# Electronic Supplementary Material (ESI) for Green Chemistry.
# 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_X
_database_code_depnum_ccdc_archive 'CCDC 2056830'
loop_
_audit_author_name
_audit_author_address
'Chengkou Liu'
;Nanjing university of technology
China
;
_audit_update_record             
;
2021-01-18 deposited with the CCDC.	2021-03-23 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            'C25 H22 Cl N O4 S'
_chemical_formula_weight         467.95

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                   12.3598(5)
_cell_length_b                   12.8606(5)
_cell_length_c                   15.4574(6)
_cell_angle_alpha                81.9760(10)
_cell_angle_beta                 75.4550(10)
_cell_angle_gamma                70.6690(10)
_cell_volume                     2239.90(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8312
_cell_measurement_theta_min      5.436
_cell_measurement_theta_max      54.85

_exptl_crystal_description       white
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_F_000             976
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.297
_shelx_estimated_absorpt_T_min   0.943
_shelx_estimated_absorpt_T_max   0.971
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(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            20598
_diffrn_reflns_av_unetI/netI     0.0899
_diffrn_reflns_av_R_equivalents  0.1192
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.163
_diffrn_reflns_theta_max         27.474
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             10117
_reflns_number_gt                7811
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.1000P)²+2.5000P] 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         10117
_refine_ls_number_parameters     577
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0884
_refine_ls_R_factor_gt           0.0691
_refine_ls_wR_factor_ref         0.2030
_refine_ls_wR_factor_gt          0.1813
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      1.000
_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 0.94685(8) 0.82259(8) 0.54880(9) 0.0607(3) Uani 1 1 d . . . . .
S1 S 0.40434(6) 0.61424(6) 0.37954(4) 0.02541(17) Uani 1 1 d . . . . .
O1 O 0.55739(18) 0.73241(18) 0.25939(14) 0.0336(5) Uani 1 1 d . . . . .
O2 O 0.47935(18) 0.75034(18) 0.13907(14) 0.0346(5) Uani 1 1 d . . . . .
O3 O 0.2468(2) 0.5897(2) 0.29721(16) 0.0455(6) Uani 1 1 d . . . . .
O4 O 0.3096(2) 0.6500(2) 0.15612(15) 0.0398(5) Uani 1 1 d . . . . .
N1 N 0.5809(2) 0.6769(2) 0.46401(17) 0.0285(5) Uani 1 1 d . . . . .
C1 C 0.6216(2) 0.5781(2) 0.42214(18) 0.0260(5) Uani 1 1 d . . . . .
C2 C 0.7388(2) 0.5097(3) 0.4171(2) 0.0315(6) Uani 1 1 d . . . . .
H2A H 0.7886 0.5322 0.4412 0.038 Uiso 1 1 calc R U . . .
C3 C 0.7809(3) 0.4105(3) 0.3773(2) 0.0346(7) Uani 1 1 d . . . . .
H3A H 0.8588 0.3676 0.3742 0.042 Uiso 1 1 calc R U . . .
C4 C 0.7078(3) 0.3736(3) 0.3416(2) 0.0368(7) Uani 1 1 d . . . . .
H4A H 0.7362 0.3063 0.3152 0.044 Uiso 1 1 calc R U . . .
C5 C 0.5940(3) 0.4379(2) 0.3462(2) 0.0311(6) Uani 1 1 d . . . . .
H5A H 0.5446 0.4137 0.3232 0.037 Uiso 1 1 calc R U . . .
C6 C 0.5508(2) 0.5393(2) 0.38487(18) 0.0261(5) Uani 1 1 d . . . . .
C7 C 0.3778(2) 0.7255(2) 0.44542(18) 0.0262(5) Uani 1 1 d . . . . .
C8 C 0.2620(3) 0.7925(3) 0.4651(2) 0.0337(6) Uani 1 1 d . . . . .
H8A H 0.2061 0.7775 0.4425 0.040 Uiso 1 1 calc R U . . .
C9 C 0.2287(3) 0.8800(3) 0.5172(2) 0.0383(7) Uani 1 1 d . . . . .
H9A H 0.1512 0.9254 0.5293 0.046 Uiso 1 1 calc R U . . .
C10 C 0.3127(3) 0.9000(3) 0.5519(2) 0.0368(7) Uani 1 1 d . . . . .
H10A H 0.2909 0.9590 0.5879 0.044 Uiso 1 1 calc R U . . .
C11 C 0.4274(3) 0.8338(3) 0.5337(2) 0.0337(6) Uani 1 1 d . . . . .
H11A H 0.4819 0.8486 0.5581 0.040 Uiso 1 1 calc R U . . .
C12 C 0.4645(2) 0.7444(2) 0.47931(18) 0.0267(5) Uani 1 1 d . . . . .
C13 C 0.6665(2) 0.7153(2) 0.4873(2) 0.0282(6) Uani 1 1 d . . . . .
C14 C 0.7285(3) 0.7710(3) 0.4207(2) 0.0318(6) Uani 1 1 d . . . . .
H14A H 0.7128 0.7851 0.3637 0.038 Uiso 1 1 calc R U . . .
C15 C 0.8146(3) 0.8056(3) 0.4404(2) 0.0372(7) Uani 1 1 d . . . . .
H15A H 0.8578 0.8426 0.3968 0.045 Uiso 1 1 calc R U . . .
C16 C 0.8346(3) 0.7838(2) 0.5256(2) 0.0367(7) Uani 1 1 d . . . . .
C17 C 0.7712(3) 0.7318(3) 0.5926(2) 0.0396(7) Uani 1 1 d . . . . .
H17A H 0.7855 0.7198 0.6500 0.047 Uiso 1 1 calc R U . . .
C18 C 0.6850(3) 0.6974(3) 0.5729(2) 0.0358(7) Uani 1 1 d . . . . .
H18A H 0.6403 0.6625 0.6173 0.043 Uiso 1 1 calc R U . . .
C19 C 0.4004(2) 0.6630(2) 0.27091(18) 0.0259(5) Uani 1 1 d . . . . .
C20 C 0.4853(2) 0.7179(2) 0.22442(19) 0.0269(6) Uani 1 1 d . . . . .
C21 C 0.5680(3) 0.7990(3) 0.0872(2) 0.0420(8) Uani 1 1 d . . . . .
H21A H 0.6457 0.7462 0.0838 0.050 Uiso 1 1 calc R U . . .
H21B H 0.5642 0.8635 0.1151 0.050 Uiso 1 1 calc R U . . .
C22 C 0.5438(4) 0.8310(4) -0.0047(3) 0.0611(12) Uani 1 1 d . . . . .
H22A H 0.6012 0.8636 -0.0407 0.092 Uiso 1 1 calc R U . . .
H22B H 0.5479 0.7666 -0.0317 0.092 Uiso 1 1 calc R U . . .
H22C H 0.4667 0.8834 -0.0005 0.092 Uiso 1 1 calc R U . . .
C23 C 0.3186(2) 0.6348(2) 0.23316(19) 0.0271(6) Uani 1 1 d . . . . .
C24 C 0.1788(3) 0.5344(3) 0.2687(3) 0.0468(9) Uani 1 1 d . . . . .
H24A H 0.2245 0.4580 0.2583 0.056 Uiso 1 1 calc R U . . .
H24B H 0.1568 0.5701 0.2133 0.056 Uiso 1 1 calc R U . . .
C25 C 0.0722(4) 0.5400(4) 0.3405(3) 0.0637(12) Uani 1 1 d . . . . .
H25A H 0.0252 0.5037 0.3231 0.096 Uiso 1 1 calc R U . . .
H25B H 0.0949 0.5042 0.3948 0.096 Uiso 1 1 calc R U . . .
H25C H 0.0274 0.6159 0.3500 0.096 Uiso 1 1 calc R U . . .
Cl2 Cl 0.03598(9) 1.61746(7) 0.84571(6) 0.0519(3) Uani 1 1 d . . . . .
S2 S 0.19201(6) 0.88297(5) 0.87387(5) 0.02782(17) Uani 1 1 d . . . . .
O5 O 0.31377(19) 1.04067(18) 0.77225(17) 0.0395(5) Uani 1 1 d . . . . .
O6 O 0.48282(18) 0.91321(18) 0.71448(15) 0.0367(5) Uani 1 1 d . . . . .
O7 O 0.5050(2) 0.69928(18) 0.77319(17) 0.0423(6) Uani 1 1 d . . . . .
O8 O 0.3501(2) 0.67668(18) 0.87582(16) 0.0407(5) Uani 1 1 d . . . . .
N2 N 0.0834(2) 1.13998(19) 0.89173(15) 0.0265(5) Uani 1 1 d . . . . .
C26 C 0.1372(2) 1.0774(2) 0.95909(18) 0.0254(5) Uani 1 1 d . . . . .
C27 C 0.1459(3) 1.1298(3) 1.0304(2) 0.0318(6) Uani 1 1 d . . . . .
H27A H 0.1200 1.2064 1.0302 0.038 Uiso 1 1 calc R U . . .
C28 C 0.1925(3) 1.0680(3) 1.1003(2) 0.0356(7) Uani 1 1 d . . . . .
H28A H 0.1977 1.1040 1.1466 0.043 Uiso 1 1 calc R U . . .
C29 C 0.2315(3) 0.9544(3) 1.1036(2) 0.0363(7) Uani 1 1 d . . . . .
H29A H 0.2620 0.9141 1.1516 0.044 Uiso 1 1 calc R U . . .
C30 C 0.2247(2) 0.9012(3) 1.0346(2) 0.0319(6) Uani 1 1 d . . . . .
H30A H 0.2503 0.8245 1.0359 0.038 Uiso 1 1 calc R U . . .
C31 C 0.1794(2) 0.9625(2) 0.96283(19) 0.0272(6) Uani 1 1 d . . . . .
C32 C 0.0943(2) 0.9810(2) 0.81460(19) 0.0280(6) Uani 1 1 d . . . . .
C33 C 0.0579(3) 0.9387(3) 0.7524(2) 0.0347(7) Uani 1 1 d . . . . .
H33A H 0.0840 0.8631 0.7455 0.042 Uiso 1 1 calc R U . . .
C34 C -0.0170(3) 1.0088(3) 0.7009(2) 0.0382(7) Uani 1 1 d . . . . .
H34A H -0.0412 0.9808 0.6593 0.046 Uiso 1 1 calc R U . . .
C35 C -0.0554(3) 1.1211(3) 0.7123(2) 0.0360(7) Uani 1 1 d . . . . .
H35A H -0.1050 1.1688 0.6776 0.043 Uiso 1 1 calc R U . . .
C36 C -0.0210(3) 1.1630(3) 0.7742(2) 0.0319(6) Uani 1 1 d . . . . .
H36A H -0.0485 1.2386 0.7811 0.038 Uiso 1 1 calc R U . . .
C37 C 0.0547(2) 1.0939(2) 0.82746(18) 0.0260(5) Uani 1 1 d . . . . .
C38 C 0.0709(2) 1.2563(2) 0.88164(19) 0.0265(5) Uani 1 1 d . . . . .
C39 C 0.1627(3) 1.2905(2) 0.82913(19) 0.0297(6) Uani 1 1 d . . . . .
H39A H 0.2307 1.2387 0.8010 0.036 Uiso 1 1 calc R U . . .
C40 C 0.1539(3) 1.4019(2) 0.8181(2) 0.0331(6) Uani 1 1 d . . . . .
H40A H 0.2156 1.4254 0.7832 0.040 Uiso 1 1 calc R U . . .
C41 C 0.0509(3) 1.4774(2) 0.8603(2) 0.0339(6) Uani 1 1 d . . . . .
C42 C -0.0410(3) 1.4435(3) 0.9134(2) 0.0355(7) Uani 1 1 d . . . . .
H42A H -0.1092 1.4951 0.9414 0.043 Uiso 1 1 calc R U . . .
C43 C -0.0306(3) 1.3319(2) 0.9246(2) 0.0319(6) Uani 1 1 d . . . . .
H43A H -0.0915 1.3081 0.9607 0.038 Uiso 1 1 calc R U . . .
C44 C 0.3323(2) 0.8529(2) 0.8091(2) 0.0288(6) Uani 1 1 d . . . . .
C45 C 0.3731(2) 0.9441(2) 0.76539(19) 0.0278(6) Uani 1 1 d . . . . .
C46 C 0.5351(3) 0.9984(3) 0.6743(2) 0.0384(7) Uani 1 1 d . . . . .
H46A H 0.4753 1.0700 0.6796 0.046 Uiso 1 1 calc R U . . .
H46B H 0.5683 0.9872 0.6112 0.046 Uiso 1 1 calc R U . . .
C47 C 0.6288(3) 0.9956(3) 0.7198(3) 0.0514(9) Uani 1 1 d . . . . .
H47A H 0.6632 1.0525 0.6928 0.077 Uiso 1 1 calc R U . . .
H47B H 0.5955 1.0076 0.7821 0.077 Uiso 1 1 calc R U . . .
H47C H 0.6883 0.9250 0.7138 0.077 Uiso 1 1 calc R U . . .
C48 C 0.4053(3) 0.7393(2) 0.8151(2) 0.0299(6) Uani 1 1 d . . . . .
C49 C 0.4188(3) 0.5636(3) 0.8907(3) 0.0460(8) Uani 1 1 d . . . . .
H49A H 0.4871 0.5607 0.9123 0.055 Uiso 1 1 calc R U . . .
H49B H 0.4457 0.5263 0.8352 0.055 Uiso 1 1 calc R U . . .
C50 C 0.3432(4) 0.5091(3) 0.9581(3) 0.0501(9) Uani 1 1 d . . . . .
H50A H 0.3870 0.4334 0.9693 0.075 Uiso 1 1 calc R U . . .
H50B H 0.3174 0.5464 1.0128 0.075 Uiso 1 1 calc R U . . .
H50C H 0.2762 0.5122 0.9360 0.075 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 C16 1.749(3) . ?
S1 C19 1.715(3) . ?
S1 C6 1.764(3) . ?
S1 C7 1.766(3) . ?
O1 C20 1.226(3) . ?
O2 C20 1.340(3) . ?
O2 C21 1.451(4) . ?
O3 C23 1.358(4) . ?
O3 C24 1.442(4) . ?
O4 C23 1.207(3) . ?
N1 C1 1.389(4) . ?
N1 C12 1.393(3) . ?
N1 C13 1.441(3) . ?
C1 C6 1.403(4) . ?
C1 C2 1.413(4) . ?
C2 C3 1.376(4) . ?
C2 H2A 0.9300 . ?
C3 C4 1.399(5) . ?
C3 H3A 0.9300 . ?
C4 C5 1.365(4) . ?
C4 H4A 0.9300 . ?
C5 C6 1.393(4) . ?
C5 H5A 0.9300 . ?
C7 C8 1.386(4) . ?
C7 C12 1.404(4) . ?
C8 C9 1.366(5) . ?
C8 H8A 0.9300 . ?
C9 C10 1.387(5) . ?
C9 H9A 0.9300 . ?
C10 C11 1.372(4) . ?
C10 H10A 0.9300 . ?
C11 C12 1.403(4) . ?
C11 H11A 0.9300 . ?
C13 C18 1.375(4) . ?
C13 C14 1.387(4) . ?
C14 C15 1.392(4) . ?
C14 H14A 0.9300 . ?
C15 C16 1.374(5) . ?
C15 H15A 0.9300 . ?
C16 C17 1.371(5) . ?
C17 C18 1.391(4) . ?
C17 H17A 0.9300 . ?
C18 H18A 0.9300 . ?
C19 C20 1.444(4) . ?
C19 C23 1.446(4) . ?
C21 C22 1.498(5) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C24 C25 1.483(6) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
Cl2 C41 1.736(3) . ?
S2 C44 1.718(3) . ?
S2 C32 1.764(3) . ?
S2 C31 1.772(3) . ?
O5 C45 1.219(4) . ?
O6 C45 1.346(3) . ?
O6 C46 1.442(4) . ?
O7 C48 1.214(4) . ?
O8 C48 1.352(4) . ?
O8 C49 1.441(4) . ?
N2 C26 1.391(3) . ?
N2 C37 1.395(4) . ?
N2 C38 1.442(4) . ?
C26 C31 1.394(4) . ?
C26 C27 1.412(4) . ?
C27 C28 1.379(4) . ?
C27 H27A 0.9300 . ?
C28 C29 1.376(5) . ?
C28 H28A 0.9300 . ?
C29 C30 1.378(5) . ?
C29 H29A 0.9300 . ?
C30 C31 1.393(4) . ?
C30 H30A 0.9300 . ?
C32 C37 1.396(4) . ?
C32 C33 1.396(4) . ?
C33 C34 1.386(5) . ?
C33 H33A 0.9300 . ?
C34 C35 1.385(5) . ?
C34 H34A 0.9300 . ?
C35 C36 1.372(4) . ?
C35 H35A 0.9300 . ?
C36 C37 1.406(4) . ?
C36 H36A 0.9300 . ?
C38 C39 1.381(4) . ?
C38 C43 1.384(4) . ?
C39 C40 1.391(4) . ?
C39 H39A 0.9300 . ?
C40 C41 1.389(4) . ?
C40 H40A 0.9300 . ?
C41 C42 1.384(5) . ?
C42 C43 1.388(4) . ?
C42 H42A 0.9300 . ?
C43 H43A 0.9300 . ?
C44 C45 1.444(4) . ?
C44 C48 1.446(4) . ?
C46 C47 1.488(5) . ?
C46 H46A 0.9700 . ?
C46 H46B 0.9700 . ?
C47 H47A 0.9600 . ?
C47 H47B 0.9600 . ?
C47 H47C 0.9600 . ?
C49 C50 1.480(5) . ?
C49 H49A 0.9700 . ?
C49 H49B 0.9700 . ?
C50 H50A 0.9600 . ?
C50 H50B 0.9600 . ?
C50 H50C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C19 S1 C6 108.70(13) . . ?
C19 S1 C7 109.45(13) . . ?
C6 S1 C7 100.92(13) . . ?
C20 O2 C21 116.4(2) . . ?
C23 O3 C24 118.0(3) . . ?
C1 N1 C12 124.2(2) . . ?
C1 N1 C13 117.5(2) . . ?
C12 N1 C13 118.1(2) . . ?
N1 C1 C6 123.2(2) . . ?
N1 C1 C2 120.2(2) . . ?
C6 C1 C2 116.5(3) . . ?
C3 C2 C1 121.5(3) . . ?
C3 C2 H2A 119.3 . . ?
C1 C2 H2A 119.3 . . ?
C2 C3 C4 120.6(3) . . ?
C2 C3 H3A 119.7 . . ?
C4 C3 H3A 119.7 . . ?
C5 C4 C3 118.9(3) . . ?
C5 C4 H4A 120.6 . . ?
C3 C4 H4A 120.6 . . ?
C4 C5 C6 121.1(3) . . ?
C4 C5 H5A 119.5 . . ?
C6 C5 H5A 119.5 . . ?
C5 C6 C1 121.4(3) . . ?
C5 C6 S1 114.7(2) . . ?
C1 C6 S1 123.9(2) . . ?
C8 C7 C12 121.2(3) . . ?
C8 C7 S1 114.9(2) . . ?
C12 C7 S1 123.8(2) . . ?
C9 C8 C7 121.0(3) . . ?
C9 C8 H8A 119.5 . . ?
C7 C8 H8A 119.5 . . ?
C8 C9 C10 118.8(3) . . ?
C8 C9 H9A 120.6 . . ?
C10 C9 H9A 120.6 . . ?
C11 C10 C9 120.8(3) . . ?
C11 C10 H10A 119.6 . . ?
C9 C10 H10A 119.6 . . ?
C10 C11 C12 121.7(3) . . ?
C10 C11 H11A 119.2 . . ?
C12 C11 H11A 119.2 . . ?
N1 C12 C11 120.3(3) . . ?
N1 C12 C7 123.1(2) . . ?
C11 C12 C7 116.5(3) . . ?
C18 C13 C14 121.5(3) . . ?
C18 C13 N1 120.8(3) . . ?
C14 C13 N1 117.8(3) . . ?
C13 C14 C15 119.0(3) . . ?
C13 C14 H14A 120.5 . . ?
C15 C14 H14A 120.5 . . ?
C16 C15 C14 118.7(3) . . ?
C16 C15 H15A 120.6 . . ?
C14 C15 H15A 120.6 . . ?
C17 C16 C15 122.7(3) . . ?
C17 C16 Cl1 118.8(3) . . ?
C15 C16 Cl1 118.5(3) . . ?
C16 C17 C18 118.6(3) . . ?
C16 C17 H17A 120.7 . . ?
C18 C17 H17A 120.7 . . ?
C13 C18 C17 119.5(3) . . ?
C13 C18 H18A 120.3 . . ?
C17 C18 H18A 120.3 . . ?
C20 C19 C23 126.8(2) . . ?
C20 C19 S1 117.5(2) . . ?
C23 C19 S1 115.4(2) . . ?
O1 C20 O2 122.8(3) . . ?
O1 C20 C19 123.1(3) . . ?
O2 C20 C19 114.0(2) . . ?
O2 C21 C22 107.5(3) . . ?
O2 C21 H21A 110.2 . . ?
C22 C21 H21A 110.2 . . ?
O2 C21 H21B 110.2 . . ?
C22 C21 H21B 110.2 . . ?
H21A C21 H21B 108.5 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O4 C23 O3 121.9(3) . . ?
O4 C23 C19 126.9(3) . . ?
O3 C23 C19 111.1(2) . . ?
O3 C24 C25 107.8(3) . . ?
O3 C24 H24A 110.2 . . ?
C25 C24 H24A 110.2 . . ?
O3 C24 H24B 110.2 . . ?
C25 C24 H24B 110.2 . . ?
H24A C24 H24B 108.5 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C44 S2 C32 109.43(14) . . ?
C44 S2 C31 109.47(13) . . ?
C32 S2 C31 99.71(13) . . ?
C45 O6 C46 118.0(2) . . ?
C48 O8 C49 116.0(2) . . ?
C26 N2 C37 123.2(2) . . ?
C26 N2 C38 117.6(2) . . ?
C37 N2 C38 118.7(2) . . ?
N2 C26 C31 123.0(2) . . ?
N2 C26 C27 120.0(2) . . ?
C31 C26 C27 116.8(3) . . ?
C28 C27 C26 120.4(3) . . ?
C28 C27 H27A 119.8 . . ?
C26 C27 H27A 119.8 . . ?
C29 C28 C27 121.8(3) . . ?
C29 C28 H28A 119.1 . . ?
C27 C28 H28A 119.1 . . ?
C28 C29 C30 119.0(3) . . ?
C28 C29 H29A 120.5 . . ?
C30 C29 H29A 120.5 . . ?
C29 C30 C31 120.0(3) . . ?
C29 C30 H30A 120.0 . . ?
C31 C30 H30A 120.0 . . ?
C30 C31 C26 122.0(3) . . ?
C30 C31 S2 114.4(2) . . ?
C26 C31 S2 123.4(2) . . ?
C37 C32 C33 121.0(3) . . ?
C37 C32 S2 123.4(2) . . ?
C33 C32 S2 115.6(2) . . ?
C34 C33 C32 120.4(3) . . ?
C34 C33 H33A 119.8 . . ?
C32 C33 H33A 119.8 . . ?
C35 C34 C33 119.0(3) . . ?
C35 C34 H34A 120.5 . . ?
C33 C34 H34A 120.5 . . ?
C36 C35 C34 120.9(3) . . ?
C36 C35 H35A 119.6 . . ?
C34 C35 H35A 119.6 . . ?
C35 C36 C37 121.4(3) . . ?
C35 C36 H36A 119.3 . . ?
C37 C36 H36A 119.3 . . ?
N2 C37 C32 123.5(2) . . ?
N2 C37 C36 119.1(3) . . ?
C32 C37 C36 117.4(3) . . ?
C39 C38 C43 120.8(3) . . ?
C39 C38 N2 118.7(2) . . ?
C43 C38 N2 120.6(3) . . ?
C38 C39 C40 120.3(3) . . ?
C38 C39 H39A 119.9 . . ?
C40 C39 H39A 119.9 . . ?
C41 C40 C39 118.6(3) . . ?
C41 C40 H40A 120.7 . . ?
C39 C40 H40A 120.7 . . ?
C42 C41 C40 121.3(3) . . ?
C42 C41 Cl2 119.0(2) . . ?
C40 C41 Cl2 119.7(2) . . ?
C41 C42 C43 119.5(3) . . ?
C41 C42 H42A 120.2 . . ?
C43 C42 H42A 120.2 . . ?
C38 C43 C42 119.5(3) . . ?
C38 C43 H43A 120.2 . . ?
C42 C43 H43A 120.2 . . ?
C45 C44 C48 125.2(3) . . ?
C45 C44 S2 117.8(2) . . ?
C48 C44 S2 116.2(2) . . ?
O5 C45 O6 122.4(3) . . ?
O5 C45 C44 123.7(3) . . ?
O6 C45 C44 113.9(2) . . ?
O6 C46 C47 109.9(3) . . ?
O6 C46 H46A 109.7 . . ?
C47 C46 H46A 109.7 . . ?
O6 C46 H46B 109.7 . . ?
C47 C46 H46B 109.7 . . ?
H46A C46 H46B 108.2 . . ?
C46 C47 H47A 109.5 . . ?
C46 C47 H47B 109.5 . . ?
H47A C47 H47B 109.5 . . ?
C46 C47 H47C 109.5 . . ?
H47A C47 H47C 109.5 . . ?
H47B C47 H47C 109.5 . . ?
O7 C48 O8 120.8(3) . . ?
O7 C48 C44 127.2(3) . . ?
O8 C48 C44 112.0(2) . . ?
O8 C49 C50 107.8(3) . . ?
O8 C49 H49A 110.2 . . ?
C50 C49 H49A 110.2 . . ?
O8 C49 H49B 110.2 . . ?
C50 C49 H49B 110.2 . . ?
H49A C49 H49B 108.5 . . ?
C49 C50 H50A 109.5 . . ?
C49 C50 H50B 109.5 . . ?
H50A C50 H50B 109.5 . . ?
C49 C50 H50C 109.5 . . ?
H50A C50 H50C 109.5 . . ?
H50B C50 H50C 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
C12 N1 C1 C6 4.7(4) . . . . ?
C13 N1 C1 C6 -170.8(3) . . . . ?
C12 N1 C1 C2 -173.9(3) . . . . ?
C13 N1 C1 C2 10.6(4) . . . . ?
N1 C1 C2 C3 178.9(3) . . . . ?
C6 C1 C2 C3 0.2(4) . . . . ?
C1 C2 C3 C4 -0.9(5) . . . . ?
C2 C3 C4 C5 0.5(5) . . . . ?
C3 C4 C5 C6 0.6(5) . . . . ?
C4 C5 C6 C1 -1.3(4) . . . . ?
C4 C5 C6 S1 176.8(2) . . . . ?
N1 C1 C6 C5 -177.7(3) . . . . ?
C2 C1 C6 C5 0.9(4) . . . . ?
N1 C1 C6 S1 4.3(4) . . . . ?
C2 C1 C6 S1 -177.1(2) . . . . ?
C19 S1 C6 C5 -71.6(2) . . . . ?
C7 S1 C6 C5 173.3(2) . . . . ?
C19 S1 C6 C1 106.5(3) . . . . ?
C7 S1 C6 C1 -8.6(3) . . . . ?
C19 S1 C7 C8 74.4(2) . . . . ?
C6 S1 C7 C8 -171.1(2) . . . . ?
C19 S1 C7 C12 -108.0(3) . . . . ?
C6 S1 C7 C12 6.5(3) . . . . ?
C12 C7 C8 C9 0.9(5) . . . . ?
S1 C7 C8 C9 178.5(3) . . . . ?
C7 C8 C9 C10 -1.2(5) . . . . ?
C8 C9 C10 C11 0.5(5) . . . . ?
C9 C10 C11 C12 0.5(5) . . . . ?
C1 N1 C12 C11 170.4(3) . . . . ?
C13 N1 C12 C11 -14.2(4) . . . . ?
C1 N1 C12 C7 -7.0(4) . . . . ?
C13 N1 C12 C7 168.5(3) . . . . ?
C10 C11 C12 N1 -178.3(3) . . . . ?
C10 C11 C12 C7 -0.8(5) . . . . ?
C8 C7 C12 N1 177.6(3) . . . . ?
S1 C7 C12 N1 0.2(4) . . . . ?
C8 C7 C12 C11 0.1(4) . . . . ?
S1 C7 C12 C11 -177.3(2) . . . . ?
C1 N1 C13 C18 -98.5(3) . . . . ?
C12 N1 C13 C18 85.7(4) . . . . ?
C1 N1 C13 C14 81.8(3) . . . . ?
C12 N1 C13 C14 -94.0(3) . . . . ?
C18 C13 C14 C15 2.6(5) . . . . ?
N1 C13 C14 C15 -177.7(3) . . . . ?
C13 C14 C15 C16 -0.5(5) . . . . ?
C14 C15 C16 C17 -1.6(5) . . . . ?
C14 C15 C16 Cl1 177.5(2) . . . . ?
C15 C16 C17 C18 1.5(5) . . . . ?
Cl1 C16 C17 C18 -177.6(3) . . . . ?
C14 C13 C18 C17 -2.7(5) . . . . ?
N1 C13 C18 C17 177.7(3) . . . . ?
C16 C17 C18 C13 0.6(5) . . . . ?
C6 S1 C19 C20 -48.3(3) . . . . ?
C7 S1 C19 C20 61.1(2) . . . . ?
C6 S1 C19 C23 126.1(2) . . . . ?
C7 S1 C19 C23 -124.5(2) . . . . ?
C21 O2 C20 O1 3.3(4) . . . . ?
C21 O2 C20 C19 -175.8(3) . . . . ?
C23 C19 C20 O1 -174.9(3) . . . . ?
S1 C19 C20 O1 -1.2(4) . . . . ?
C23 C19 C20 O2 4.3(4) . . . . ?
S1 C19 C20 O2 177.9(2) . . . . ?
C20 O2 C21 C22 -178.9(3) . . . . ?
C24 O3 C23 O4 15.5(4) . . . . ?
C24 O3 C23 C19 -166.1(3) . . . . ?
C20 C19 C23 O4 2.0(5) . . . . ?
S1 C19 C23 O4 -171.7(3) . . . . ?
C20 C19 C23 O3 -176.3(3) . . . . ?
S1 C19 C23 O3 10.0(3) . . . . ?
C23 O3 C24 C25 -153.5(3) . . . . ?
C37 N2 C26 C31 7.4(4) . . . . ?
C38 N2 C26 C31 -164.4(3) . . . . ?
C37 N2 C26 C27 -169.4(3) . . . . ?
C38 N2 C26 C27 18.8(4) . . . . ?
N2 C26 C27 C28 175.9(3) . . . . ?
C31 C26 C27 C28 -1.1(4) . . . . ?
C26 C27 C28 C29 -0.2(5) . . . . ?
C27 C28 C29 C30 0.6(5) . . . . ?
C28 C29 C30 C31 0.3(4) . . . . ?
C29 C30 C31 C26 -1.7(4) . . . . ?
C29 C30 C31 S2 173.1(2) . . . . ?
N2 C26 C31 C30 -174.9(3) . . . . ?
C27 C26 C31 C30 2.0(4) . . . . ?
N2 C26 C31 S2 10.8(4) . . . . ?
C27 C26 C31 S2 -172.4(2) . . . . ?
C44 S2 C31 C30 -79.8(2) . . . . ?
C32 S2 C31 C30 165.4(2) . . . . ?
C44 S2 C31 C26 94.9(3) . . . . ?
C32 S2 C31 C26 -19.8(3) . . . . ?
C44 S2 C32 C37 -98.4(3) . . . . ?
C31 S2 C32 C37 16.3(3) . . . . ?
C44 S2 C32 C33 81.4(2) . . . . ?
C31 S2 C32 C33 -163.9(2) . . . . ?
C37 C32 C33 C34 1.1(4) . . . . ?
S2 C32 C33 C34 -178.7(2) . . . . ?
C32 C33 C34 C35 -0.2(5) . . . . ?
C33 C34 C35 C36 -0.6(5) . . . . ?
C34 C35 C36 C37 0.5(5) . . . . ?
C26 N2 C37 C32 -11.2(4) . . . . ?
C38 N2 C37 C32 160.5(3) . . . . ?
C26 N2 C37 C36 166.6(3) . . . . ?
C38 N2 C37 C36 -21.7(4) . . . . ?
C33 C32 C37 N2 176.6(3) . . . . ?
S2 C32 C37 N2 -3.5(4) . . . . ?
C33 C32 C37 C36 -1.2(4) . . . . ?
S2 C32 C37 C36 178.6(2) . . . . ?
C35 C36 C37 N2 -177.6(3) . . . . ?
C35 C36 C37 C32 0.4(4) . . . . ?
C26 N2 C38 C39 86.4(3) . . . . ?
C37 N2 C38 C39 -85.8(3) . . . . ?
C26 N2 C38 C43 -92.9(3) . . . . ?
C37 N2 C38 C43 94.9(3) . . . . ?
C43 C38 C39 C40 -0.5(4) . . . . ?
N2 C38 C39 C40 -179.8(3) . . . . ?
C38 C39 C40 C41 -0.5(4) . . . . ?
C39 C40 C41 C42 0.9(5) . . . . ?
C39 C40 C41 Cl2 -178.5(2) . . . . ?
C40 C41 C42 C43 -0.3(5) . . . . ?
Cl2 C41 C42 C43 179.1(2) . . . . ?
C39 C38 C43 C42 1.1(4) . . . . ?
N2 C38 C43 C42 -179.6(3) . . . . ?
C41 C42 C43 C38 -0.7(5) . . . . ?
C32 S2 C44 C45 47.2(3) . . . . ?
C31 S2 C44 C45 -61.2(3) . . . . ?
C32 S2 C44 C48 -142.6(2) . . . . ?
C31 S2 C44 C48 109.1(2) . . . . ?
C46 O6 C45 O5 6.3(4) . . . . ?
C46 O6 C45 C44 -174.8(3) . . . . ?
C48 C44 C45 O5 -169.0(3) . . . . ?
S2 C44 C45 O5 0.3(4) . . . . ?
C48 C44 C45 O6 12.1(4) . . . . ?
S2 C44 C45 O6 -178.6(2) . . . . ?
C45 O6 C46 C47 108.2(3) . . . . ?
C49 O8 C48 O7 3.5(4) . . . . ?
C49 O8 C48 C44 -176.1(3) . . . . ?
C45 C44 C48 O7 -13.3(5) . . . . ?
S2 C44 C48 O7 177.2(3) . . . . ?
C45 C44 C48 O8 166.2(3) . . . . ?
S2 C44 C48 O8 -3.2(3) . . . . ?
C48 O8 C49 C50 -179.5(3) . . . . ?

_refine_diff_density_max         1.312
_refine_diff_density_min         -0.564
_refine_diff_density_rms         0.088

