# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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. 
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data_mo_170523K_0m
_database_code_depnum_ccdc_archive 'CCDC 1558505'
_audit_update_record             
;
2017-06-26 deposited with the CCDC.
2018-07-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23.50 H28 Cl3 N3 O6 S2'
_chemical_formula_weight         618.96

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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                   8.139(3)
_cell_length_b                   13.440(4)
_cell_length_c                   13.650(5)
_cell_angle_alpha                102.732(5)
_cell_angle_beta                 104.959(5)
_cell_angle_gamma                107.249(5)
_cell_volume                     1304.4(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2357
_cell_measurement_theta_min      2.67
_cell_measurement_theta_max      26.12

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      1.576
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.576
_exptl_crystal_F_000             642
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.558
_shelx_estimated_absorpt_T_min   0.936
_shelx_estimated_absorpt_T_max   0.946
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8991
_diffrn_reflns_av_unetI/netI     0.0765
_diffrn_reflns_av_R_equivalents  0.0470
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.631
_diffrn_reflns_theta_max         25.050
_diffrn_reflns_theta_full        25.050
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.982
_reflns_number_total             4528
_reflns_number_gt                3589
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0959P)²+4.9585P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0031(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4528
_refine_ls_number_parameters     353
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0873
_refine_ls_R_factor_gt           0.0695
_refine_ls_wR_factor_ref         0.2048
_refine_ls_wR_factor_gt          0.1896
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_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
C1 C 0.6410(7) 0.7744(4) 0.2409(4) 0.0201(11) Uani 1 1 d . . . . .
H1A H 0.7378 0.8476 0.2839 0.024 Uiso 1 1 calc R U . . .
H1B H 0.6579 0.7221 0.2799 0.024 Uiso 1 1 calc R U . . .
C2 C 0.4564(7) 0.7810(4) 0.2299(4) 0.0167(11) Uani 1 1 d . . . . .
H2A H 0.4490 0.8073 0.3017 0.020 Uiso 1 1 calc R U . . .
H2B H 0.4387 0.8339 0.1918 0.020 Uiso 1 1 calc R U . . .
C3 C 0.3319(7) 0.6354(4) 0.0644(4) 0.0186(11) Uani 1 1 d . . . . .
H3A H 0.3098 0.6857 0.0239 0.022 Uiso 1 1 calc R U . . .
H3B H 0.2395 0.5606 0.0227 0.022 Uiso 1 1 calc R U . . .
C4 C 0.5217(7) 0.6351(4) 0.0789(4) 0.0220(12) Uani 1 1 d . . . . .
H4A H 0.5396 0.5808 0.1150 0.026 Uiso 1 1 calc R U . . .
H4B H 0.5327 0.6116 0.0077 0.026 Uiso 1 1 calc R U . . .
C5 C 0.1293(7) 0.6729(4) 0.1536(4) 0.0175(11) Uani 1 1 d . . . . .
H5A H 0.0386 0.6014 0.1016 0.021 Uiso 1 1 calc R U . . .
H5B H 0.1178 0.7308 0.1214 0.021 Uiso 1 1 calc R U . . .
C6 C 0.0816(7) 0.6935(4) 0.2547(4) 0.0155(10) Uani 1 1 d . . . . .
H6A H 0.1716 0.7652 0.3068 0.019 Uiso 1 1 calc R U . . .
H6B H -0.0410 0.6983 0.2370 0.019 Uiso 1 1 calc R U . . .
C7 C 0.2283(7) 0.6297(4) 0.3976(4) 0.0151(10) Uani 1 1 d . . . . .
C8 C 0.2189(7) 0.5422(4) 0.4476(4) 0.0145(10) Uani 1 1 d . . . . .
C9 C 0.3589(7) 0.5630(4) 0.5403(4) 0.0153(10) Uani 1 1 d . . . . .
H9 H 0.4585 0.6322 0.5711 0.018 Uiso 1 1 calc R U . . .
C10 C 0.3529(7) 0.4809(4) 0.5891(4) 0.0168(10) Uani 1 1 d . . . . .
H10 H 0.4477 0.4959 0.6543 0.020 Uiso 1 1 calc R U . . .
C11 C 0.2144(7) 0.3803(4) 0.5450(4) 0.0151(10) Uani 1 1 d . . . . .
H11 H 0.2154 0.3261 0.5792 0.018 Uiso 1 1 calc R U . . .
C12 C 0.0682(6) 0.3550(4) 0.4485(4) 0.0131(10) Uani 1 1 d . . . . .
C13 C -0.0858(7) 0.2528(4) 0.3967(4) 0.0138(10) Uani 1 1 d . . . . .
C14 C -0.2264(7) 0.2391(4) 0.3062(4) 0.0158(10) Uani 1 1 d . . . . .
H14 H -0.3283 0.1711 0.2737 0.019 Uiso 1 1 calc R U . . .
C15 C -0.2210(7) 0.3229(4) 0.2624(4) 0.0170(10) Uani 1 1 d . . . . .
H15 H -0.3199 0.3124 0.2010 0.020 Uiso 1 1 calc R U . . .
C16 C -0.0729(7) 0.4219(4) 0.3071(4) 0.0133(10) Uani 1 1 d . . . . .
C17 C -0.0726(7) 0.5096(4) 0.2595(4) 0.0138(10) Uani 1 1 d . . . . .
C18 C 0.0723(6) 0.4392(4) 0.4002(4) 0.0116(10) Uani 1 1 d . . . . .
C19 C 0.2267(6) 0.1322(4) 0.4377(4) 0.0139(10) Uani 1 1 d . . . . .
H19A H 0.2555 0.1518 0.5162 0.017 Uiso 1 1 calc R U . . .
H19B H 0.2744 0.2008 0.4209 0.017 Uiso 1 1 calc R U . . .
C20 C 0.3202(7) 0.0541(4) 0.4022(4) 0.0166(10) Uani 1 1 d . . . . .
H20A H 0.2682 -0.0157 0.4161 0.020 Uiso 1 1 calc R U . . .
H20B H 0.4530 0.0878 0.4448 0.020 Uiso 1 1 calc R U . . .
C21 C 0.0416(7) -0.0298(5) 0.2162(4) 0.0255(12) Uani 1 1 d . . . . .
H21A H -0.0072 -0.0502 0.1372 0.031 Uiso 1 1 calc R U . . .
H21B H -0.0011 -0.0973 0.2355 0.031 Uiso 1 1 calc R U . . .
C22 C -0.0334(7) 0.0523(4) 0.2649(4) 0.0162(10) Uani 1 1 d . . . . .
H22A H 0.0103 0.1203 0.2464 0.019 Uiso 1 1 calc R U . . .
H22B H -0.1690 0.0208 0.2342 0.019 Uiso 1 1 calc R U . . .
C23 C 0.8159(8) 0.7436(5) 0.9134(5) 0.0305(13) Uani 1 1 d . . . . .
H23A H 0.7370 0.7667 0.8621 0.037 Uiso 1 1 calc R U . . .
H23B H 0.7801 0.7513 0.9779 0.037 Uiso 1 1 calc R U . . .
Cl1 Cl 1.0479(2) 0.83091(12) 0.94993(11) 0.0330(4) Uani 1 1 d . . . . .
Cl2 Cl 0.7790(2) 0.60454(12) 0.85466(12) 0.0330(4) Uani 1 1 d . . . . .
C24 C 0.4925(17) 0.9865(10) 0.9478(9) 0.030(3) Uani 0.5 1 d . . P A -1
H24A H 0.5903 1.0270 0.9246 0.036 Uiso 0.5 1 calc R U P A -1
H24B H 0.3839 0.9400 0.8830 0.036 Uiso 0.5 1 calc R U P A -1
Cl3 Cl 0.5690(5) 0.9012(3) 1.0147(3) 0.0294(9) Uani 0.5 1 d . . P A -1
Cl4 Cl 0.4351(5) 1.0808(3) 1.0289(3) 0.0338(9) Uani 0.5 1 d . . P A -1
N1 N 0.3124(6) 0.6716(3) 0.1697(3) 0.0150(9) Uani 1 1 d . . . . .
N2 N 0.0808(6) 0.6073(3) 0.3052(3) 0.0144(9) Uani 1 1 d . . . . .
N3 N 0.0257(5) 0.0798(3) 0.3827(3) 0.0119(8) Uani 1 1 d . . . . .
O1 O 0.6610(5) 0.7397(3) 0.1400(3) 0.0200(8) Uani 1 1 d . . . . .
O2 O 0.3560(5) 0.7184(3) 0.4344(3) 0.0201(8) Uani 1 1 d . . . . .
O3 O -0.2000(5) 0.4987(3) 0.1821(3) 0.0188(8) Uani 1 1 d . . . . .
O4 O -0.0204(5) 0.1634(3) 0.5487(3) 0.0150(7) Uani 1 1 d . . . . .
O5 O -0.2864(4) 0.0574(3) 0.3829(3) 0.0173(8) Uani 1 1 d . . . . .
O6 O 0.3430(5) 0.1348(4) 0.2440(3) 0.0389(12) Uani 1 1 d . . . . .
S1 S -0.10070(16) 0.13298(9) 0.43554(9) 0.0124(3) Uani 1 1 d . . . . .
S2 S 0.28897(18) 0.02554(13) 0.26215(11) 0.0245(4) 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 O1 1.422(6) . ?
C1 C2 1.503(7) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 N1 1.470(6) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 N1 1.477(6) . ?
C3 C4 1.508(7) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 O1 1.417(6) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 N1 1.455(6) . ?
C5 C6 1.519(7) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 N2 1.471(6) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 O2 1.218(6) . ?
C7 N2 1.400(6) . ?
C7 C8 1.478(7) . ?
C8 C9 1.374(7) . ?
C8 C18 1.409(7) . ?
C9 C10 1.404(7) . ?
C9 H9 0.9500 . ?
C10 C11 1.359(7) . ?
C10 H10 0.9500 . ?
C11 C12 1.421(7) . ?
C11 H11 0.9500 . ?
C12 C13 1.432(7) . ?
C12 C18 1.426(7) . ?
C13 C14 1.384(7) . ?
C13 S1 1.784(5) . ?
C14 C15 1.382(7) . ?
C14 H14 0.9500 . ?
C15 C16 1.381(7) . ?
C15 H15 0.9500 . ?
C16 C18 1.414(7) . ?
C16 C17 1.465(7) . ?
C17 O3 1.220(6) . ?
C17 N2 1.392(6) . ?
C19 N3 1.478(6) . ?
C19 C20 1.536(7) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 S2 1.798(5) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.521(7) . ?
C21 S2 1.804(6) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 N3 1.479(6) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 Cl1 1.770(6) . ?
C23 Cl2 1.763(6) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 Cl4 1.746(12) . ?
C24 Cl3 1.767(12) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
N3 S1 1.638(4) . ?
O4 S1 1.422(4) . ?
O5 S1 1.428(4) . ?
O6 S2 1.497(5) . ?

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
O1 C1 C2 112.2(4) . . ?
O1 C1 H1A 109.2 . . ?
C2 C1 H1A 109.2 . . ?
O1 C1 H1B 109.2 . . ?
C2 C1 H1B 109.2 . . ?
H1A C1 H1B 107.9 . . ?
N1 C2 C1 109.4(4) . . ?
N1 C2 H2A 109.8 . . ?
C1 C2 H2A 109.8 . . ?
N1 C2 H2B 109.8 . . ?
C1 C2 H2B 109.8 . . ?
H2A C2 H2B 108.2 . . ?
N1 C3 C4 110.2(4) . . ?
N1 C3 H3A 109.6 . . ?
C4 C3 H3A 109.6 . . ?
N1 C3 H3B 109.6 . . ?
C4 C3 H3B 109.6 . . ?
H3A C3 H3B 108.1 . . ?
O1 C4 C3 112.5(4) . . ?
O1 C4 H4A 109.1 . . ?
C3 C4 H4A 109.1 . . ?
O1 C4 H4B 109.1 . . ?
C3 C4 H4B 109.1 . . ?
H4A C4 H4B 107.8 . . ?
N1 C5 C6 114.6(4) . . ?
N1 C5 H5A 108.6 . . ?
C6 C5 H5A 108.6 . . ?
N1 C5 H5B 108.6 . . ?
C6 C5 H5B 108.6 . . ?
H5A C5 H5B 107.6 . . ?
N2 C6 C5 113.3(4) . . ?
N2 C6 H6A 108.9 . . ?
C5 C6 H6A 108.9 . . ?
N2 C6 H6B 108.9 . . ?
C5 C6 H6B 108.9 . . ?
H6A C6 H6B 107.7 . . ?
O2 C7 N2 120.5(4) . . ?
O2 C7 C8 122.6(4) . . ?
N2 C7 C8 116.8(4) . . ?
C9 C8 C18 120.8(4) . . ?
C9 C8 C7 118.3(4) . . ?
C18 C8 C7 120.9(4) . . ?
C8 C9 C10 119.2(5) . . ?
C8 C9 H9 120.4 . . ?
C10 C9 H9 120.4 . . ?
C11 C10 C9 121.4(5) . . ?
C11 C10 H10 119.3 . . ?
C9 C10 H10 119.3 . . ?
C10 C11 C12 121.1(4) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 H11 119.4 . . ?
C11 C12 C13 125.6(4) . . ?
C11 C12 C18 117.4(4) . . ?
C13 C12 C18 117.0(4) . . ?
C14 C13 C12 120.8(4) . . ?
C14 C13 S1 115.8(4) . . ?
C12 C13 S1 123.2(4) . . ?
C15 C14 C13 121.0(5) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C14 C15 C16 120.5(5) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C15 C16 C18 119.9(4) . . ?
C15 C16 C17 119.1(4) . . ?
C18 C16 C17 120.9(4) . . ?
O3 C17 N2 120.2(4) . . ?
O3 C17 C16 122.3(4) . . ?
N2 C17 C16 117.5(4) . . ?
C8 C18 C16 119.3(4) . . ?
C8 C18 C12 120.0(4) . . ?
C16 C18 C12 120.7(4) . . ?
N3 C19 C20 110.6(4) . . ?
N3 C19 H19A 109.5 . . ?
C20 C19 H19A 109.5 . . ?
N3 C19 H19B 109.5 . . ?
C20 C19 H19B 109.5 . . ?
H19A C19 H19B 108.1 . . ?
C19 C20 S2 111.3(3) . . ?
C19 C20 H20A 109.4 . . ?
S2 C20 H20A 109.4 . . ?
C19 C20 H20B 109.4 . . ?
S2 C20 H20B 109.4 . . ?
H20A C20 H20B 108.0 . . ?
C22 C21 S2 111.9(4) . . ?
C22 C21 H21A 109.2 . . ?
S2 C21 H21A 109.2 . . ?
C22 C21 H21B 109.2 . . ?
S2 C21 H21B 109.2 . . ?
H21A C21 H21B 107.9 . . ?
N3 C22 C21 111.3(4) . . ?
N3 C22 H22A 109.4 . . ?
C21 C22 H22A 109.4 . . ?
N3 C22 H22B 109.4 . . ?
C21 C22 H22B 109.4 . . ?
H22A C22 H22B 108.0 . . ?
Cl1 C23 Cl2 112.0(3) . . ?
Cl1 C23 H23A 109.2 . . ?
Cl2 C23 H23A 109.2 . . ?
Cl1 C23 H23B 109.2 . . ?
Cl2 C23 H23B 109.2 . . ?
H23A C23 H23B 107.9 . . ?
Cl4 C24 Cl3 112.3(6) . . ?
Cl4 C24 H24A 109.1 . . ?
Cl3 C24 H24A 109.1 . . ?
Cl4 C24 H24B 109.1 . . ?
Cl3 C24 H24B 109.1 . . ?
H24A C24 H24B 107.9 . . ?
C5 N1 C2 112.1(4) . . ?
C5 N1 C3 109.2(4) . . ?
C2 N1 C3 107.6(4) . . ?
C17 N2 C7 124.3(4) . . ?
C17 N2 C6 117.0(4) . . ?
C7 N2 C6 118.7(4) . . ?
C19 N3 C22 114.1(4) . . ?
C19 N3 S1 117.1(3) . . ?
C22 N3 S1 113.5(3) . . ?
C4 O1 C1 108.8(4) . . ?
O5 S1 O4 119.4(2) . . ?
O5 S1 N3 107.1(2) . . ?
O4 S1 N3 107.5(2) . . ?
O5 S1 C13 106.6(2) . . ?
O4 S1 C13 110.0(2) . . ?
N3 S1 C13 105.3(2) . . ?
O6 S2 C20 106.3(3) . . ?
O6 S2 C21 106.0(3) . . ?
C20 S2 C21 95.5(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
O1 C1 C2 N1 61.0(5) . . . . ?
N1 C3 C4 O1 -58.1(5) . . . . ?
N1 C5 C6 N2 -62.7(6) . . . . ?
O2 C7 C8 C9 1.1(7) . . . . ?
N2 C7 C8 C9 -178.0(4) . . . . ?
O2 C7 C8 C18 -177.6(5) . . . . ?
N2 C7 C8 C18 3.4(7) . . . . ?
C18 C8 C9 C10 -1.2(7) . . . . ?
C7 C8 C9 C10 -179.9(4) . . . . ?
C8 C9 C10 C11 1.8(8) . . . . ?
C9 C10 C11 C12 -1.1(8) . . . . ?
C10 C11 C12 C13 -178.7(5) . . . . ?
C10 C11 C12 C18 -0.2(7) . . . . ?
C11 C12 C13 C14 176.1(5) . . . . ?
C18 C12 C13 C14 -2.4(7) . . . . ?
C11 C12 C13 S1 -9.6(7) . . . . ?
C18 C12 C13 S1 172.0(3) . . . . ?
C12 C13 C14 C15 1.0(7) . . . . ?
S1 C13 C14 C15 -173.7(4) . . . . ?
C13 C14 C15 C16 1.1(8) . . . . ?
C14 C15 C16 C18 -1.7(7) . . . . ?
C14 C15 C16 C17 -179.2(5) . . . . ?
C15 C16 C17 O3 0.9(7) . . . . ?
C18 C16 C17 O3 -176.6(5) . . . . ?
C15 C16 C17 N2 -178.5(4) . . . . ?
C18 C16 C17 N2 4.0(7) . . . . ?
C9 C8 C18 C16 177.6(4) . . . . ?
C7 C8 C18 C16 -3.8(7) . . . . ?
C9 C8 C18 C12 -0.1(7) . . . . ?
C7 C8 C18 C12 178.5(4) . . . . ?
C15 C16 C18 C8 -177.4(4) . . . . ?
C17 C16 C18 C8 0.0(7) . . . . ?
C15 C16 C18 C12 0.3(7) . . . . ?
C17 C16 C18 C12 177.7(4) . . . . ?
C11 C12 C18 C8 0.8(7) . . . . ?
C13 C12 C18 C8 179.4(4) . . . . ?
C11 C12 C18 C16 -176.9(4) . . . . ?
C13 C12 C18 C16 1.7(7) . . . . ?
N3 C19 C20 S2 64.3(4) . . . . ?
S2 C21 C22 N3 -62.7(5) . . . . ?
C6 C5 N1 C2 -68.9(5) . . . . ?
C6 C5 N1 C3 172.0(4) . . . . ?
C1 C2 N1 C5 -178.4(4) . . . . ?
C1 C2 N1 C3 -58.4(5) . . . . ?
C4 C3 N1 C5 179.1(4) . . . . ?
C4 C3 N1 C2 57.2(5) . . . . ?
O3 C17 N2 C7 176.1(5) . . . . ?
C16 C17 N2 C7 -4.5(7) . . . . ?
O3 C17 N2 C6 -1.1(7) . . . . ?
C16 C17 N2 C6 178.3(4) . . . . ?
O2 C7 N2 C17 -178.2(5) . . . . ?
C8 C7 N2 C17 0.9(7) . . . . ?
O2 C7 N2 C6 -1.0(7) . . . . ?
C8 C7 N2 C6 178.0(4) . . . . ?
C5 C6 N2 C17 -78.4(5) . . . . ?
C5 C6 N2 C7 104.2(5) . . . . ?
C20 C19 N3 C22 -62.2(5) . . . . ?
C20 C19 N3 S1 161.7(3) . . . . ?
C21 C22 N3 C19 61.6(5) . . . . ?
C21 C22 N3 S1 -160.7(4) . . . . ?
C3 C4 O1 C1 57.1(5) . . . . ?
C2 C1 O1 C4 -58.7(5) . . . . ?
C19 N3 S1 O5 -168.6(3) . . . . ?
C22 N3 S1 O5 55.1(4) . . . . ?
C19 N3 S1 O4 -39.1(4) . . . . ?
C22 N3 S1 O4 -175.4(3) . . . . ?
C19 N3 S1 C13 78.2(4) . . . . ?
C22 N3 S1 C13 -58.1(4) . . . . ?
C14 C13 S1 O5 -18.0(4) . . . . ?
C12 C13 S1 O5 167.4(4) . . . . ?
C14 C13 S1 O4 -148.8(4) . . . . ?
C12 C13 S1 O4 36.5(5) . . . . ?
C14 C13 S1 N3 95.6(4) . . . . ?
C12 C13 S1 N3 -79.1(4) . . . . ?
C19 C20 S2 O6 50.3(4) . . . . ?
C19 C20 S2 C21 -58.1(4) . . . . ?
C22 C21 S2 O6 -51.2(5) . . . . ?
C22 C21 S2 C20 57.5(4) . . . . ?

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
C24 H24A S2 0.99 2.98 3.742(12) 134.8 2_666
C24 H24A Cl1 0.99 2.81 3.509(13) 128.5 2_777
C23 H23A O6 0.99 2.27 3.214(7) 159.3 2_666
C23 H23B O1 0.99 2.65 3.633(7) 171.5 1_556
C22 H22B Cl3 0.99 2.94 3.688(6) 133.0 1_444
C22 H22A Cl1 0.99 2.85 3.610(5) 133.9 2_666
C21 H21A Cl1 0.99 2.92 3.725(6) 139.5 1_444
C20 H20B O5 0.99 2.58 3.268(6) 126.4 1_655
C20 H20B O2 0.99 2.51 3.233(6) 129.6 2_666
C20 H20A O4 0.99 2.60 3.525(6) 154.7 2_556
C14 H14 O6 0.95 2.48 3.161(6) 128.9 1_455
C5 H5B Cl1 0.99 2.96 3.893(5) 157.5 1_454
C5 H5A O3 0.99 2.66 3.168(6) 112.3 .
C3 H3B O3 0.99 2.64 3.168(6) 113.7 2_565
C2 H2A O2 0.99 2.53 3.313(6) 135.7 .

_refine_diff_density_max         0.773
_refine_diff_density_min         -0.601
_refine_diff_density_rms         0.129

####################################################################### 
# 
# 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_mo_170503D_0m
_database_code_depnum_ccdc_archive 'CCDC 1558506'
_audit_update_record             
;
2017-06-26 deposited with the CCDC.
2018-07-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H27 Cl2 N3 O5 S2'
_chemical_formula_weight         560.49

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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                   9.0264(16)
_cell_length_b                   9.0426(16)
_cell_length_c                   17.336(3)
_cell_angle_alpha                76.843(3)
_cell_angle_beta                 80.437(3)
_cell_angle_gamma                65.448(3)
_cell_volume                     1249.2(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3243
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      27.88

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      1.490
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.490
_exptl_crystal_F_000             584
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.468
_shelx_estimated_absorpt_T_min   0.912
_shelx_estimated_absorpt_T_max   0.933
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8783
_diffrn_reflns_av_unetI/netI     0.0378
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.421
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             4362
_reflns_number_gt                3353
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.1339P)²+1.7514P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4362
_refine_ls_number_parameters     316
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0939
_refine_ls_R_factor_gt           0.0762
_refine_ls_wR_factor_ref         0.2441
_refine_ls_wR_factor_gt          0.2196
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_refine_ls_shift/su_max          0.003
_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
C1 C 0.7700(6) -0.0489(6) 1.3142(3) 0.0593(12) Uani 1 1 d . . . . .
H1A H 0.8755 -0.1402 1.3209 0.071 Uiso 1 1 calc R U . . .
H1B H 0.7025 -0.0842 1.2909 0.071 Uiso 1 1 calc R U . . .
C2 C 0.7936(5) 0.0959(6) 1.2581(3) 0.0508(10) Uani 1 1 d . . . . .
H2A H 0.8675 0.1260 1.2797 0.061 Uiso 1 1 calc R U . . .
H2B H 0.8443 0.0623 1.2076 0.061 Uiso 1 1 calc R U . . .
C3 C 0.5519(7) 0.3083(6) 1.3157(3) 0.0600(12) Uani 1 1 d . . . . .
H3A H 0.4546 0.4057 1.3010 0.072 Uiso 1 1 calc R U . . .
H3B H 0.6208 0.3415 1.3394 0.072 Uiso 1 1 calc R U . . .
C4 C 0.5031(7) 0.1823(7) 1.3765(3) 0.0721(15) Uani 1 1 d . . . . .
H4A H 0.4320 0.1515 1.3531 0.087 Uiso 1 1 calc R U . . .
H4B H 0.4419 0.2327 1.4219 0.087 Uiso 1 1 calc R U . . .
C5 C 0.6597(5) 0.2954(5) 1.0862(2) 0.0388(9) Uani 1 1 d . . . . .
C6 C 0.7406(5) 0.1715(5) 1.0441(2) 0.0453(9) Uani 1 1 d . . . . .
H6 H 0.7294 0.0712 1.0611 0.054 Uiso 1 1 calc R U . . .
C7 C 0.8414(5) 0.1928(5) 0.9748(2) 0.0437(9) Uani 1 1 d . . . . .
H7 H 0.8947 0.1079 0.9456 0.052 Uiso 1 1 calc R U . . .
C8 C 0.8601(5) 0.3388(5) 0.9507(2) 0.0373(8) Uani 1 1 d . . . . .
C9 C 0.7765(4) 0.4704(4) 0.9927(2) 0.0351(8) Uani 1 1 d . . . . .
C10 C 0.6729(4) 0.4514(5) 1.0624(2) 0.0356(8) Uani 1 1 d . . . . .
C11 C 0.5926(5) 0.5875(5) 1.1019(2) 0.0460(10) Uani 1 1 d . . . . .
H11 H 0.5252 0.5781 1.1479 0.055 Uiso 1 1 calc R U . . .
C12 C 0.6120(6) 0.7342(6) 1.0737(3) 0.0550(11) Uani 1 1 d . . . . .
H12 H 0.5574 0.8224 1.1007 0.066 Uiso 1 1 calc R U . . .
C13 C 0.7122(5) 0.7513(5) 1.0054(3) 0.0485(10) Uani 1 1 d . . . . .
H13 H 0.7236 0.8512 0.9867 0.058 Uiso 1 1 calc R U . . .
C14 C 0.7942(5) 0.6227(5) 0.9652(2) 0.0391(9) Uani 1 1 d . . . . .
C15 C 0.8999(5) 0.6446(5) 0.8919(2) 0.0443(9) Uani 1 1 d . . . . .
C16 C 0.9697(5) 0.3582(5) 0.8782(2) 0.0436(9) Uani 1 1 d . . . . .
C17 C 1.0827(5) 0.5326(6) 0.7799(2) 0.0503(10) Uani 1 1 d . . . . .
H17A H 1.1696 0.4274 0.7723 0.060 Uiso 1 1 calc R U . . .
H17B H 1.1324 0.6069 0.7841 0.060 Uiso 1 1 calc R U . . .
C18 C 0.9803(6) 0.6036(7) 0.7089(3) 0.0583(12) Uani 1 1 d . . . . .
H18A H 0.9294 0.5300 0.7052 0.070 Uiso 1 1 calc R U . . .
H18B H 0.8943 0.7095 0.7162 0.070 Uiso 1 1 calc R U . . .
C19 C 1.1718(10) 0.4685(8) 0.6082(4) 0.095(2) Uani 1 1 d . . . . .
H19A H 1.0970 0.4236 0.5988 0.113 Uiso 1 1 calc R U . . .
H19B H 1.2419 0.3902 0.6485 0.113 Uiso 1 1 calc R U . . .
C20 C 1.2732(13) 0.4947(12) 0.5329(5) 0.130(3) Uani 1 1 d . . . . .
H20A H 1.3493 0.5371 0.5432 0.156 Uiso 1 1 calc R U . . .
H20B H 1.3365 0.3893 0.5160 0.156 Uiso 1 1 calc R U . . .
C21 C 1.0922(10) 0.7580(12) 0.4983(4) 0.110(3) Uani 1 1 d . . . . .
H21A H 1.0270 0.8372 0.4564 0.132 Uiso 1 1 calc R U . . .
H21B H 1.1690 0.7994 0.5087 0.132 Uiso 1 1 calc R U . . .
C22 C 0.9815(8) 0.7419(10) 0.5730(3) 0.100(2) Uani 1 1 d . . . . .
H22A H 0.9230 0.8485 0.5893 0.120 Uiso 1 1 calc R U . . .
H22B H 0.9021 0.7039 0.5626 0.120 Uiso 1 1 calc R U . . .
C23 C 0.2889(17) 0.9048(12) 0.2661(7) 0.159(4) Uani 1 1 d . . . . .
H23A H 0.1945 1.0043 0.2749 0.191 Uiso 1 1 calc R U . . .
H23B H 0.3563 0.9371 0.2215 0.191 Uiso 1 1 calc R U . . .
Cl1 Cl 0.3974(5) 0.8380(5) 0.34749(19) 0.1950(17) Uani 1 1 d . . . . .
Cl2 Cl 0.2239(3) 0.7853(3) 0.23883(15) 0.1207(8) Uani 1 1 d . . . . .
N1 N 0.6398(4) 0.2419(4) 1.24425(19) 0.0436(8) Uani 1 1 d . . . . .
N2 N 0.9817(4) 0.5093(4) 0.85373(18) 0.0433(8) Uani 1 1 d . . . . .
N3 N 1.0800(4) 0.6249(5) 0.6355(2) 0.0498(9) Uani 1 1 d . . . . .
O1 O 0.5346(4) 0.0957(4) 1.17150(17) 0.0587(9) Uani 1 1 d . . . . .
O2 O 0.3848(3) 0.3893(4) 1.17748(18) 0.0578(8) Uani 1 1 d . . . . .
O3 O 1.0471(4) 0.2451(4) 0.84254(19) 0.0640(9) Uani 1 1 d . . . . .
O4 O 0.9150(5) 0.7743(4) 0.8661(2) 0.0649(9) Uani 1 1 d . . . . .
O5 O 1.1800(9) 0.6033(10) 0.4724(3) 0.125(2) Uani 1 1 d . . . . .
S1 S 0.6763(2) -0.0005(2) 1.40995(7) 0.0765(5) Uani 1 1 d . . . . .
S2 S 0.53730(12) 0.25219(13) 1.17299(5) 0.0425(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.513(6) . ?
C1 S1 1.794(5) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 N1 1.473(5) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 N1 1.463(6) . ?
C3 C4 1.523(8) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 S1 1.797(6) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.356(6) . ?
C5 C10 1.425(5) . ?
C5 S2 1.782(4) . ?
C6 C7 1.409(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.362(6) . ?
C7 H7 0.9300 . ?
C8 C9 1.408(5) . ?
C8 C16 1.491(5) . ?
C9 C14 1.418(5) . ?
C9 C10 1.423(5) . ?
C10 C11 1.410(6) . ?
C11 C12 1.377(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.386(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.367(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.483(5) . ?
C15 O4 1.212(5) . ?
C15 N2 1.391(5) . ?
C16 O3 1.211(5) . ?
C16 N2 1.379(5) . ?
C17 N2 1.470(5) . ?
C17 C18 1.519(6) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 N3 1.455(5) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 N3 1.452(7) . ?
C19 C20 1.496(9) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 O5 1.383(12) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 O5 1.426(11) . ?
C21 C22 1.517(8) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 N3 1.450(7) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 Cl2 1.609(10) . ?
C23 Cl1 1.701(12) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
N1 S2 1.627(3) . ?
O1 S2 1.432(3) . ?
O2 S2 1.424(3) . ?

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
C2 C1 S1 112.8(4) . . ?
C2 C1 H1A 109.0 . . ?
S1 C1 H1A 109.0 . . ?
C2 C1 H1B 109.0 . . ?
S1 C1 H1B 109.0 . . ?
H1A C1 H1B 107.8 . . ?
N1 C2 C1 113.3(4) . . ?
N1 C2 H2A 108.9 . . ?
C1 C2 H2A 108.9 . . ?
N1 C2 H2B 108.9 . . ?
C1 C2 H2B 108.9 . . ?
H2A C2 H2B 107.7 . . ?
N1 C3 C4 111.9(4) . . ?
N1 C3 H3A 109.2 . . ?
C4 C3 H3A 109.2 . . ?
N1 C3 H3B 109.2 . . ?
C4 C3 H3B 109.2 . . ?
H3A C3 H3B 107.9 . . ?
C3 C4 S1 112.6(4) . . ?
C3 C4 H4A 109.1 . . ?
S1 C4 H4A 109.1 . . ?
C3 C4 H4B 109.1 . . ?
S1 C4 H4B 109.1 . . ?
H4A C4 H4B 107.8 . . ?
C6 C5 C10 121.6(3) . . ?
C6 C5 S2 116.4(3) . . ?
C10 C5 S2 122.0(3) . . ?
C5 C6 C7 120.8(4) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 H6 119.6 . . ?
C8 C7 C6 119.5(4) . . ?
C8 C7 H7 120.3 . . ?
C6 C7 H7 120.3 . . ?
C7 C8 C9 121.0(3) . . ?
C7 C8 C16 118.9(3) . . ?
C9 C8 C16 120.1(3) . . ?
C8 C9 C14 120.0(3) . . ?
C8 C9 C10 120.1(3) . . ?
C14 C9 C10 119.9(3) . . ?
C11 C10 C9 117.5(3) . . ?
C11 C10 C5 125.6(3) . . ?
C9 C10 C5 116.9(3) . . ?
C12 C11 C10 121.4(4) . . ?
C12 C11 H11 119.3 . . ?
C10 C11 H11 119.3 . . ?
C11 C12 C13 120.5(4) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C14 C13 C12 120.6(4) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C13 C14 C9 120.1(4) . . ?
C13 C14 C15 119.5(4) . . ?
C9 C14 C15 120.3(4) . . ?
O4 C15 N2 121.0(4) . . ?
O4 C15 C14 121.8(4) . . ?
N2 C15 C14 117.2(3) . . ?
O3 C16 N2 121.1(4) . . ?
O3 C16 C8 121.3(4) . . ?
N2 C16 C8 117.5(3) . . ?
N2 C17 C18 110.8(3) . . ?
N2 C17 H17A 109.5 . . ?
C18 C17 H17A 109.5 . . ?
N2 C17 H17B 109.5 . . ?
C18 C17 H17B 109.5 . . ?
H17A C17 H17B 108.1 . . ?
N3 C18 C17 111.1(3) . . ?
N3 C18 H18A 109.4 . . ?
C17 C18 H18A 109.4 . . ?
N3 C18 H18B 109.4 . . ?
C17 C18 H18B 109.4 . . ?
H18A C18 H18B 108.0 . . ?
N3 C19 C20 109.6(5) . . ?
N3 C19 H19A 109.8 . . ?
C20 C19 H19A 109.8 . . ?
N3 C19 H19B 109.8 . . ?
C20 C19 H19B 109.8 . . ?
H19A C19 H19B 108.2 . . ?
O5 C20 C19 112.6(8) . . ?
O5 C20 H20A 109.1 . . ?
C19 C20 H20A 109.1 . . ?
O5 C20 H20B 109.1 . . ?
C19 C20 H20B 109.1 . . ?
H20A C20 H20B 107.8 . . ?
O5 C21 C22 111.3(7) . . ?
O5 C21 H21A 109.4 . . ?
C22 C21 H21A 109.4 . . ?
O5 C21 H21B 109.4 . . ?
C22 C21 H21B 109.4 . . ?
H21A C21 H21B 108.0 . . ?
N3 C22 C21 109.1(5) . . ?
N3 C22 H22A 109.9 . . ?
C21 C22 H22A 109.9 . . ?
N3 C22 H22B 109.9 . . ?
C21 C22 H22B 109.9 . . ?
H22A C22 H22B 108.3 . . ?
Cl2 C23 Cl1 120.2(6) . . ?
Cl2 C23 H23A 107.3 . . ?
Cl1 C23 H23A 107.3 . . ?
Cl2 C23 H23B 107.3 . . ?
Cl1 C23 H23B 107.3 . . ?
H23A C23 H23B 106.9 . . ?
C3 N1 C2 114.7(3) . . ?
C3 N1 S2 119.5(3) . . ?
C2 N1 S2 117.0(3) . . ?
C16 N2 C15 124.9(3) . . ?
C16 N2 C17 118.0(3) . . ?
C15 N2 C17 117.1(3) . . ?
C22 N3 C19 108.7(5) . . ?
C22 N3 C18 111.7(4) . . ?
C19 N3 C18 111.0(4) . . ?
C20 O5 C21 107.7(5) . . ?
C1 S1 C4 97.8(2) . . ?
O2 S2 O1 117.9(2) . . ?
O2 S2 N1 107.22(19) . . ?
O1 S2 N1 112.00(19) . . ?
O2 S2 C5 109.96(19) . . ?
O1 S2 C5 106.19(19) . . ?
N1 S2 C5 102.51(17) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 C1 C2 N1 -58.5(5) . . . . ?
N1 C3 C4 S1 60.8(5) . . . . ?
C10 C5 C6 C7 0.0(6) . . . . ?
S2 C5 C6 C7 -179.6(3) . . . . ?
C5 C6 C7 C8 1.3(6) . . . . ?
C6 C7 C8 C9 -1.9(6) . . . . ?
C6 C7 C8 C16 178.8(4) . . . . ?
C7 C8 C9 C14 -178.1(4) . . . . ?
C16 C8 C9 C14 1.1(5) . . . . ?
C7 C8 C9 C10 1.3(6) . . . . ?
C16 C8 C9 C10 -179.4(3) . . . . ?
C8 C9 C10 C11 179.9(3) . . . . ?
C14 C9 C10 C11 -0.6(5) . . . . ?
C8 C9 C10 C5 0.0(5) . . . . ?
C14 C9 C10 C5 179.4(3) . . . . ?
C6 C5 C10 C11 179.4(4) . . . . ?
S2 C5 C10 C11 -0.9(5) . . . . ?
C6 C5 C10 C9 -0.7(5) . . . . ?
S2 C5 C10 C9 179.0(3) . . . . ?
C9 C10 C11 C12 0.7(6) . . . . ?
C5 C10 C11 C12 -179.3(4) . . . . ?
C10 C11 C12 C13 -0.2(7) . . . . ?
C11 C12 C13 C14 -0.5(7) . . . . ?
C12 C13 C14 C9 0.6(6) . . . . ?
C12 C13 C14 C15 179.6(4) . . . . ?
C8 C9 C14 C13 179.4(4) . . . . ?
C10 C9 C14 C13 0.0(5) . . . . ?
C8 C9 C14 C15 0.4(5) . . . . ?
C10 C9 C14 C15 -179.1(3) . . . . ?
C13 C14 C15 O4 -0.6(6) . . . . ?
C9 C14 C15 O4 178.5(4) . . . . ?
C13 C14 C15 N2 179.5(4) . . . . ?
C9 C14 C15 N2 -1.4(5) . . . . ?
C7 C8 C16 O3 -3.1(6) . . . . ?
C9 C8 C16 O3 177.6(4) . . . . ?
C7 C8 C16 N2 177.7(4) . . . . ?
C9 C8 C16 N2 -1.6(5) . . . . ?
N2 C17 C18 N3 -179.2(4) . . . . ?
N3 C19 C20 O5 -60.5(9) . . . . ?
O5 C21 C22 N3 59.7(8) . . . . ?
C4 C3 N1 C2 -60.7(5) . . . . ?
C4 C3 N1 S2 85.8(5) . . . . ?
C1 C2 N1 C3 60.0(5) . . . . ?
C1 C2 N1 S2 -87.4(4) . . . . ?
O3 C16 N2 C15 -178.7(4) . . . . ?
C8 C16 N2 C15 0.4(6) . . . . ?
O3 C16 N2 C17 4.0(6) . . . . ?
C8 C16 N2 C17 -176.8(3) . . . . ?
O4 C15 N2 C16 -178.9(4) . . . . ?
C14 C15 N2 C16 1.0(6) . . . . ?
O4 C15 N2 C17 -1.6(6) . . . . ?
C14 C15 N2 C17 178.3(3) . . . . ?
C18 C17 N2 C16 91.7(5) . . . . ?
C18 C17 N2 C15 -85.8(5) . . . . ?
C21 C22 N3 C19 -57.0(8) . . . . ?
C21 C22 N3 C18 -179.8(6) . . . . ?
C20 C19 N3 C22 57.0(8) . . . . ?
C20 C19 N3 C18 -179.8(6) . . . . ?
C17 C18 N3 C22 -159.9(5) . . . . ?
C17 C18 N3 C19 78.6(6) . . . . ?
C19 C20 O5 C21 60.4(8) . . . . ?
C22 C21 O5 C20 -59.9(8) . . . . ?
C2 C1 S1 C4 52.0(4) . . . . ?
C3 C4 S1 C1 -53.4(4) . . . . ?
C3 N1 S2 O2 26.4(4) . . . . ?
C2 N1 S2 O2 172.2(3) . . . . ?
C3 N1 S2 O1 -104.4(4) . . . . ?
C2 N1 S2 O1 41.4(3) . . . . ?
C3 N1 S2 C5 142.2(3) . . . . ?
C2 N1 S2 C5 -72.0(3) . . . . ?
C6 C5 S2 O2 -137.1(3) . . . . ?
C10 C5 S2 O2 43.2(4) . . . . ?
C6 C5 S2 O1 -8.5(4) . . . . ?
C10 C5 S2 O1 171.8(3) . . . . ?
C6 C5 S2 N1 109.1(3) . . . . ?
C10 C5 S2 N1 -70.6(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
C23 H23B O1 0.97 2.51 3.357(12) 146.1 1_564
C1 H1B O1 0.97 2.59 3.212(6) 122.4 .
C23 H23B O1 0.97 2.51 3.357(12) 146.1 1_564
C1 H1B O1 0.97 2.59 3.212(6) 122.4 .
C23 H23B O1 0.97 2.51 3.357(12) 146.1 1_564
C1 H1B O1 0.97 2.59 3.212(6) 122.4 .
C23 H23B O1 0.97 2.51 3.357(12) 146.1 1_564
C1 H1B O1 0.97 2.59 3.212(6) 122.4 .
C23 H23B O1 0.97 2.51 3.357(12) 146.1 1_564
C1 H1B O1 0.97 2.59 3.212(6) 122.4 .
C23 H23B O1 0.97 2.51 3.357(12) 146.1 1_564
C1 H1B O1 0.97 2.59 3.212(6) 122.4 .
C23 H23B O1 0.97 2.51 3.357(12) 146.1 1_564
C1 H1B O1 0.97 2.59 3.212(6) 122.4 .
C23 H23B O1 0.97 2.51 3.357(12) 146.1 1_564
C1 H1B O1 0.97 2.59 3.212(6) 122.4 .
C23 H23B O1 0.97 2.51 3.357(12) 146.1 1_564
C1 H1B O1 0.97 2.59 3.212(6) 122.4 .
C1 H1B O1 0.97 2.59 3.212(6) 122.4 .
C23 H23B O1 0.97 2.51 3.357(12) 146.1 1_564
C1 H1B O1 0.97 2.59 3.212(6) 122.4 .
C23 H23B O1 0.97 2.51 3.357(12) 146.1 1_564

_refine_diff_density_max         1.335
_refine_diff_density_min         -1.178
_refine_diff_density_rms         0.083

