring. Disorder modelling was extended 
to the chlorobenzene substituent. The two disordered moieties were
restrained to have similar geometries (SAME and SADI commands of 
SHELXL). Uij components of ADPs for disordered atoms of the six and 
three membered rings closer to each other than 2.0 Angstrom were 
restrained to be similar (SIMU command of SHELXL). ADPs of equivalent 
atoms in the chlorobenzene substituent were constrained to be 
identical. Subject to these conditions the occupancy ratio refined 
to 0.845(5) to 0.155(5). 

For molecule A, no static disorder is observed, but the 
cyclopropane C atoms exhibit elongated ADPs, indicating pronounced 
libration. No disorder was refined for this moiety.  
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0172P)²+1.6683P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7045
_refine_ls_number_parameters     521
_refine_ls_number_restraints     221
_refine_ls_R_factor_all          0.0482
_refine_ls_R_factor_gt           0.0425
_refine_ls_wR_factor_ref         0.0978
_refine_ls_wR_factor_gt          0.0948
_refine_ls_goodness_of_fit_ref   1.135
_refine_ls_restrained_S_all      1.125
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1A Cl -0.27691(17) 0.93959(6) 0.03363(4) 0.0348(2) Uani 1 1 d . . . . .
S1A S 0.61546(17) 0.60608(6) 0.32269(4) 0.0320(2) Uani 1 1 d . . . . .
O1A O 0.4129(4) 0.73260(15) 0.23465(10) 0.0278(5) Uani 1 1 d . . . . .
O2A O 0.8257(5) 0.6467(2) 0.29635(11) 0.0391(6) Uani 1 1 d . . . . .
O3A O 0.6357(6) 0.51988(19) 0.36074(11) 0.0450(7) Uani 1 1 d . . . . .
N1A N 0.4303(6) 0.57608(19) 0.26869(12) 0.0298(6) Uani 1 1 d . . . . .
C1A C 0.3664(6) 0.6486(2) 0.22646(13) 0.0230(6) Uani 1 1 d . . . . .
C2A C 0.2424(6) 0.6203(2) 0.17194(13) 0.0240(6) Uani 1 1 d . . . . .
C3A C 0.1318(9) 0.5196(2) 0.17451(19) 0.0452(10) Uani 1 1 d . . . . .
H3A H -0.015720 0.513629 0.150733 0.054 Uiso 1 1 calc R U . . .
C4A C 0.1357(9) 0.4628(2) 0.2334(2) 0.0479(11) Uani 1 1 d . . . . .
H4AA H 0.106403 0.393725 0.226735 0.058 Uiso 1 1 calc R U . . .
H4AB H 0.006976 0.485826 0.259025 0.058 Uiso 1 1 calc R U . . .
C5A C 0.3673(8) 0.4718(2) 0.26544(17) 0.0387(9) Uani 1 1 d . . . . .
H5AA H 0.354644 0.441266 0.306283 0.046 Uiso 1 1 calc R U . . .
H5AB H 0.492500 0.437854 0.243856 0.046 Uiso 1 1 calc R U . . .
C6A C 0.3520(9) 0.5389(3) 0.13860(16) 0.0495(12) Uani 1 1 d . . . . .
H6AA H 0.338260 0.542071 0.094536 0.059 Uiso 1 1 calc R U . . .
H6AB H 0.501151 0.510383 0.154255 0.059 Uiso 1 1 calc R U . . .
C7A C 0.1204(6) 0.7010(2) 0.13706(13) 0.0230(6) Uani 1 1 d . . . . .
C8A C -0.0936(7) 0.7374(2) 0.15828(15) 0.0300(7) Uani 1 1 d . . . . .
H8A H -0.156520 0.711564 0.195101 0.036 Uiso 1 1 calc R U . . .
C9A C -0.2136(7) 0.8096(2) 0.12669(15) 0.0301(7) Uani 1 1 d . . . . .
H9A H -0.359025 0.833067 0.141396 0.036 Uiso 1 1 calc R U . . .
C10A C -0.1216(6) 0.8479(2) 0.07341(14) 0.0251(7) Uani 1 1 d . . . . .
C11A C 0.0904(6) 0.8150(2) 0.05135(14) 0.0277(7) Uani 1 1 d . . . . .
H11A H 0.152851 0.842206 0.014830 0.033 Uiso 1 1 calc R U . . .
C12A C 0.2100(6) 0.7420(2) 0.08322(13) 0.0258(7) Uani 1 1 d . . . . .
H12A H 0.355767 0.719229 0.068284 0.031 Uiso 1 1 calc R U . . .
C13A C 0.4691(7) 0.6945(3) 0.36245(13) 0.0289(7) Uani 1 1 d . . . . .
C14A C 0.5770(7) 0.7838(3) 0.36759(15) 0.0323(8) Uani 1 1 d . . . . .
H14A H 0.718271 0.799602 0.346390 0.039 Uiso 1 1 calc R U . . .
C15A C 0.4734(8) 0.8490(3) 0.40437(15) 0.0367(9) Uani 1 1 d . . . . .
H15A H 0.546631 0.909828 0.408642 0.044 Uiso 1 1 calc R U . . .
C16A C 0.2650(7) 0.8278(3) 0.43527(14) 0.0337(8) Uani 1 1 d . . . . .
C17A C 0.1580(7) 0.7382(3) 0.42818(15) 0.0365(8) Uani 1 1 d . . . . .
H17A H 0.013825 0.722959 0.448203 0.044 Uiso 1 1 calc R U . . .
C18A C 0.2611(7) 0.6715(3) 0.39212(15) 0.0327(8) Uani 1 1 d . . . . .
H18A H 0.189184 0.610351 0.387850 0.039 Uiso 1 1 calc R U . . .
C19A C 0.1542(9) 0.8985(3) 0.47557(17) 0.0479(11) Uani 1 1 d . . . . .
H19A H 0.065741 0.947385 0.451506 0.072 Uiso 1 1 calc R U . . .
H19B H 0.277721 0.930269 0.497815 0.072 Uiso 1 1 calc R U . . .
H19C H 0.046948 0.864093 0.503671 0.072 Uiso 1 1 calc R U . . .
S1B S -0.11101(18) 0.10616(6) 0.32392(4) 0.0324(2) Uani 1 1 d . . . . .
O1B O 0.0930(5) 0.23111(16) 0.23595(10) 0.0345(6) Uani 1 1 d . . . . .
O2B O -0.3199(5) 0.14753(19) 0.29845(11) 0.0387(6) Uani 1 1 d . . . . .
O3B O -0.1338(6) 0.02030(19) 0.36255(11) 0.0488(8) Uani 1 1 d . . . . .
N1B N 0.0743(6) 0.07400(19) 0.26988(12) 0.0302(6) Uani 1 1 d D U . . .
C1B C 0.1457(7) 0.1477(2) 0.22795(14) 0.0291(7) Uani 1 1 d D U . . .
C2B C 0.2693(10) 0.1196(3) 0.1729(2) 0.0343(12) Uani 0.845(5) 1 d D U P A 1
C3B C 0.3756(12) 0.0199(3) 0.1747(2) 0.0446(12) Uani 0.845(5) 1 d D U P A 1
H3B H 0.523262 0.013477 0.150662 0.054 Uiso 0.845(5) 1 calc R U P A 1
C4B C 0.3721(11) -0.0372(3) 0.2342(2) 0.0479(12) Uani 0.845(5) 1 d D U P A 1
H4BA H 0.404484 -0.106134 0.227641 0.057 Uiso 0.845(5) 1 calc R U P A 1
H4BB H 0.499296 -0.013412 0.259696 0.057 Uiso 0.845(5) 1 calc R U P A 1
C5B C 0.1408(12) -0.0293(3) 0.2663(2) 0.0400(13) Uani 0.845(5) 1 d D U P A 1
H5BA H 0.017155 -0.063674 0.244786 0.048 Uiso 0.845(5) 1 calc R U P A 1
H5BB H 0.153807 -0.060102 0.307102 0.048 Uiso 0.845(5) 1 calc R U P A 1
C6B C 0.1609(12) 0.0363(3) 0.1399(2) 0.0472(12) Uani 0.845(5) 1 d D U P A 1
H6BA H 0.012833 0.007423 0.156041 0.057 Uiso 0.845(5) 1 calc R U P A 1
H6BB H 0.174864 0.038697 0.095811 0.057 Uiso 0.845(5) 1 calc R U P A 1
C7B C 0.3882(12) 0.2020(3) 0.1379(2) 0.0293(11) Uani 0.845(5) 1 d D . P A 1
C8B C 0.5935(11) 0.2389(4) 0.1601(3) 0.0298(13) Uani 0.845(5) 1 d D . P A 1
H8B H 0.651920 0.214262 0.197541 0.036 Uiso 0.845(5) 1 calc R U P A 1
C9B C 0.7163(14) 0.3119(6) 0.1281(3) 0.0281(13) Uani 0.845(5) 1 d D . P A 1
H9B H 0.858624 0.336952 0.143239 0.034 Uiso 0.845(5) 1 calc R U P A 1
C10B C 0.6263(15) 0.3471(6) 0.0739(4) 0.0251(8) Uani 0.845(5) 1 d D . P A 1
C11B C 0.4171(13) 0.3134(7) 0.0515(3) 0.0295(11) Uani 0.845(5) 1 d D . P A 1
H11B H 0.354293 0.340030 0.014910 0.035 Uiso 0.845(5) 1 calc R U P A 1
C12B C 0.3010(14) 0.2390(6) 0.0843(3) 0.0323(11) Uani 0.845(5) 1 d D . P A 1
H12B H 0.159105 0.213496 0.069215 0.039 Uiso 0.845(5) 1 calc R U P A 1
Cl1B Cl 0.7807(4) 0.4383(2) 0.03370(14) 0.0323(4) Uani 0.845(5) 1 d D . P A 1
C13B C 0.0343(7) 0.1946(2) 0.36349(13) 0.0279(7) Uani 1 1 d . . . . .
C14B C -0.0705(7) 0.2837(3) 0.36839(15) 0.0340(8) Uani 1 1 d . . . . .
H14B H -0.211343 0.299738 0.347243 0.041 Uiso 1 1 calc R U . . .
C15B C 0.0325(7) 0.3499(3) 0.40468(15) 0.0345(8) Uani 1 1 d . . . . .
H15B H -0.039014 0.411401 0.408607 0.041 Uiso 1 1 calc R U . . .
C16B C 0.2384(7) 0.3269(3) 0.43511(14) 0.0326(8) Uani 1 1 d . . . . .
C17B C 0.3412(7) 0.2383(3) 0.42810(16) 0.0362(8) Uani 1 1 d . . . . .
H17B H 0.484705 0.223262 0.448286 0.043 Uiso 1 1 calc R U . . .
C18B C 0.2435(7) 0.1703(3) 0.39276(15) 0.0343(8) Uani 1 1 d . . . . .
H18B H 0.316655 0.109170 0.388614 0.041 Uiso 1 1 calc R U . . .
C19B C 0.3464(9) 0.3994(3) 0.47493(16) 0.0463(10) Uani 1 1 d . . . . .
H19D H 0.511842 0.409878 0.463676 0.069 Uiso 1 1 calc R U . . .
H19E H 0.337204 0.374520 0.516639 0.069 Uiso 1 1 calc R U . . .
H19F H 0.260118 0.460768 0.470303 0.069 Uiso 1 1 calc R U . . .
C2D C 0.324(4) 0.1120(12) 0.1834(10) 0.038(2) Uani 0.155(5) 1 d D U P A 2
C3D C 0.288(5) 0.0141(15) 0.1585(10) 0.040(2) Uani 0.155(5) 1 d D U P A 2
H3D H 0.303772 0.009393 0.114329 0.048 Uiso 0.155(5) 1 calc R U P A 2
C4D C 0.103(4) -0.0478(13) 0.1907(8) 0.044(2) Uani 0.155(5) 1 d D U P A 2
H4DA H -0.052902 -0.033208 0.172658 0.052 Uiso 0.155(5) 1 calc R U P A 2
H4DB H 0.138673 -0.116863 0.185325 0.052 Uiso 0.155(5) 1 calc R U P A 2
C5D C 0.092(7) -0.0311(13) 0.2563(10) 0.039(3) Uani 0.155(5) 1 d D U P A 2
H5DA H 0.235376 -0.058971 0.275717 0.047 Uiso 0.155(5) 1 calc R U P A 2
H5DB H -0.045809 -0.065837 0.273960 0.047 Uiso 0.155(5) 1 calc R U P A 2
C6D C 0.507(4) 0.0277(13) 0.1929(10) 0.042(3) Uani 0.155(5) 1 d D U P A 2
H6DA H 0.657281 0.032886 0.170612 0.051 Uiso 0.155(5) 1 calc R U P A 2
H6DB H 0.517501 -0.004908 0.233252 0.051 Uiso 0.155(5) 1 calc R U P A 2
C7D C 0.418(6) 0.1946(13) 0.1428(12) 0.0293(11) Uani 0.155(5) 1 d D . P A 2
C8D C 0.636(6) 0.231(3) 0.1557(17) 0.0298(13) Uani 0.155(5) 1 d D . P A 2
H8D H 0.720666 0.203943 0.189066 0.036 Uiso 0.155(5) 1 calc R U P A 2
C9D C 0.736(8) 0.307(3) 0.1213(19) 0.0281(13) Uani 0.155(5) 1 d D . P A 2
H9D H 0.884484 0.332955 0.131198 0.034 Uiso 0.155(5) 1 calc R U P A 2
C10D C 0.611(8) 0.344(3) 0.072(2) 0.0251(8) Uani 0.155(5) 1 d D . P A 2
C11D C 0.391(8) 0.309(4) 0.058(2) 0.0295(11) Uani 0.155(5) 1 d D . P A 2
H11D H 0.305343 0.336343 0.025244 0.035 Uiso 0.155(5) 1 calc R U P A 2
C12D C 0.298(8) 0.234(3) 0.0945(18) 0.0323(11) Uani 0.155(5) 1 d D . P A 2
H12D H 0.147774 0.208455 0.085368 0.039 Uiso 0.155(5) 1 calc R U P A 2
Cl1D Cl 0.737(3) 0.4395(14) 0.0287(9) 0.0323(4) Uani 0.155(5) 1 d D . P A 2


_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
Cl1A C10A 1.749(3) . ?
S1A O2A 1.432(3) . ?
S1A O3A 1.433(2) . ?
S1A N1A 1.676(3) . ?
S1A C13A 1.758(4) . ?
O1A C1A 1.217(4) . ?
N1A C1A 1.390(4) . ?
N1A C5A 1.493(4) . ?
C1A C2A 1.484(4) . ?
C2A C7A 1.497(4) . ?
C2A C6A 1.517(4) . ?
C2A C3A 1.528(5) . ?
C3A C6A 1.500(7) . ?
C3A C4A 1.501(5) . ?
C3A H3A 1.0000 . ?
C4A C5A 1.508(6) . ?
C4A H4AA 0.9900 . ?
C4A H4AB 0.9900 . ?
C5A H5AA 0.9900 . ?
C5A H5AB 0.9900 . ?
C6A H6AA 0.9900 . ?
C6A H6AB 0.9900 . ?
C7A C12A 1.400(4) . ?
C7A C8A 1.404(5) . ?
C8A C9A 1.374(5) . ?
C8A H8A 0.9500 . ?
C9A C10A 1.381(5) . ?
C9A H9A 0.9500 . ?
C10A C11A 1.384(5) . ?
C11A C12A 1.384(5) . ?
C11A H11A 0.9500 . ?
C12A H12A 0.9500 . ?
C13A C18A 1.382(5) . ?
C13A C14A 1.391(5) . ?
C14A C15A 1.383(5) . ?
C14A H14A 0.9500 . ?
C15A C16A 1.391(6) . ?
C15A H15A 0.9500 . ?
C16A C17A 1.400(5) . ?
C16A C19A 1.503(5) . ?
C17A C18A 1.387(5) . ?
C17A H17A 0.9500 . ?
C18A H18A 0.9500 . ?
C19A H19A 0.9800 . ?
C19A H19B 0.9800 . ?
C19A H19C 0.9800 . ?
S1B O2B 1.423(3) . ?
S1B O3B 1.438(2) . ?
S1B N1B 1.679(3) . ?
S1B C13B 1.759(3) . ?
O1B C1B 1.215(4) . ?
N1B C1B 1.408(4) . ?
N1B C5B 1.485(5) . ?
N1B C5D 1.505(17) . ?
C1B C2B 1.487(5) . ?
C1B C2D 1.518(16) . ?
C2B C3B 1.504(6) . ?
C2B C7B 1.508(5) . ?
C2B C6B 1.535(6) . ?
C3B C6B 1.459(9) . ?
C3B C4B 1.515(6) . ?
C3B H3B 1.0000 . ?
C4B C5B 1.501(8) . ?
C4B H4BA 0.9900 . ?
C4B H4BB 0.9900 . ?
C5B H5BA 0.9900 . ?
C5B H5BB 0.9900 . ?
C6B H6BA 0.9900 . ?
C6B H6BB 0.9900 . ?
C7B C12B 1.374(6) . ?
C7B C8B 1.378(6) . ?
C8B C9B 1.393(5) . ?
C8B H8B 0.9500 . ?
C9B C10B 1.385(5) . ?
C9B H9B 0.9500 . ?
C10B C11B 1.382(6) . ?
C10B Cl1B 1.745(4) . ?
C11B C12B 1.398(6) . ?
C11B H11B 0.9500 . ?
C12B H12B 0.9500 . ?
C13B C14B 1.377(5) . ?
C13B C18B 1.390(5) . ?
C14B C15B 1.390(5) . ?
C14B H14B 0.9500 . ?
C15B C16B 1.382(6) . ?
C15B H15B 0.9500 . ?
C16B C17B 1.373(5) . ?
C16B C19B 1.511(5) . ?
C17B C18B 1.382(5) . ?
C17B H17B 0.9500 . ?
C18B H18B 0.9500 . ?
C19B H19D 0.9800 . ?
C19B H19E 0.9800 . ?
C19B H19F 0.9800 . ?
C2D C3D 1.506(17) . ?
C2D C7D 1.520(15) . ?
C2D C6D 1.566(18) . ?
C3D C6D 1.48(2) . ?
C3D C4D 1.514(17) . ?
C3D H3D 1.0000 . ?
C4D C5D 1.503(18) . ?
C4D H4DA 0.9900 . ?
C4D H4DB 0.9900 . ?
C5D H5DA 0.9900 . ?
C5D H5DB 0.9900 . ?
C6D H6DA 0.9900 . ?
C6D H6DB 0.9900 . ?
C7D C12D 1.365(17) . ?
C7D C8D 1.375(17) . ?
C8D C9D 1.390(17) . ?
C8D H8D 0.9500 . ?
C9D C10D 1.387(17) . ?
C9D H9D 0.9500 . ?
C10D C11D 1.380(17) . ?
C10D Cl1D 1.746(16) . ?
C11D C12D 1.393(17) . ?
C11D H11D 0.9500 . ?
C12D H12D 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2A S1A O3A 118.32(18) . . ?
O2A S1A N1A 109.49(15) . . ?
O3A S1A N1A 104.46(16) . . ?
O2A S1A C13A 109.29(17) . . ?
O3A S1A C13A 108.42(16) . . ?
N1A S1A C13A 106.15(16) . . ?
C1A N1A C5A 124.5(3) . . ?
C1A N1A S1A 117.3(2) . . ?
C5A N1A S1A 117.8(2) . . ?
O1A C1A N1A 120.0(3) . . ?
O1A C1A C2A 121.7(3) . . ?
N1A C1A C2A 118.3(3) . . ?
C1A C2A C7A 115.4(3) . . ?
C1A C2A C6A 116.6(3) . . ?
C7A C2A C6A 118.9(3) . . ?
C1A C2A C3A 116.5(3) . . ?
C7A C2A C3A 118.8(3) . . ?
C6A C2A C3A 59.0(3) . . ?
C6A C3A C4A 121.9(4) . . ?
C6A C3A C2A 60.1(3) . . ?
C4A C3A C2A 117.4(3) . . ?
C6A C3A H3A 115.4 . . ?
C4A C3A H3A 115.4 . . ?
C2A C3A H3A 115.4 . . ?
C3A C4A C5A 112.4(4) . . ?
C3A C4A H4AA 109.1 . . ?
C5A C4A H4AA 109.1 . . ?
C3A C4A H4AB 109.1 . . ?
C5A C4A H4AB 109.1 . . ?
H4AA C4A H4AB 107.9 . . ?
N1A C5A C4A 109.9(3) . . ?
N1A C5A H5AA 109.7 . . ?
C4A C5A H5AA 109.7 . . ?
N1A C5A H5AB 109.7 . . ?
C4A C5A H5AB 109.7 . . ?
H5AA C5A H5AB 108.2 . . ?
C3A C6A C2A 60.9(2) . . ?
C3A C6A H6AA 117.7 . . ?
C2A C6A H6AA 117.7 . . ?
C3A C6A H6AB 117.7 . . ?
C2A C6A H6AB 117.7 . . ?
H6AA C6A H6AB 114.8 . . ?
C12A C7A C8A 117.9(3) . . ?
C12A C7A C2A 122.6(3) . . ?
C8A C7A C2A 119.5(3) . . ?
C9A C8A C7A 121.1(3) . . ?
C9A C8A H8A 119.4 . . ?
C7A C8A H8A 119.4 . . ?
C8A C9A C10A 119.6(3) . . ?
C8A C9A H9A 120.2 . . ?
C10A C9A H9A 120.2 . . ?
C9A C10A C11A 121.1(3) . . ?
C9A C10A Cl1A 119.0(3) . . ?
C11A C10A Cl1A 119.9(2) . . ?
C10A C11A C12A 119.1(3) . . ?
C10A C11A H11A 120.5 . . ?
C12A C11A H11A 120.5 . . ?
C11A C12A C7A 121.2(3) . . ?
C11A C12A H12A 119.4 . . ?
C7A C12A H12A 119.4 . . ?
C18A C13A C14A 121.3(3) . . ?
C18A C13A S1A 119.7(3) . . ?
C14A C13A S1A 118.7(3) . . ?
C15A C14A C13A 118.3(4) . . ?
C15A C14A H14A 120.8 . . ?
C13A C14A H14A 120.8 . . ?
C14A C15A C16A 121.9(4) . . ?
C14A C15A H15A 119.1 . . ?
C16A C15A H15A 119.1 . . ?
C15A C16A C17A 118.5(3) . . ?
C15A C16A C19A 121.7(4) . . ?
C17A C16A C19A 119.9(4) . . ?
C18A C17A C16A 120.4(4) . . ?
C18A C17A H17A 119.8 . . ?
C16A C17A H17A 119.8 . . ?
C13A C18A C17A 119.6(3) . . ?
C13A C18A H18A 120.2 . . ?
C17A C18A H18A 120.2 . . ?
C16A C19A H19A 109.5 . . ?
C16A C19A H19B 109.5 . . ?
H19A C19A H19B 109.5 . . ?
C16A C19A H19C 109.5 . . ?
H19A C19A H19C 109.5 . . ?
H19B C19A H19C 109.5 . . ?
O2B S1B O3B 117.93(19) . . ?
O2B S1B N1B 110.23(15) . . ?
O3B S1B N1B 104.34(17) . . ?
O2B S1B C13B 108.66(17) . . ?
O3B S1B C13B 108.28(16) . . ?
N1B S1B C13B 106.83(16) . . ?
C1B N1B C5B 123.8(3) . . ?
C1B N1B C5D 121.3(10) . . ?
C1B N1B S1B 116.7(2) . . ?
C5B N1B S1B 119.3(3) . . ?
C5D N1B S1B 118.9(12) . . ?
O1B C1B N1B 119.4(3) . . ?
O1B C1B C2B 122.0(3) . . ?
N1B C1B C2B 118.4(3) . . ?
O1B C1B C2D 127.2(7) . . ?
N1B C1B C2D 112.3(8) . . ?
C1B C2B C3B 116.5(4) . . ?
C1B C2B C7B 114.6(3) . . ?
C3B C2B C7B 120.2(4) . . ?
C1B C2B C6B 116.6(4) . . ?
C3B C2B C6B 57.4(4) . . ?
C7B C2B C6B 119.8(4) . . ?
C6B C3B C2B 62.4(4) . . ?
C6B C3B C4B 121.4(5) . . ?
C2B C3B C4B 116.9(4) . . ?
C6B C3B H3B 115.3 . . ?
C2B C3B H3B 115.3 . . ?
C4B C3B H3B 115.3 . . ?
C5B C4B C3B 112.6(5) . . ?
C5B C4B H4BA 109.1 . . ?
C3B C4B H4BA 109.1 . . ?
C5B C4B H4BB 109.1 . . ?
C3B C4B H4BB 109.1 . . ?
H4BA C4B H4BB 107.8 . . ?
N1B C5B C4B 109.9(4) . . ?
N1B C5B H5BA 109.7 . . ?
C4B C5B H5BA 109.7 . . ?
N1B C5B H5BB 109.7 . . ?
C4B C5B H5BB 109.7 . . ?
H5BA C5B H5BB 108.2 . . ?
C3B C6B C2B 60.2(3) . . ?
C3B C6B H6BA 117.7 . . ?
C2B C6B H6BA 117.7 . . ?
C3B C6B H6BB 117.7 . . ?
C2B C6B H6BB 117.7 . . ?
H6BA C6B H6BB 114.9 . . ?
C12B C7B C8B 119.7(4) . . ?
C12B C7B C2B 121.9(5) . . ?
C8B C7B C2B 118.4(4) . . ?
C7B C8B C9B 120.7(5) . . ?
C7B C8B H8B 119.6 . . ?
C9B C8B H8B 119.6 . . ?
C10B C9B C8B 118.5(5) . . ?
C10B C9B H9B 120.8 . . ?
C8B C9B H9B 120.8 . . ?
C11B C10B C9B 122.0(4) . . ?
C11B C10B Cl1B 119.5(4) . . ?
C9B C10B Cl1B 118.5(4) . . ?
C10B C11B C12B 117.9(5) . . ?
C10B C11B H11B 121.1 . . ?
C12B C11B H11B 121.1 . . ?
C7B C12B C11B 121.2(5) . . ?
C7B C12B H12B 119.4 . . ?
C11B C12B H12B 119.4 . . ?
C14B C13B C18B 121.6(3) . . ?
C14B C13B S1B 119.3(3) . . ?
C18B C13B S1B 119.0(3) . . ?
C13B C14B C15B 119.1(4) . . ?
C13B C14B H14B 120.4 . . ?
C15B C14B H14B 120.4 . . ?
C16B C15B C14B 120.4(4) . . ?
C16B C15B H15B 119.8 . . ?
C14B C15B H15B 119.8 . . ?
C17B C16B C15B 118.9(3) . . ?
C17B C16B C19B 121.4(4) . . ?
C15B C16B C19B 119.7(4) . . ?
C16B C17B C18B 122.4(4) . . ?
C16B C17B H17B 118.8 . . ?
C18B C17B H17B 118.8 . . ?
C17B C18B C13B 117.5(3) . . ?
C17B C18B H18B 121.3 . . ?
C13B C18B H18B 121.3 . . ?
C16B C19B H19D 109.5 . . ?
C16B C19B H19E 109.5 . . ?
H19D C19B H19E 109.5 . . ?
C16B C19B H19F 109.5 . . ?
H19D C19B H19F 109.5 . . ?
H19E C19B H19F 109.5 . . ?
C3D C2D C1B 119.0(16) . . ?
C3D C2D C7D 119.3(14) . . ?
C1B C2D C7D 111.5(10) . . ?
C3D C2D C6D 57.5(9) . . ?
C1B C2D C6D 127.8(17) . . ?
C7D C2D C6D 112.3(14) . . ?
C6D C3D C2D 63.3(10) . . ?
C6D C3D C4D 114.7(19) . . ?
C2D C3D C4D 114.6(16) . . ?
C6D C3D H3D 117.7 . . ?
C2D C3D H3D 117.7 . . ?
C4D C3D H3D 117.7 . . ?
C5D C4D C3D 112.2(17) . . ?
C5D C4D H4DA 109.2 . . ?
C3D C4D H4DA 109.2 . . ?
C5D C4D H4DB 109.2 . . ?
C3D C4D H4DB 109.2 . . ?
H4DA C4D H4DB 107.9 . . ?
C4D C5D N1B 113.7(16) . . ?
C4D C5D H5DA 108.8 . . ?
N1B C5D H5DA 108.8 . . ?
C4D C5D H5DB 108.8 . . ?
N1B C5D H5DB 108.8 . . ?
H5DA C5D H5DB 107.7 . . ?
C3D C6D C2D 59.2(9) . . ?
C3D C6D H6DA 117.9 . . ?
C2D C6D H6DA 117.9 . . ?
C3D C6D H6DB 117.9 . . ?
C2D C6D H6DB 117.9 . . ?
H6DA C6D H6DB 115.0 . . ?
C12D C7D C8D 118.9(17) . . ?
C12D C7D C2D 123(2) . . ?
C8D C7D C2D 118(2) . . ?
C7D C8D C9D 122(2) . . ?
C7D C8D H8D 119.2 . . ?
C9D C8D H8D 119.2 . . ?
C10D C9D C8D 118(2) . . ?
C10D C9D H9D 120.9 . . ?
C8D C9D H9D 120.9 . . ?
C11D C10D C9D 121.3(17) . . ?
C11D C10D Cl1D 121(2) . . ?
C9D C10D Cl1D 118(2) . . ?
C10D C11D C12D 118(2) . . ?
C10D C11D H11D 120.8 . . ?
C12D C11D H11D 120.8 . . ?
C7D C12D C11D 122(2) . . ?
C7D C12D H12D 119.2 . . ?
C11D C12D H12D 119.2 . . ?

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
O2A S1A N1A C1A -55.9(3) . . . . ?
O3A S1A N1A C1A 176.4(3) . . . . ?
C13A S1A N1A C1A 61.9(3) . . . . ?
O2A S1A N1A C5A 117.5(3) . . . . ?
O3A S1A N1A C5A -10.2(3) . . . . ?
C13A S1A N1A C5A -124.7(3) . . . . ?
C5A N1A C1A O1A 175.4(3) . . . . ?
S1A N1A C1A O1A -11.7(4) . . . . ?
C5A N1A C1A C2A -4.8(5) . . . . ?
S1A N1A C1A C2A 168.1(2) . . . . ?
O1A C1A C2A C7A -16.5(5) . . . . ?
N1A C1A C2A C7A 163.7(3) . . . . ?
O1A C1A C2A C6A 130.3(4) . . . . ?
N1A C1A C2A C6A -49.5(5) . . . . ?
O1A C1A C2A C3A -162.9(3) . . . . ?
N1A C1A C2A C3A 17.3(5) . . . . ?
C1A C2A C3A C6A -106.5(3) . . . . ?
C7A C2A C3A C6A 108.3(3) . . . . ?
C1A C2A C3A C4A 6.3(5) . . . . ?
C7A C2A C3A C4A -138.9(4) . . . . ?
C6A C2A C3A C4A 112.8(5) . . . . ?
C6A C3A C4A C5A 28.9(5) . . . . ?
C2A C3A C4A C5A -41.3(5) . . . . ?
C1A N1A C5A C4A -30.1(5) . . . . ?
S1A N1A C5A C4A 157.0(3) . . . . ?
C3A C4A C5A N1A 51.3(4) . . . . ?
C4A C3A C6A C2A -105.5(4) . . . . ?
C1A C2A C6A C3A 106.4(3) . . . . ?
C7A C2A C6A C3A -108.1(4) . . . . ?
C1A C2A C7A C12A 104.8(4) . . . . ?
C6A C2A C7A C12A -41.2(5) . . . . ?
C3A C2A C7A C12A -109.6(4) . . . . ?
C1A C2A C7A C8A -75.7(4) . . . . ?
C6A C2A C7A C8A 138.3(4) . . . . ?
C3A C2A C7A C8A 69.8(4) . . . . ?
C12A C7A C8A C9A 1.2(5) . . . . ?
C2A C7A C8A C9A -178.3(3) . . . . ?
C7A C8A C9A C10A -0.6(5) . . . . ?
C8A C9A C10A C11A -0.3(5) . . . . ?
C8A C9A C10A Cl1A 179.8(3) . . . . ?
C9A C10A C11A C12A 0.5(5) . . . . ?
Cl1A C10A C11A C12A -179.6(3) . . . . ?
C10A C11A C12A C7A 0.1(5) . . . . ?
C8A C7A C12A C11A -0.9(5) . . . . ?
C2A C7A C12A C11A 178.5(3) . . . . ?
O2A S1A C13A C18A -179.6(3) . . . . ?
O3A S1A C13A C18A -49.3(3) . . . . ?
N1A S1A C13A C18A 62.4(3) . . . . ?
O2A S1A C13A C14A -5.2(3) . . . . ?
O3A S1A C13A C14A 125.0(3) . . . . ?
N1A S1A C13A C14A -123.2(3) . . . . ?
C18A C13A C14A C15A 1.3(5) . . . . ?
S1A C13A C14A C15A -172.9(3) . . . . ?
C13A C14A C15A C16A -0.8(5) . . . . ?
C14A C15A C16A C17A -0.5(5) . . . . ?
C14A C15A C16A C19A 179.5(4) . . . . ?
C15A C16A C17A C18A 1.4(5) . . . . ?
C19A C16A C17A C18A -178.6(3) . . . . ?
C14A C13A C18A C17A -0.5(5) . . . . ?
S1A C13A C18A C17A 173.7(3) . . . . ?
C16A C17A C18A C13A -0.9(5) . . . . ?
O2B S1B N1B C1B 57.9(3) . . . . ?
O3B S1B N1B C1B -174.5(3) . . . . ?
C13B S1B N1B C1B -60.0(3) . . . . ?
O2B S1B N1B C5B -118.2(4) . . . . ?
O3B S1B N1B C5B 9.4(4) . . . . ?
C13B S1B N1B C5B 123.9(4) . . . . ?
O2B S1B N1B C5D -102.5(16) . . . . ?
O3B S1B N1B C5D 25.1(16) . . . . ?
C13B S1B N1B C5D 139.6(16) . . . . ?
C5B N1B C1B O1B -176.3(4) . . . . ?
C5D N1B C1B O1B 167.7(19) . . . . ?
S1B N1B C1B O1B 7.8(5) . . . . ?
C5B N1B C1B C2B 8.0(6) . . . . ?
S1B N1B C1B C2B -167.9(3) . . . . ?
C5D N1B C1B C2D -23(2) . . . . ?
S1B N1B C1B C2D 176.7(12) . . . . ?
O1B C1B C2B C3B 165.7(5) . . . . ?
N1B C1B C2B C3B -18.7(7) . . . . ?
O1B C1B C2B C7B 18.0(7) . . . . ?
N1B C1B C2B C7B -166.5(4) . . . . ?
O1B C1B C2B C6B -129.3(5) . . . . ?
N1B C1B C2B C6B 46.3(6) . . . . ?
C1B C2B C3B C6B 106.0(5) . . . . ?
C7B C2B C3B C6B -108.1(5) . . . . ?
C1B C2B C3B C4B -7.1(8) . . . . ?
C7B C2B C3B C4B 138.8(5) . . . . ?
C6B C2B C3B C4B -113.2(6) . . . . ?
C6B C3B C4B C5B -29.4(6) . . . . ?
C2B C3B C4B C5B 43.2(7) . . . . ?
C1B N1B C5B C4B 27.7(6) . . . . ?
S1B N1B C5B C4B -156.5(3) . . . . ?
C3B C4B C5B N1B -51.6(5) . . . . ?
C4B C3B C6B C2B 106.2(5) . . . . ?
C1B C2B C6B C3B -105.7(5) . . . . ?
C7B C2B C6B C3B 108.7(5) . . . . ?
C1B C2B C7B C12B -107.7(6) . . . . ?
C3B C2B C7B C12B 105.8(7) . . . . ?
C6B C2B C7B C12B 38.5(8) . . . . ?
C1B C2B C7B C8B 74.0(6) . . . . ?
C3B C2B C7B C8B -72.5(6) . . . . ?
C6B C2B C7B C8B -139.8(6) . . . . ?
C12B C7B C8B C9B -1.4(8) . . . . ?
C2B C7B C8B C9B 177.0(5) . . . . ?
C7B C8B C9B C10B 0.6(10) . . . . ?
C8B C9B C10B C11B 1.4(14) . . . . ?
C8B C9B C10B Cl1B -179.8(6) . . . . ?
C9B C10B C11B C12B -2.5(14) . . . . ?
Cl1B C10B C11B C12B 178.7(7) . . . . ?
C8B C7B C12B C11B 0.2(10) . . . . ?
C2B C7B C12B C11B -178.0(6) . . . . ?
C10B C11B C12B C7B 1.7(13) . . . . ?
O2B S1B C13B C14B 4.3(3) . . . . ?
O3B S1B C13B C14B -124.9(3) . . . . ?
N1B S1B C13B C14B 123.2(3) . . . . ?
O2B S1B C13B C18B 179.5(3) . . . . ?
O3B S1B C13B C18B 50.3(3) . . . . ?
N1B S1B C13B C18B -61.6(3) . . . . ?
C18B C13B C14B C15B -1.6(5) . . . . ?
S1B C13B C14B C15B 173.5(3) . . . . ?
C13B C14B C15B C16B 0.5(5) . . . . ?
C14B C15B C16B C17B 1.1(5) . . . . ?
C14B C15B C16B C19B -179.3(3) . . . . ?
C15B C16B C17B C18B -1.5(6) . . . . ?
C19B C16B C17B C18B 178.9(3) . . . . ?
C16B C17B C18B C13B 0.4(5) . . . . ?
C14B C13B C18B C17B 1.2(5) . . . . ?
S1B C13B C18B C17B -173.9(3) . . . . ?
O1B C1B C2D C3D -151.0(15) . . . . ?
N1B C1B C2D C3D 41(2) . . . . ?
O1B C1B C2D C7D -6(2) . . . . ?
N1B C1B C2D C7D -173.9(16) . . . . ?
O1B C1B C2D C6D 139.3(16) . . . . ?
N1B C1B C2D C6D -29(2) . . . . ?
C1B C2D C3D C6D -119(2) . . . . ?
C7D C2D C3D C6D 99(2) . . . . ?
C1B C2D C3D C4D -12(3) . . . . ?
C7D C2D C3D C4D -154(2) . . . . ?
C6D C2D C3D C4D 107(2) . . . . ?
C6D C3D C4D C5D 37(3) . . . . ?
C2D C3D C4D C5D -33(3) . . . . ?
C3D C4D C5D N1B 50(3) . . . . ?
C1B N1B C5D C4D -21(4) . . . . ?
S1B N1B C5D C4D 138(2) . . . . ?
C4D C3D C6D C2D -106.3(19) . . . . ?
C1B C2D C6D C3D 103(2) . . . . ?
C7D C2D C6D C3D -111.4(19) . . . . ?
C3D C2D C7D C12D 65(3) . . . . ?
C1B C2D C7D C12D -80(3) . . . . ?
C6D C2D C7D C12D 129(3) . . . . ?
C3D C2D C7D C8D -115(3) . . . . ?
C1B C2D C7D C8D 100(3) . . . . ?
C6D C2D C7D C8D -51(3) . . . . ?
C12D C7D C8D C9D 1(3) . . . . ?
C2D C7D C8D C9D -180(2) . . . . ?
C7D C8D C9D C10D -2(5) . . . . ?
C8D C9D C10D C11D 2(7) . . . . ?
C8D C9D C10D Cl1D 180(3) . . . . ?
C9D C10D C11D C12D -2(8) . . . . ?
Cl1D C10D C11D C12D -180(4) . . . . ?
C8D C7D C12D C11D 0(5) . . . . ?
C2D C7D C12D C11D -180(3) . . . . ?
C10D C11D C12D C7D 1(7) . . . . ?

_refine_diff_density_max         0.262
_refine_diff_density_min         -0.414
_refine_diff_density_rms         0.048

