# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2022

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1946891'
loop_
_audit_author_name
_audit_author_address
'S Athimoolam'
;University College of Engineering, Anna University Constituent College, Nagercoil 
India
;
_audit_update_record             
;
2019-08-13 deposited with the CCDC.	2021-12-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
SPIRO
;
_chemical_name_common            SPIRO
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H19 N5 O4 S'
_chemical_formula_sum            'C16 H19 N5 O4 S'
_chemical_formula_weight         377.42

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   26.46(4)
_cell_length_b                   6.552(10)
_cell_length_c                   20.28(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.62(2)
_cell_angle_gamma                90
_cell_volume                     3504(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2243
_cell_measurement_theta_min      3.42
_cell_measurement_theta_max      26.41

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    none
_exptl_crystal_density_diffrn    1.431
_exptl_crystal_F_000             1584
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    0.218
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6757

_exptl_special_details           
;
 The following wavelength and cell were deduced by SADABS from the
 direction cosines etc. They are given here for emergency use only:
 CELL 0.71073   26.419    6.546   20.107   89.769   94.359   90.038
;


_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14309
_diffrn_reflns_av_unetI/netI     0.0469
_diffrn_reflns_av_R_equivalents  0.0550
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.439
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.970
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.970
_reflns_number_total             3080
_reflns_number_gt                2187
_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       'SMART (Bruker, 2001)'
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2015)'
_computing_structure_refinement  SHELXL-2014
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  SHELXL-2014

_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)+(0.0725P)²+4.3482P] 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         3080
_refine_ls_number_parameters     257
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0821
_refine_ls_R_factor_gt           0.0529
_refine_ls_wR_factor_ref         0.1463
_refine_ls_wR_factor_gt          0.1307
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.069
_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 0.75863(10) 0.1430(5) 0.58556(15) 0.0400(8) Uani 1 1 d . . . . .
C2 C 0.73488(12) -0.0016(5) 0.54378(17) 0.0512(9) Uani 1 1 d . . . . .
H2 H 0.7542 -0.0836 0.5181 0.061 Uiso 1 1 calc R U . . .
C3 C 0.68327(12) -0.0252(5) 0.53986(17) 0.0500(9) Uani 1 1 d . . . . .
H3A H 0.6673 -0.1210 0.5115 0.060 Uiso 1 1 calc R U . . .
C4 C 0.65551(11) 0.0979(5) 0.57947(15) 0.0418(8) Uani 1 1 d . . . . .
H4 H 0.6205 0.0808 0.5776 0.050 Uiso 1 1 calc R U . . .
C5 C 0.67728(9) 0.2433(4) 0.62111(13) 0.0313(7) Uani 1 1 d . . . . .
C6 C 0.64478(9) 0.3690(4) 0.66513(14) 0.0330(7) Uani 1 1 d . . . . .
C7 C 0.67656(10) 0.4736(5) 0.72202(15) 0.0396(7) Uani 1 1 d . . . . .
H7A H 0.6561 0.5750 0.7424 0.048 Uiso 1 1 calc R U . . .
H7B H 0.6874 0.3733 0.7554 0.048 Uiso 1 1 calc R U . . .
C8 C 0.73118(9) 0.2774(4) 0.62450(14) 0.0321(7) Uani 1 1 d . . . . .
C9 C 0.55202(10) 0.4589(5) 0.63534(16) 0.0382(7) Uani 1 1 d . . . . .
C10 C 0.61336(10) 0.0690(5) 0.72620(15) 0.0377(7) Uani 1 1 d . . . . .
C11 C 0.56891(12) -0.0527(5) 0.74473(18) 0.0493(9) Uani 1 1 d . . . . .
H11A H 0.5491 -0.0949 0.7054 0.074 Uiso 1 1 calc R U . . .
H11B H 0.5484 0.0295 0.7713 0.074 Uiso 1 1 calc R U . . .
H11C H 0.5806 -0.1709 0.7694 0.074 Uiso 1 1 calc R U . . .
C13 C 0.50165(11) 0.7086(5) 0.57203(16) 0.0424(8) Uani 1 1 d . . . . .
C14 C 0.45076(11) 0.7739(6) 0.5406(2) 0.0625(11) Uani 1 1 d . . . . .
H14A H 0.4551 0.8853 0.5109 0.094 Uiso 1 1 calc R U . . .
H14B H 0.4296 0.8167 0.5744 0.094 Uiso 1 1 calc R U . . .
H14C H 0.4350 0.6615 0.5166 0.094 Uiso 1 1 calc R U . . .
C16 C 0.72223(11) 0.5747(5) 0.69665(17) 0.0462(8) Uani 1 1 d . . . . .
H16A H 0.7114 0.6829 0.6661 0.055 Uiso 1 1 calc R U . . .
H16B H 0.7429 0.6350 0.7333 0.055 Uiso 1 1 calc R U . . .
N1 N 0.81353(10) 0.1493(5) 0.58700(15) 0.0560(8) Uani 1 1 d . . . . .
N2 N 0.60370(7) 0.2425(4) 0.68979(12) 0.0366(6) Uani 1 1 d . . . . .
N3 N 0.75224(8) 0.4257(4) 0.66313(13) 0.0438(7) Uani 1 1 d . . . . .
H3 H 0.7848 0.4334 0.6684 0.053 Uiso 1 1 calc R U . . .
N4 N 0.55365(8) 0.3002(4) 0.67238(13) 0.0422(7) Uani 1 1 d . . . . .
N5 N 0.50456(8) 0.5345(4) 0.61116(17) 0.0636(10) Uani 1 1 d D . . . .
O1 O 0.83523(10) 0.0330(5) 0.55199(17) 0.0939(11) Uani 1 1 d . . . . .
O2 O 0.83703(8) 0.2763(5) 0.62305(14) 0.0767(9) Uani 1 1 d . . . . .
O3 O 0.65755(7) 0.0188(4) 0.74209(11) 0.0519(6) Uani 1 1 d . . . . .
O4 O 0.53949(8) 0.8064(4) 0.56282(13) 0.0621(7) Uani 1 1 d . . . . .
S1 S 0.60916(2) 0.56629(12) 0.61456(4) 0.0400(3) Uani 1 1 d . . . . .
C12 C 0.4646(2) 0.3845(11) 0.5989(4) 0.068(2) Uani 0.5 1 d D . P A 1
H12A H 0.4778 0.2466 0.5975 0.081 Uiso 0.5 1 calc R U P A 1
H12B H 0.4436 0.4129 0.5585 0.081 Uiso 0.5 1 calc R U P A 1
C12' C 0.46035(19) 0.4563(9) 0.6405(3) 0.0328(16) Uani 0.5 1 d D . P A 2
H12C H 0.4336 0.5581 0.6378 0.039 Uiso 0.5 1 calc R U P A 2
H12D H 0.4688 0.4240 0.6868 0.039 Uiso 0.5 1 calc R U P A 2
C15 C 0.4369(4) 0.4216(16) 0.6595(4) 0.076(3) Uani 0.5 1 d D . P A 1
H15A H 0.4602 0.4108 0.6981 0.113 Uiso 0.5 1 calc R U P A 1
H15B H 0.4105 0.3220 0.6617 0.113 Uiso 0.5 1 calc R U P A 1
H15C H 0.4223 0.5558 0.6574 0.113 Uiso 0.5 1 calc R U P A 1
C15' C 0.4425(2) 0.2654(10) 0.6030(3) 0.0429(16) Uani 0.5 1 d D . P A 2
H15D H 0.4341 0.2989 0.5573 0.064 Uiso 0.5 1 calc R U P A 2
H15E H 0.4131 0.2115 0.6218 0.064 Uiso 0.5 1 calc R U P A 2
H15F H 0.4691 0.1652 0.6062 0.064 Uiso 0.5 1 calc R U 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
C1 C2 1.387(5) . ?
C1 C8 1.421(4) . ?
C1 N1 1.451(4) . ?
C2 C3 1.370(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.389(5) . ?
C3 H3A 0.9300 . ?
C4 C5 1.369(4) . ?
C4 H4 0.9300 . ?
C5 C8 1.440(4) . ?
C5 C6 1.529(4) . ?
C6 N2 1.485(4) . ?
C6 C7 1.533(4) . ?
C6 S1 1.859(3) . ?
C7 C16 1.505(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 N3 1.341(4) . ?
C9 N4 1.281(4) . ?
C9 N5 1.401(4) . ?
C9 S1 1.749(3) . ?
C10 O3 1.232(3) . ?
C10 N2 1.369(4) . ?
C10 C11 1.494(4) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C13 O4 1.216(4) . ?
C13 N5 1.388(4) . ?
C13 C14 1.504(4) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C16 N3 1.460(4) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
N1 O1 1.217(4) . ?
N1 O2 1.241(4) . ?
N2 N4 1.395(3) . ?
N3 H3 0.8600 . ?
N5 C12' 1.448(4) . ?
N5 C12 1.450(5) . ?
C12 C15 1.499(5) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12' C15' 1.519(5) . ?
C12' H12C 0.9700 . ?
C12' H12D 0.9700 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C15' H15D 0.9600 . ?
C15' H15E 0.9600 . ?
C15' H15F 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
C2 C1 C8 122.4(3) . . ?
C2 C1 N1 115.8(3) . . ?
C8 C1 N1 121.8(3) . . ?
C3 C2 C1 120.9(3) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C2 C3 C4 118.1(3) . . ?
C2 C3 H3A 120.9 . . ?
C4 C3 H3A 120.9 . . ?
C5 C4 C3 123.0(3) . . ?
C5 C4 H4 118.5 . . ?
C3 C4 H4 118.5 . . ?
C4 C5 C8 120.2(3) . . ?
C4 C5 C6 120.4(3) . . ?
C8 C5 C6 119.3(2) . . ?
N2 C6 C5 110.9(3) . . ?
N2 C6 C7 111.6(2) . . ?
C5 C6 C7 112.3(2) . . ?
N2 C6 S1 102.79(18) . . ?
C5 C6 S1 109.7(2) . . ?
C7 C6 S1 109.1(2) . . ?
C16 C7 C6 110.3(3) . . ?
C16 C7 H7A 109.6 . . ?
C6 C7 H7A 109.6 . . ?
C16 C7 H7B 109.6 . . ?
C6 C7 H7B 109.6 . . ?
H7A C7 H7B 108.1 . . ?
N3 C8 C1 124.5(3) . . ?
N3 C8 C5 120.2(3) . . ?
C1 C8 C5 115.2(3) . . ?
N4 C9 N5 118.6(3) . . ?
N4 C9 S1 118.6(2) . . ?
N5 C9 S1 122.8(2) . . ?
O3 C10 N2 119.6(3) . . ?
O3 C10 C11 122.8(3) . . ?
N2 C10 C11 117.6(2) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O4 C13 N5 120.8(3) . . ?
O4 C13 C14 120.3(3) . . ?
N5 C13 C14 118.8(3) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N3 C16 C7 110.3(3) . . ?
N3 C16 H16A 109.6 . . ?
C7 C16 H16A 109.6 . . ?
N3 C16 H16B 109.6 . . ?
C7 C16 H16B 109.6 . . ?
H16A C16 H16B 108.1 . . ?
O1 N1 O2 121.7(3) . . ?
O1 N1 C1 119.3(3) . . ?
O2 N1 C1 119.0(3) . . ?
C10 N2 N4 119.6(2) . . ?
C10 N2 C6 122.4(2) . . ?
N4 N2 C6 118.0(2) . . ?
C8 N3 C16 122.7(2) . . ?
C8 N3 H3 118.6 . . ?
C16 N3 H3 118.6 . . ?
C9 N4 N2 110.8(2) . . ?
C13 N5 C9 119.8(2) . . ?
C13 N5 C12' 121.1(3) . . ?
C9 N5 C12' 117.5(4) . . ?
C13 N5 C12 116.9(4) . . ?
C9 N5 C12 116.2(4) . . ?
C9 S1 C6 89.83(16) . . ?
N5 C12 C15 98.5(6) . . ?
N5 C12 H12A 112.1 . . ?
C15 C12 H12A 112.1 . . ?
N5 C12 H12B 112.1 . . ?
C15 C12 H12B 112.1 . . ?
H12A C12 H12B 109.7 . . ?
N5 C12' C15' 108.3(5) . . ?
N5 C12' H12C 110.0 . . ?
C15' C12' H12C 110.0 . . ?
N5 C12' H12D 110.0 . . ?
C15' C12' H12D 110.0 . . ?
H12C C12' H12D 108.4 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C12' C15' H15D 109.5 . . ?
C12' C15' H15E 109.5 . . ?
H15D C15' H15E 109.5 . . ?
C12' C15' H15F 109.5 . . ?
H15D C15' H15F 109.5 . . ?
H15E C15' H15F 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
C8 C1 C2 C3 -2.1(5) . . . . ?
N1 C1 C2 C3 178.1(3) . . . . ?
C1 C2 C3 C4 -0.8(5) . . . . ?
C2 C3 C4 C5 1.1(5) . . . . ?
C3 C4 C5 C8 1.2(5) . . . . ?
C3 C4 C5 C6 -177.9(3) . . . . ?
C4 C5 C6 N2 36.9(4) . . . . ?
C8 C5 C6 N2 -142.3(2) . . . . ?
C4 C5 C6 C7 162.5(3) . . . . ?
C8 C5 C6 C7 -16.7(4) . . . . ?
C4 C5 C6 S1 -76.0(3) . . . . ?
C8 C5 C6 S1 104.8(3) . . . . ?
N2 C6 C7 C16 171.6(2) . . . . ?
C5 C6 C7 C16 46.4(3) . . . . ?
S1 C6 C7 C16 -75.5(3) . . . . ?
C2 C1 C8 N3 -176.7(3) . . . . ?
N1 C1 C8 N3 3.1(5) . . . . ?
C2 C1 C8 C5 4.2(4) . . . . ?
N1 C1 C8 C5 -176.0(3) . . . . ?
C4 C5 C8 N3 177.1(3) . . . . ?
C6 C5 C8 N3 -3.7(4) . . . . ?
C4 C5 C8 C1 -3.8(4) . . . . ?
C6 C5 C8 C1 175.4(2) . . . . ?
C6 C7 C16 N3 -56.7(3) . . . . ?
C2 C1 N1 O1 0.9(5) . . . . ?
C8 C1 N1 O1 -178.9(3) . . . . ?
C2 C1 N1 O2 179.5(3) . . . . ?
C8 C1 N1 O2 -0.3(5) . . . . ?
O3 C10 N2 N4 -179.4(3) . . . . ?
C11 C10 N2 N4 0.9(4) . . . . ?
O3 C10 N2 C6 3.4(4) . . . . ?
C11 C10 N2 C6 -176.3(3) . . . . ?
C5 C6 N2 C10 58.4(3) . . . . ?
C7 C6 N2 C10 -67.6(3) . . . . ?
S1 C6 N2 C10 175.6(2) . . . . ?
C5 C6 N2 N4 -118.8(3) . . . . ?
C7 C6 N2 N4 115.1(3) . . . . ?
S1 C6 N2 N4 -1.7(3) . . . . ?
C1 C8 N3 C16 173.1(3) . . . . ?
C5 C8 N3 C16 -7.9(4) . . . . ?
C7 C16 N3 C8 38.9(4) . . . . ?
N5 C9 N4 N2 177.9(3) . . . . ?
S1 C9 N4 N2 0.2(4) . . . . ?
C10 N2 N4 C9 -176.2(3) . . . . ?
C6 N2 N4 C9 1.1(4) . . . . ?
O4 C13 N5 C9 -6.1(5) . . . . ?
C14 C13 N5 C9 173.5(3) . . . . ?
O4 C13 N5 C12' 159.2(4) . . . . ?
C14 C13 N5 C12' -21.2(6) . . . . ?
O4 C13 N5 C12 -155.5(5) . . . . ?
C14 C13 N5 C12 24.0(6) . . . . ?
N4 C9 N5 C13 178.7(3) . . . . ?
S1 C9 N5 C13 -3.8(5) . . . . ?
N4 C9 N5 C12' 12.9(5) . . . . ?
S1 C9 N5 C12' -169.6(3) . . . . ?
N4 C9 N5 C12 -31.6(6) . . . . ?
S1 C9 N5 C12 145.9(4) . . . . ?
N4 C9 S1 C6 -1.0(3) . . . . ?
N5 C9 S1 C6 -178.6(3) . . . . ?
N2 C6 S1 C9 1.4(2) . . . . ?
C5 C6 S1 C9 119.4(2) . . . . ?
C7 C6 S1 C9 -117.2(2) . . . . ?
C13 N5 C12 C15 -107.2(6) . . . . ?
C9 N5 C12 C15 102.3(6) . . . . ?
C12' N5 C12 C15 0.0(6) . . . . ?
C13 N5 C12' C15' 106.3(5) . . . . ?
C9 N5 C12' C15' -88.1(6) . . . . ?
C12 N5 C12' C15' 10.5(6) . . . . ?

_refine_diff_density_max         0.337
_refine_diff_density_min         -0.611
_refine_diff_density_rms         0.062

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1980370'
loop_
_audit_author_name
_audit_author_address
'S Athimoolam'
;University College of Engineering, Anna University Constituent College, Nagercoil 
India
;
_audit_update_record             
;
2020-01-28 deposited with the CCDC.	2021-12-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H19 N5 O4 S'
_chemical_formula_sum            'C16 H19 N5 O4 S'
_chemical_formula_weight         377.42

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   26.56(4)
_cell_length_b                   7.133(12)
_cell_length_c                   19.18(3)
_cell_angle_alpha                90
_cell_angle_beta                 95.72(2)
_cell_angle_gamma                90
_cell_volume                     3615(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2334
_cell_measurement_theta_min      2.73
_cell_measurement_theta_max      24.86

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    none
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_F_000             1584
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.17
_exptl_absorpt_coefficient_mu    0.212
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.3211
_exptl_special_details           
;
 The following wavelength and cell were deduced by SADABS from the
 direction cosines etc. They are given here for emergency use only:
 CELL 0.71058   26.578    7.153   19.181   89.943   95.567   89.932
;


_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16162
_diffrn_reflns_av_unetI/netI     0.0697
_diffrn_reflns_av_R_equivalents  0.0823
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.505
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.971
_reflns_number_total             3190
_reflns_number_gt                2098
_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       'SMART (Bruker, 2001)'
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2015)'
_computing_structure_refinement  SHELXL-2014
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  SHELXL-2014

_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)+(0.0657P)²+2.3816P] 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         3190
_refine_ls_number_parameters     239
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1023
_refine_ls_R_factor_gt           0.0581
_refine_ls_wR_factor_ref         0.1482
_refine_ls_wR_factor_gt          0.1298
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_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
C1 C 0.76063(9) 0.1561(4) 0.58894(16) 0.0403(7) Uani 1 1 d . . . . .
C2 C 0.73757(10) 0.0281(4) 0.54203(18) 0.0458(8) Uani 1 1 d . . . . .
H9 H 0.7575 -0.0483 0.5167 0.055 Uiso 1 1 calc R U . . .
C3 C 0.68555(10) 0.0112(4) 0.53198(17) 0.0434(8) Uani 1 1 d . . . . .
C4 C 0.65982(12) -0.1199(4) 0.4787(2) 0.0649(10) Uani 1 1 d . . . . .
H11 H 0.6443 -0.2202 0.5022 0.097 Uiso 1 1 calc R U . . .
H12 H 0.6843 -0.1705 0.4503 0.097 Uiso 1 1 calc R U . . .
H13 H 0.6344 -0.0529 0.4496 0.097 Uiso 1 1 calc R U . . .
C5 C 0.65786(9) 0.1244(4) 0.57342(16) 0.0429(8) Uani 1 1 d . . . . .
H10 H 0.6229 0.1109 0.5693 0.051 Uiso 1 1 calc R U . . .
C6 C 0.67914(9) 0.2541(4) 0.61972(16) 0.0382(7) Uani 1 1 d . . . . .
C7 C 0.73261(9) 0.2811(4) 0.62781(16) 0.0390(7) Uani 1 1 d . . . . .
C8 C 0.64566(9) 0.3671(4) 0.66406(17) 0.0462(8) Uani 1 1 d . . . . .
C9 C 0.67615(11) 0.4636(5) 0.72527(19) 0.0616(10) Uani 1 1 d . . . . .
H4 H 0.6553 0.5570 0.7453 0.074 Uiso 1 1 calc R U . . .
H5 H 0.6865 0.3721 0.7613 0.074 Uiso 1 1 calc R U . . .
C10 C 0.72214(11) 0.5560(5) 0.7010(2) 0.0638(10) Uani 1 1 d . . . . .
H6 H 0.7118 0.6521 0.6667 0.077 Uiso 1 1 calc R U . . .
H7 H 0.7416 0.6155 0.7404 0.077 Uiso 1 1 calc R U . . .
C11 C 0.61419(11) 0.0903(5) 0.72530(19) 0.0584(9) Uani 1 1 d . . . . .
C12 C 0.57024(12) -0.0223(5) 0.7435(2) 0.0765(12) Uani 1 1 d . . . . .
H14 H 0.5498 -0.0570 0.7014 0.115 Uiso 1 1 calc R U . . .
H15 H 0.5504 0.0508 0.7727 0.115 Uiso 1 1 calc R U . . .
H16 H 0.5822 -0.1333 0.7682 0.115 Uiso 1 1 calc R U . . .
C13 C 0.55367(9) 0.4579(4) 0.63356(17) 0.0438(8) Uani 1 1 d . . . . .
C14 C 0.46216(11) 0.4469(6) 0.6338(2) 0.0881(14) Uani 1 1 d . . . . .
H17 H 0.4648 0.4406 0.6840 0.132 Uiso 1 1 calc R U . . .
H18 H 0.4596 0.3224 0.6148 0.132 Uiso 1 1 calc R U . . .
H19 H 0.4326 0.5173 0.6172 0.132 Uiso 1 1 calc R U . . .
C15 C 0.50437(11) 0.6961(5) 0.56941(19) 0.0548(9) Uani 1 1 d . . . . .
C16 C 0.45367(11) 0.7832(5) 0.5494(2) 0.0736(12) Uani 1 1 d . . . . .
H2 H 0.4326 0.6963 0.5217 0.110 Uiso 1 1 calc R U . . .
H3 H 0.4578 0.8951 0.5228 0.110 Uiso 1 1 calc R U . . .
H20 H 0.4381 0.8142 0.5911 0.110 Uiso 1 1 calc R U . . .
N1 N 0.81500(9) 0.1595(3) 0.59565(16) 0.0497(7) Uani 1 1 d . . . . .
N2 N 0.75322(8) 0.4182(3) 0.67000(14) 0.0514(7) Uani 1 1 d . . . . .
H8 H 0.7856 0.4239 0.6787 0.062 Uiso 1 1 calc R U . . .
N3 N 0.60473(7) 0.2515(3) 0.68813(14) 0.0486(7) Uani 1 1 d . . . . .
N4 N 0.55509(8) 0.3119(4) 0.67179(14) 0.0474(7) Uani 1 1 d . . . . .
N5 N 0.50724(8) 0.5392(3) 0.61139(15) 0.0503(7) Uani 1 1 d . . . . .
O1 O 0.83779(8) 0.0579(3) 0.55839(17) 0.0857(9) Uani 1 1 d . . . . .
O2 O 0.83807(7) 0.2654(3) 0.63818(13) 0.0627(7) Uani 1 1 d . . . . .
O3 O 0.65810(8) 0.0413(4) 0.74097(14) 0.0779(8) Uani 1 1 d . . . . .
O4 O 0.54228(9) 0.7627(4) 0.54901(17) 0.0937(10) Uani 1 1 d . . . . .
S1 S 0.61056(3) 0.54589(11) 0.60867(5) 0.0562(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 1.381(4) . ?
C1 C7 1.419(4) . ?
C1 N1 1.437(4) . ?
C2 C3 1.381(4) . ?
C2 H9 0.9300 . ?
C3 C5 1.393(4) . ?
C3 C4 1.498(4) . ?
C4 H11 0.9600 . ?
C4 H12 0.9600 . ?
C4 H13 0.9600 . ?
C5 C6 1.365(4) . ?
C5 H10 0.9300 . ?
C6 C7 1.426(4) . ?
C6 C8 1.522(4) . ?
C7 N2 1.350(4) . ?
C8 N3 1.475(4) . ?
C8 C9 1.523(5) . ?
C8 S1 1.851(3) . ?
C9 C10 1.502(5) . ?
C9 H4 0.9700 . ?
C9 H5 0.9700 . ?
C10 N2 1.448(4) . ?
C10 H6 0.9700 . ?
C10 H7 0.9700 . ?
C11 O3 1.226(4) . ?
C11 N3 1.363(4) . ?
C11 C12 1.487(5) . ?
C12 H14 0.9600 . ?
C12 H15 0.9600 . ?
C12 H16 0.9600 . ?
C13 N4 1.272(4) . ?
C13 N5 1.390(4) . ?
C13 S1 1.746(3) . ?
C14 N5 1.468(4) . ?
C14 H17 0.9600 . ?
C14 H18 0.9600 . ?
C14 H19 0.9600 . ?
C15 O4 1.213(4) . ?
C15 N5 1.376(4) . ?
C15 C16 1.498(4) . ?
C16 H2 0.9600 . ?
C16 H3 0.9600 . ?
C16 H20 0.9600 . ?
N1 O1 1.220(3) . ?
N1 O2 1.229(3) . ?
N2 H8 0.8600 . ?
N3 N4 1.393(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 C7 122.4(3) . . ?
C2 C1 N1 116.5(3) . . ?
C7 C1 N1 121.1(3) . . ?
C1 C2 C3 121.4(3) . . ?
C1 C2 H9 119.3 . . ?
C3 C2 H9 119.3 . . ?
C2 C3 C5 116.6(3) . . ?
C2 C3 C4 122.1(3) . . ?
C5 C3 C4 121.3(3) . . ?
C3 C4 H11 109.5 . . ?
C3 C4 H12 109.5 . . ?
H11 C4 H12 109.5 . . ?
C3 C4 H13 109.5 . . ?
H11 C4 H13 109.5 . . ?
H12 C4 H13 109.5 . . ?
C6 C5 C3 123.8(3) . . ?
C6 C5 H10 118.1 . . ?
C3 C5 H10 118.1 . . ?
C5 C6 C7 120.4(3) . . ?
C5 C6 C8 119.7(2) . . ?
C7 C6 C8 119.9(3) . . ?
N2 C7 C1 124.6(2) . . ?
N2 C7 C6 120.2(3) . . ?
C1 C7 C6 115.2(3) . . ?
N3 C8 C6 111.6(3) . . ?
N3 C8 C9 111.3(3) . . ?
C6 C8 C9 112.0(2) . . ?
N3 C8 S1 102.72(19) . . ?
C6 C8 S1 109.5(2) . . ?
C9 C8 S1 109.3(2) . . ?
C10 C9 C8 110.2(3) . . ?
C10 C9 H4 109.6 . . ?
C8 C9 H4 109.6 . . ?
C10 C9 H5 109.6 . . ?
C8 C9 H5 109.6 . . ?
H4 C9 H5 108.1 . . ?
N2 C10 C9 110.1(3) . . ?
N2 C10 H6 109.6 . . ?
C9 C10 H6 109.6 . . ?
N2 C10 H7 109.6 . . ?
C9 C10 H7 109.6 . . ?
H6 C10 H7 108.2 . . ?
O3 C11 N3 119.4(3) . . ?
O3 C11 C12 122.6(3) . . ?
N3 C11 C12 118.1(3) . . ?
C11 C12 H14 109.5 . . ?
C11 C12 H15 109.5 . . ?
H14 C12 H15 109.5 . . ?
C11 C12 H16 109.5 . . ?
H14 C12 H16 109.5 . . ?
H15 C12 H16 109.5 . . ?
N4 C13 N5 119.5(3) . . ?
N4 C13 S1 118.4(2) . . ?
N5 C13 S1 122.1(3) . . ?
N5 C14 H17 109.5 . . ?
N5 C14 H18 109.5 . . ?
H17 C14 H18 109.5 . . ?
N5 C14 H19 109.5 . . ?
H17 C14 H19 109.5 . . ?
H18 C14 H19 109.5 . . ?
O4 C15 N5 120.5(3) . . ?
O4 C15 C16 120.6(3) . . ?
N5 C15 C16 118.9(3) . . ?
C15 C16 H2 109.5 . . ?
C15 C16 H3 109.5 . . ?
H2 C16 H3 109.5 . . ?
C15 C16 H20 109.5 . . ?
H2 C16 H20 109.5 . . ?
H3 C16 H20 109.5 . . ?
O1 N1 O2 120.7(3) . . ?
O1 N1 C1 119.4(3) . . ?
O2 N1 C1 120.0(3) . . ?
C7 N2 C10 121.6(2) . . ?
C7 N2 H8 119.2 . . ?
C10 N2 H8 119.2 . . ?
C11 N3 N4 120.0(2) . . ?
C11 N3 C8 122.2(2) . . ?
N4 N3 C8 117.9(2) . . ?
C13 N4 N3 110.9(2) . . ?
C15 N5 C13 120.9(2) . . ?
C15 N5 C14 122.5(2) . . ?
C13 N5 C14 116.6(3) . . ?
C13 S1 C8 89.75(16) . . ?

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
C7 C1 C2 C3 -2.0(5) . . . . ?
N1 C1 C2 C3 179.2(3) . . . . ?
C1 C2 C3 C5 -2.4(4) . . . . ?
C1 C2 C3 C4 176.8(3) . . . . ?
C2 C3 C5 C6 3.2(4) . . . . ?
C4 C3 C5 C6 -176.0(3) . . . . ?
C3 C5 C6 C7 0.3(4) . . . . ?
C3 C5 C6 C8 -178.3(3) . . . . ?
C2 C1 C7 N2 -174.5(3) . . . . ?
N1 C1 C7 N2 4.2(4) . . . . ?
C2 C1 C7 C6 5.3(4) . . . . ?
N1 C1 C7 C6 -175.9(2) . . . . ?
C5 C6 C7 N2 175.4(3) . . . . ?
C8 C6 C7 N2 -6.0(4) . . . . ?
C5 C6 C7 C1 -4.5(4) . . . . ?
C8 C6 C7 C1 174.2(3) . . . . ?
C5 C6 C8 N3 38.9(4) . . . . ?
C7 C6 C8 N3 -139.7(3) . . . . ?
C5 C6 C8 C9 164.5(3) . . . . ?
C7 C6 C8 C9 -14.1(4) . . . . ?
C5 C6 C8 S1 -74.1(3) . . . . ?
C7 C6 C8 S1 107.2(3) . . . . ?
N3 C8 C9 C10 171.3(2) . . . . ?
C6 C8 C9 C10 45.6(4) . . . . ?
S1 C8 C9 C10 -75.9(3) . . . . ?
C8 C9 C10 N2 -58.5(4) . . . . ?
C2 C1 N1 O1 3.2(4) . . . . ?
C7 C1 N1 O1 -175.6(3) . . . . ?
C2 C1 N1 O2 -177.5(3) . . . . ?
C7 C1 N1 O2 3.7(4) . . . . ?
C1 C7 N2 C10 171.9(3) . . . . ?
C6 C7 N2 C10 -8.0(4) . . . . ?
C9 C10 N2 C7 40.8(4) . . . . ?
O3 C11 N3 N4 -178.1(3) . . . . ?
C12 C11 N3 N4 3.6(5) . . . . ?
O3 C11 N3 C8 1.9(5) . . . . ?
C12 C11 N3 C8 -176.4(3) . . . . ?
C6 C8 N3 C11 56.1(4) . . . . ?
C9 C8 N3 C11 -69.9(4) . . . . ?
S1 C8 N3 C11 173.3(3) . . . . ?
C6 C8 N3 N4 -123.9(3) . . . . ?
C9 C8 N3 N4 110.1(3) . . . . ?
S1 C8 N3 N4 -6.7(3) . . . . ?
N5 C13 N4 N3 179.7(3) . . . . ?
S1 C13 N4 N3 1.5(4) . . . . ?
C11 N3 N4 C13 -176.1(3) . . . . ?
C8 N3 N4 C13 3.9(4) . . . . ?
O4 C15 N5 C13 2.5(5) . . . . ?
C16 C15 N5 C13 -177.4(3) . . . . ?
O4 C15 N5 C14 -176.1(4) . . . . ?
C16 C15 N5 C14 3.9(5) . . . . ?
N4 C13 N5 C15 -179.3(3) . . . . ?
S1 C13 N5 C15 -1.1(4) . . . . ?
N4 C13 N5 C14 -0.6(5) . . . . ?
S1 C13 N5 C14 177.6(3) . . . . ?
N4 C13 S1 C8 -4.7(3) . . . . ?
N5 C13 S1 C8 177.1(3) . . . . ?
N3 C8 S1 C13 5.8(2) . . . . ?
C6 C8 S1 C13 124.5(2) . . . . ?
C9 C8 S1 C13 -112.5(2) . . . . ?

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
C9 H5 O3 0.97 2.50 3.070(7) 117.8 .
N2 H8 O2 0.86 2.01 2.630(4) 128.1 .
N2 H8 O3 0.86 2.20 2.904(4) 138.5 4_656

_refine_diff_density_max         0.334
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.048

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_shelx_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1980335'
loop_
_audit_author_name
_audit_author_address
'S Athimoolam'
;University College of Engineering, Anna University
India
;
_audit_update_record             
;
2020-01-28 deposited with the CCDC.	2021-12-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H15 N5 O4 S'
_chemical_formula_sum            'C14 H15 N5 O4 S'
_chemical_formula_weight         349.37

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'

_space_group_crystal_system      tetragonal
_space_group_IT_number           88
_space_group_name_H-M_alt        'I 41/a'
_space_group_name_Hall           '-I 4ad'

_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'
'-y+1/4, x+3/4, z+3/4'
'y+1/4, -x+1/4, z+1/4'
'-x, -y+1/2, z'
'x+1/2, y+1/2, z+1/2'
'-y+3/4, x+5/4, z+5/4'
'y+3/4, -x+3/4, z+3/4'
'-x+1/2, -y+1, z+1/2'
'-x, -y, -z'
'y-1/4, -x-3/4, -z-3/4'
'-y-1/4, x-1/4, -z-1/4'
'x, y-1/2, -z'
'-x+1/2, -y+1/2, -z+1/2'
'y+1/4, -x-1/4, -z-1/4'
'-y+1/4, x+1/4, -z+1/4'
'x+1/2, y, -z+1/2'

_cell_length_a                   18.03(3)
_cell_length_b                   18.03(3)
_cell_length_c                   20.39(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     6627(26)
_cell_formula_units_Z            16
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      23.67

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    none
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_F_000             2912
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_exptl_absorpt_coefficient_mu    0.225
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6601
_exptl_special_details           
;
 The following wavelength and cell were deduced by SADABS from the
 direction cosines etc. They are given here for emergency use only:
 CELL 0.71073   18.046   18.045   20.429   89.997   90.003   90.010
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28469
_diffrn_reflns_av_unetI/netI     0.0249
_diffrn_reflns_av_R_equivalents  0.0503
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.259
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 0.972
_reflns_number_total             2922
_reflns_number_gt                2456
_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       'SMART (Bruker, 2001)'
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2015)'
_computing_structure_refinement  SHELXL-2014
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  SHELXL-2014

_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)+(0.0580P)²+6.7829P] 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         2922
_refine_ls_number_parameters     219
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0539
_refine_ls_R_factor_gt           0.0440
_refine_ls_wR_factor_ref         0.1224
_refine_ls_wR_factor_gt          0.1151
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_restrained_S_all      1.078
_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
C1 C 0.77585(16) 0.5647(2) 0.4535(3) 0.1246(19) Uani 1 1 d . . . . .
H1A H 0.7972 0.5701 0.4106 0.187 Uiso 1 1 calc R U . . .
H1B H 0.7803 0.5140 0.4675 0.187 Uiso 1 1 calc R U . . .
H1C H 0.8015 0.5963 0.4839 0.187 Uiso 1 1 calc R U . . .
C2 C 0.69614(13) 0.58576(13) 0.45124(16) 0.0624(7) Uani 1 1 d . . . . .
C3 C 0.57397(11) 0.54099(10) 0.42160(10) 0.0364(5) Uani 1 1 d . . . . .
C4 C 0.44359(11) 0.58722(10) 0.40051(10) 0.0351(4) Uani 1 1 d . . . . .
C5 C 0.43095(12) 0.61722(11) 0.33254(11) 0.0415(5) Uani 1 1 d . . . . .
C6 C 0.38934(14) 0.68341(12) 0.32584(11) 0.0490(6) Uani 1 1 d . . . . .
C7 C 0.38255(19) 0.71105(15) 0.26102(14) 0.0739(9) Uani 1 1 d . . . . .
C10 C 0.46224(16) 0.58334(15) 0.27881(12) 0.0617(7) Uani 1 1 d . . . . .
H5 H 0.4901 0.5405 0.2848 0.074 Uiso 1 1 calc R U . . .
C11 C 0.4534(2) 0.61113(19) 0.21636(15) 0.0909(11) Uani 1 1 d . . . . .
H11 H 0.4742 0.5869 0.1805 0.109 Uiso 1 1 calc R U . . .
C12 C 0.4139(2) 0.67446(19) 0.20804(15) 0.0955(12) Uani 1 1 d . . . . .
H6 H 0.4078 0.6937 0.1661 0.115 Uiso 1 1 calc R U . . .
C14 C 0.36967(14) 0.69097(12) 0.44512(11) 0.0479(6) Uani 1 1 d . . . . .
H14A H 0.3267 0.7040 0.4714 0.057 Uiso 1 1 calc R U . . .
H14B H 0.4127 0.7153 0.4639 0.057 Uiso 1 1 calc R U . . .
C15 C 0.38070(12) 0.60800(11) 0.44657(11) 0.0440(5) Uani 1 1 d . . . . .
H8 H 0.3354 0.5833 0.4331 0.053 Uiso 1 1 calc R U . . .
H9 H 0.3925 0.5921 0.4908 0.053 Uiso 1 1 calc R U . . .
C16 C 0.40901(12) 0.45528(11) 0.38102(11) 0.0430(5) Uani 1 1 d . . . . .
C17 C 0.43384(14) 0.37688(12) 0.37816(14) 0.0546(6) Uani 1 1 d . . . . .
H12 H 0.3921 0.3455 0.3689 0.082 Uiso 1 1 calc R U . . .
H13 H 0.4552 0.3631 0.4195 0.082 Uiso 1 1 calc R U . . .
H14 H 0.4703 0.3714 0.3442 0.082 Uiso 1 1 calc R U . . .
N1 N 0.3421(2) 0.77856(16) 0.24800(16) 0.1092(12) Uani 1 1 d . . . . .
N2 N 0.35907(13) 0.71621(11) 0.37906(10) 0.0596(6) Uani 1 1 d . . . . .
H7 H 0.3317 0.7547 0.3730 0.072 Uiso 1 1 calc R U . . .
N3 N 0.45959(9) 0.50674(9) 0.40019(9) 0.0378(4) Uani 1 1 d . . . . .
N4 N 0.53375(9) 0.48537(9) 0.40646(9) 0.0368(4) Uani 1 1 d . . . . .
N5 N 0.64938(9) 0.53236(9) 0.42801(10) 0.0467(5) Uani 1 1 d . . . . .
H4 H 0.6683 0.4905 0.4166 0.056 Uiso 1 1 calc R U . . .
O3 O 0.34550(9) 0.47432(9) 0.36758(10) 0.0629(5) Uani 1 1 d . . . . .
O4 O 0.67336(10) 0.64550(9) 0.46913(12) 0.0788(7) Uani 1 1 d . . . . .
S1 S 0.53119(3) 0.62679(3) 0.43330(3) 0.0460(2) Uani 1 1 d . . . . .
O1 O 0.3168(2) 0.81527(15) 0.29331(15) 0.1303(12) Uani 1 1 d . . . . .
O2 O 0.3339(3) 0.79815(16) 0.19184(13) 0.1747(19) 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 1.487(4) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 O4 1.209(3) . ?
C2 N5 1.365(3) . ?
C3 N4 1.275(3) . ?
C3 N5 1.375(3) . ?
C3 S1 1.745(2) . ?
C4 N3 1.479(2) . ?
C4 C5 1.505(4) . ?
C4 C15 1.519(3) . ?
C4 S1 1.857(3) . ?
C5 C10 1.376(4) . ?
C5 C6 1.416(3) . ?
C6 N2 1.351(4) . ?
C6 C7 1.418(4) . ?
C7 C12 1.386(5) . ?
C7 N1 1.444(4) . ?
C10 C11 1.378(5) . ?
C10 H5 0.9300 . ?
C11 C12 1.356(5) . ?
C11 H11 0.9300 . ?
C12 H6 0.9300 . ?
C14 N2 1.435(4) . ?
C14 C15 1.509(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H8 0.9700 . ?
C15 H9 0.9700 . ?
C16 O3 1.226(3) . ?
C16 N3 1.358(3) . ?
C16 C17 1.484(3) . ?
C17 H12 0.9600 . ?
C17 H13 0.9600 . ?
C17 H14 0.9600 . ?
N1 O2 1.207(4) . ?
N1 O1 1.225(4) . ?
N2 H7 0.8600 . ?
N3 N4 1.397(3) . ?
N5 H4 0.8600 . ?

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 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O4 C2 N5 121.6(2) . . ?
O4 C2 C1 123.2(2) . . ?
N5 C2 C1 115.3(2) . . ?
N4 C3 N5 119.76(18) . . ?
N4 C3 S1 118.60(17) . . ?
N5 C3 S1 121.64(14) . . ?
N3 C4 C5 112.20(17) . . ?
N3 C4 C15 112.96(16) . . ?
C5 C4 C15 111.57(19) . . ?
N3 C4 S1 102.27(13) . . ?
C5 C4 S1 108.80(14) . . ?
C15 C4 S1 108.50(18) . . ?
C10 C5 C6 121.0(2) . . ?
C10 C5 C4 120.8(2) . . ?
C6 C5 C4 118.15(19) . . ?
N2 C6 C5 120.3(2) . . ?
N2 C6 C7 124.1(2) . . ?
C5 C6 C7 115.6(2) . . ?
C12 C7 C6 121.6(3) . . ?
C12 C7 N1 117.6(3) . . ?
C6 C7 N1 120.8(3) . . ?
C5 C10 C11 121.8(3) . . ?
C5 C10 H5 119.1 . . ?
C11 C10 H5 119.1 . . ?
C12 C11 C10 118.8(3) . . ?
C12 C11 H11 120.6 . . ?
C10 C11 H11 120.6 . . ?
C11 C12 C7 121.1(3) . . ?
C11 C12 H6 119.4 . . ?
C7 C12 H6 119.4 . . ?
N2 C14 C15 110.50(19) . . ?
N2 C14 H14A 109.5 . . ?
C15 C14 H14A 109.5 . . ?
N2 C14 H14B 109.5 . . ?
C15 C14 H14B 109.5 . . ?
H14A C14 H14B 108.1 . . ?
C14 C15 C4 109.30(17) . . ?
C14 C15 H8 109.8 . . ?
C4 C15 H8 109.8 . . ?
C14 C15 H9 109.8 . . ?
C4 C15 H9 109.8 . . ?
H8 C15 H9 108.3 . . ?
O3 C16 N3 120.0(2) . . ?
O3 C16 C17 122.64(19) . . ?
N3 C16 C17 117.35(19) . . ?
C16 C17 H12 109.5 . . ?
C16 C17 H13 109.5 . . ?
H12 C17 H13 109.5 . . ?
C16 C17 H14 109.5 . . ?
H12 C17 H14 109.5 . . ?
H13 C17 H14 109.5 . . ?
O2 N1 O1 120.8(3) . . ?
O2 N1 C7 118.9(3) . . ?
O1 N1 C7 120.4(3) . . ?
C6 N2 C14 124.2(2) . . ?
C6 N2 H7 117.9 . . ?
C14 N2 H7 117.9 . . ?
C16 N3 N4 118.71(17) . . ?
C16 N3 C4 122.70(17) . . ?
N4 N3 C4 117.17(15) . . ?
C3 N4 N3 110.45(17) . . ?
C2 N5 C3 124.34(19) . . ?
C2 N5 H4 117.8 . . ?
C3 N5 H4 117.8 . . ?
C3 S1 C4 89.20(12) . . ?

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
N3 C4 C5 C10 -26.4(3) . . . . ?
C15 C4 C5 C10 -154.3(2) . . . . ?
S1 C4 C5 C10 86.0(2) . . . . ?
N3 C4 C5 C6 156.93(19) . . . . ?
C15 C4 C5 C6 29.0(3) . . . . ?
S1 C4 C5 C6 -90.6(2) . . . . ?
C10 C5 C6 N2 -179.8(2) . . . . ?
C4 C5 C6 N2 -3.2(3) . . . . ?
C10 C5 C6 C7 0.2(4) . . . . ?
C4 C5 C6 C7 176.8(2) . . . . ?
N2 C6 C7 C12 -179.1(3) . . . . ?
C5 C6 C7 C12 0.9(5) . . . . ?
N2 C6 C7 N1 0.6(5) . . . . ?
C5 C6 C7 N1 -179.4(3) . . . . ?
C6 C5 C10 C11 -1.3(4) . . . . ?
C4 C5 C10 C11 -177.9(3) . . . . ?
C5 C10 C11 C12 1.3(5) . . . . ?
C10 C11 C12 C7 -0.1(6) . . . . ?
C6 C7 C12 C11 -1.0(6) . . . . ?
N1 C7 C12 C11 179.3(4) . . . . ?
N2 C14 C15 C4 54.1(3) . . . . ?
N3 C4 C15 C14 178.48(18) . . . . ?
C5 C4 C15 C14 -54.0(2) . . . . ?
S1 C4 C15 C14 65.8(2) . . . . ?
C12 C7 N1 O2 3.8(6) . . . . ?
C6 C7 N1 O2 -175.9(4) . . . . ?
C12 C7 N1 O1 -176.0(4) . . . . ?
C6 C7 N1 O1 4.3(6) . . . . ?
C5 C6 N2 C14 4.0(4) . . . . ?
C7 C6 N2 C14 -176.0(3) . . . . ?
C15 C14 N2 C6 -30.5(3) . . . . ?
O3 C16 N3 N4 -171.3(2) . . . . ?
C17 C16 N3 N4 9.5(3) . . . . ?
O3 C16 N3 C4 -5.3(3) . . . . ?
C17 C16 N3 C4 175.5(2) . . . . ?
C5 C4 N3 C16 -65.3(3) . . . . ?
C15 C4 N3 C16 61.9(3) . . . . ?
S1 C4 N3 C16 178.27(17) . . . . ?
C5 C4 N3 N4 100.9(2) . . . . ?
C15 C4 N3 N4 -131.9(2) . . . . ?
S1 C4 N3 N4 -15.5(2) . . . . ?
N5 C3 N4 N3 -177.86(19) . . . . ?
S1 C3 N4 N3 1.9(2) . . . . ?
C16 N3 N4 C3 176.79(19) . . . . ?
C4 N3 N4 C3 10.0(3) . . . . ?
O4 C2 N5 C3 1.2(5) . . . . ?
C1 C2 N5 C3 -179.5(3) . . . . ?
N4 C3 N5 C2 -172.1(2) . . . . ?
S1 C3 N5 C2 8.2(3) . . . . ?
N4 C3 S1 C4 -9.49(18) . . . . ?
N5 C3 S1 C4 170.22(19) . . . . ?
N3 C4 S1 C3 12.66(14) . . . . ?
C5 C4 S1 C3 -106.19(16) . . . . ?
C15 C4 S1 C3 132.24(15) . . . . ?

_refine_diff_density_max         0.409
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.046

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_shelx_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 1980306'
loop_
_audit_author_name
_audit_author_address
'S Athimoolam'
;University College of Engineering, Anna University Constituent College, Nagercoil 
India
;
_audit_update_record             
;
2020-01-28 deposited with the CCDC.	2021-12-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H19 N5 O4 S'
_chemical_formula_sum            'C20 H19 N5 O4 S'
_chemical_formula_weight         425.46

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'

_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                   8.796(2)
_cell_length_b                   11.281(3)
_cell_length_c                   11.333(3)
_cell_angle_alpha                65.16(5)
_cell_angle_beta                 87.05(7)
_cell_angle_gamma                84.17(7)
_cell_volume                     1015.1(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2987
_cell_measurement_theta_min      2.14
_cell_measurement_theta_max      24.62

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    none
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_F_000             444
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.14
_exptl_absorpt_coefficient_mu    0.197
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6738
_exptl_special_details           
;
 The following wavelength and cell were deduced by SADABS from the
 direction cosines etc. They are given here for emergency use only:
 CELL 0.71069    8.790   11.284   11.319   65.161   87.112   84.115
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19566
_diffrn_reflns_av_unetI/netI     0.0635
_diffrn_reflns_av_R_equivalents  0.0811
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.147
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.975
_reflns_number_total             3591
_reflns_number_gt                2519
_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       'SMART (Bruker, 2001)'
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2015)'
_computing_structure_refinement  SHELXL-2014
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  SHELXL-2014

_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)+(0.0898P)²+0.2080P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3591
_refine_ls_number_parameters     277
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0996
_refine_ls_R_factor_gt           0.0643
_refine_ls_wR_factor_ref         0.1712
_refine_ls_wR_factor_gt          0.1540
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_restrained_S_all      1.110
_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
S1 S 0.90300(10) 0.57788(8) 0.77330(8) 0.0340(3) Uani 1 1 d . . . . .
O2 O 0.7085(4) 0.2496(3) 1.2701(2) 0.0665(8) Uani 1 1 d . . . . .
O4 O 0.9113(3) 0.8261(2) 0.7091(2) 0.0525(7) Uani 1 1 d . . . . .
O3 O 0.7983(3) 0.2400(2) 0.6789(2) 0.0482(7) Uani 1 1 d . . . . .
N5 N 0.8127(3) 0.7900(2) 0.5464(2) 0.0331(7) Uani 1 1 d . . . . .
N3 N 0.8274(3) 0.4488(2) 0.6440(2) 0.0324(6) Uani 1 1 d . . . . .
N4 N 0.8017(3) 0.5812(2) 0.5579(2) 0.0331(6) Uani 1 1 d . . . . .
N2 N 0.8638(4) 0.3019(3) 1.0525(3) 0.0423(8) Uani 1 1 d . . . . .
O1 O 0.4687(4) 0.2269(4) 1.2770(3) 0.0925(12) Uani 1 1 d . . . . .
N1 N 0.5877(4) 0.2580(3) 1.2159(3) 0.0511(8) Uani 1 1 d . . . . .
C3 C 0.5856(4) 0.3082(3) 1.0748(3) 0.0357(8) Uani 1 1 d . . . . .
C4 C 0.7226(4) 0.3293(3) 1.0017(3) 0.0292(7) Uani 1 1 d . . . . .
C5 C 0.7057(3) 0.3851(3) 0.8636(3) 0.0283(7) Uani 1 1 d . . . . .
C6 C 0.8501(4) 0.4192(3) 0.7821(3) 0.0294(7) Uani 1 1 d . . . . .
C7 C 0.8340(3) 0.6536(3) 0.6140(3) 0.0302(7) Uani 1 1 d . . . . .
C8 C 0.7533(4) 0.8435(3) 0.4154(3) 0.0329(8) Uani 1 1 d . . . . .
C9 C 0.6028(4) 0.8354(4) 0.3954(4) 0.0505(10) Uani 1 1 d . . . . .
H12 H 0.5382 0.7951 0.4656 0.061 Uiso 1 1 calc R U . . .
C10 C 0.5484(5) 0.8875(5) 0.2701(5) 0.0676(12) Uani 1 1 d . . . . .
H11 H 0.4472 0.8805 0.2555 0.081 Uiso 1 1 calc R U . . .
C11 C 0.6438(5) 0.9501(4) 0.1662(4) 0.0631(12) Uani 1 1 d . . . . .
H2 H 0.6061 0.9866 0.0820 0.076 Uiso 1 1 calc R U . . .
C12 C 0.5628(4) 0.4131(3) 0.8098(3) 0.0412(9) Uani 1 1 d . . . . .
H5 H 0.5546 0.4492 0.7198 0.049 Uiso 1 1 calc R U . . .
C13 C 0.4298(4) 0.3893(4) 0.8854(4) 0.0510(10) Uani 1 1 d . . . . .
H3 H 0.3343 0.4090 0.8467 0.061 Uiso 1 1 calc R U . . .
C14 C 0.4427(4) 0.3365(4) 1.0172(4) 0.0465(9) Uani 1 1 d . . . . .
H4 H 0.3552 0.3193 1.0692 0.056 Uiso 1 1 calc R U . . .
C15 C 0.8419(4) 0.8712(3) 0.6073(3) 0.0390(8) Uani 1 1 d . . . . .
C16 C 0.7809(5) 1.0109(3) 0.5417(4) 0.0530(10) Uani 1 1 d . . . . .
H6 H 0.7948 1.0544 0.5967 0.080 Uiso 1 1 calc R U . . .
H8 H 0.6740 1.0157 0.5252 0.080 Uiso 1 1 calc R U . . .
H7 H 0.8345 1.0528 0.4609 0.080 Uiso 1 1 calc R U . . .
C17 C 0.7926(5) 0.9587(4) 0.1863(4) 0.0540(10) Uani 1 1 d . . . . .
H10 H 0.8563 1.0012 0.1161 0.065 Uiso 1 1 calc R U . . .
C18 C 0.8492(4) 0.9037(3) 0.3120(3) 0.0426(9) Uani 1 1 d . . . . .
H9 H 0.9514 0.9076 0.3262 0.051 Uiso 1 1 calc R U . . .
C19 C 0.7935(4) 0.3565(3) 0.6024(3) 0.0342(8) Uani 1 1 d . . . . .
C20 C 0.7519(5) 0.4046(4) 0.4631(3) 0.0538(10) Uani 1 1 d . . . . .
H13 H 0.7545 0.3315 0.4402 0.081 Uiso 1 1 calc R U . . .
H15 H 0.8234 0.4643 0.4096 0.081 Uiso 1 1 calc R U . . .
H14 H 0.6509 0.4488 0.4497 0.081 Uiso 1 1 calc R U . . .
C21 C 0.9787(4) 0.3125(3) 0.8478(3) 0.0368(8) Uani 1 1 d . . . . .
H16 H 0.9506 0.2284 0.8557 0.044 Uiso 1 1 calc R U . . .
H17 H 1.0714 0.3323 0.7956 0.044 Uiso 1 1 calc R U . . .
C22 C 1.0062(4) 0.3060(3) 0.9816(3) 0.0416(9) Uani 1 1 d . . . . .
H18 H 1.0734 0.2284 1.0300 0.050 Uiso 1 1 calc R U . . .
H19 H 1.0562 0.3822 0.9726 0.050 Uiso 1 1 calc R U . . .
H2N H 0.868(4) 0.271(3) 1.128(4) 0.041(11) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C7 1.752(3) . ?
S1 C6 1.856(3) . ?
O2 N1 1.230(4) . ?
O4 C15 1.216(4) . ?
O3 C19 1.231(4) . ?
N5 C7 1.398(4) . ?
N5 C15 1.406(4) . ?
N5 C8 1.452(4) . ?
N3 C19 1.374(4) . ?
N3 N4 1.401(4) . ?
N3 C6 1.476(4) . ?
N4 C7 1.286(4) . ?
N2 C4 1.347(4) . ?
N2 C22 1.447(5) . ?
N2 H2N 0.77(4) . ?
O1 N1 1.223(4) . ?
N1 C3 1.455(4) . ?
C3 C14 1.391(5) . ?
C3 C4 1.410(5) . ?
C4 C5 1.429(4) . ?
C5 C12 1.373(4) . ?
C5 C6 1.515(4) . ?
C6 C21 1.530(5) . ?
C8 C9 1.373(5) . ?
C8 C18 1.375(5) . ?
C9 C10 1.379(5) . ?
C9 H12 0.9300 . ?
C10 C11 1.382(6) . ?
C10 H11 0.9300 . ?
C11 C17 1.359(6) . ?
C11 H2 0.9300 . ?
C12 C13 1.394(5) . ?
C12 H5 0.9300 . ?
C13 C14 1.362(5) . ?
C13 H3 0.9300 . ?
C14 H4 0.9300 . ?
C15 C16 1.487(5) . ?
C16 H6 0.9600 . ?
C16 H8 0.9600 . ?
C16 H7 0.9600 . ?
C17 C18 1.389(5) . ?
C17 H10 0.9300 . ?
C18 H9 0.9300 . ?
C19 C20 1.490(5) . ?
C20 H13 0.9600 . ?
C20 H15 0.9600 . ?
C20 H14 0.9600 . ?
C21 C22 1.519(5) . ?
C21 H16 0.9700 . ?
C21 H17 0.9700 . ?
C22 H18 0.9700 . ?
C22 H19 0.9700 . ?

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
C7 S1 C6 88.65(15) . . ?
C7 N5 C15 120.2(3) . . ?
C7 N5 C8 117.9(3) . . ?
C15 N5 C8 121.8(3) . . ?
C19 N3 N4 117.8(3) . . ?
C19 N3 C6 123.1(2) . . ?
N4 N3 C6 117.1(2) . . ?
C7 N4 N3 109.5(3) . . ?
C4 N2 C22 126.0(3) . . ?
C4 N2 H2N 116(3) . . ?
C22 N2 H2N 117(3) . . ?
O1 N1 O2 121.9(3) . . ?
O1 N1 C3 118.9(4) . . ?
O2 N1 C3 119.2(3) . . ?
C14 C3 C4 122.4(3) . . ?
C14 C3 N1 116.7(3) . . ?
C4 C3 N1 120.8(3) . . ?
N2 C4 C3 124.8(3) . . ?
N2 C4 C5 119.4(3) . . ?
C3 C4 C5 115.7(3) . . ?
C12 C5 C4 120.4(3) . . ?
C12 C5 C6 122.6(3) . . ?
C4 C5 C6 116.9(3) . . ?
N3 C6 C5 113.2(3) . . ?
N3 C6 C21 114.4(3) . . ?
C5 C6 C21 109.1(3) . . ?
N3 C6 S1 102.35(19) . . ?
C5 C6 S1 108.3(2) . . ?
C21 C6 S1 109.2(2) . . ?
N4 C7 N5 119.2(3) . . ?
N4 C7 S1 118.8(2) . . ?
N5 C7 S1 122.0(2) . . ?
C9 C8 C18 120.6(3) . . ?
C9 C8 N5 120.2(3) . . ?
C18 C8 N5 119.1(3) . . ?
C8 C9 C10 119.3(4) . . ?
C8 C9 H12 120.3 . . ?
C10 C9 H12 120.3 . . ?
C9 C10 C11 120.1(4) . . ?
C9 C10 H11 119.9 . . ?
C11 C10 H11 119.9 . . ?
C17 C11 C10 120.4(4) . . ?
C17 C11 H2 119.8 . . ?
C10 C11 H2 119.8 . . ?
C5 C12 C13 122.3(3) . . ?
C5 C12 H5 118.8 . . ?
C13 C12 H5 118.8 . . ?
C14 C13 C12 118.5(3) . . ?
C14 C13 H3 120.7 . . ?
C12 C13 H3 120.7 . . ?
C13 C14 C3 120.6(3) . . ?
C13 C14 H4 119.7 . . ?
C3 C14 H4 119.7 . . ?
O4 C15 N5 120.3(3) . . ?
O4 C15 C16 123.4(3) . . ?
N5 C15 C16 116.3(3) . . ?
C15 C16 H6 109.5 . . ?
C15 C16 H8 109.5 . . ?
H6 C16 H8 109.5 . . ?
C15 C16 H7 109.5 . . ?
H6 C16 H7 109.5 . . ?
H8 C16 H7 109.5 . . ?
C11 C17 C18 119.8(4) . . ?
C11 C17 H10 120.1 . . ?
C18 C17 H10 120.1 . . ?
C8 C18 C17 119.6(4) . . ?
C8 C18 H9 120.2 . . ?
C17 C18 H9 120.2 . . ?
O3 C19 N3 120.1(3) . . ?
O3 C19 C20 122.9(3) . . ?
N3 C19 C20 117.0(3) . . ?
C19 C20 H13 109.5 . . ?
C19 C20 H15 109.5 . . ?
H13 C20 H15 109.5 . . ?
C19 C20 H14 109.5 . . ?
H13 C20 H14 109.5 . . ?
H15 C20 H14 109.5 . . ?
C22 C21 C6 109.1(3) . . ?
C22 C21 H16 109.9 . . ?
C6 C21 H16 109.9 . . ?
C22 C21 H17 109.9 . . ?
C6 C21 H17 109.9 . . ?
H16 C21 H17 108.3 . . ?
N2 C22 C21 110.9(3) . . ?
N2 C22 H18 109.5 . . ?
C21 C22 H18 109.5 . . ?
N2 C22 H19 109.5 . . ?
C21 C22 H19 109.5 . . ?
H18 C22 H19 108.0 . . ?

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
C19 N3 N4 C7 177.6(3) . . . . ?
C6 N3 N4 C7 13.1(4) . . . . ?
O1 N1 C3 C14 9.7(5) . . . . ?
O2 N1 C3 C14 -169.5(3) . . . . ?
O1 N1 C3 C4 -171.7(3) . . . . ?
O2 N1 C3 C4 9.1(5) . . . . ?
C22 N2 C4 C3 171.3(3) . . . . ?
C22 N2 C4 C5 -9.4(5) . . . . ?
C14 C3 C4 N2 -179.0(3) . . . . ?
N1 C3 C4 N2 2.5(5) . . . . ?
C14 C3 C4 C5 1.6(4) . . . . ?
N1 C3 C4 C5 -176.9(3) . . . . ?
N2 C4 C5 C12 179.6(3) . . . . ?
C3 C4 C5 C12 -0.9(4) . . . . ?
N2 C4 C5 C6 -4.3(4) . . . . ?
C3 C4 C5 C6 175.2(3) . . . . ?
C19 N3 C6 C5 -67.0(4) . . . . ?
N4 N3 C6 C5 96.7(3) . . . . ?
C19 N3 C6 C21 58.8(4) . . . . ?
N4 N3 C6 C21 -137.6(3) . . . . ?
C19 N3 C6 S1 176.7(2) . . . . ?
N4 N3 C6 S1 -19.6(3) . . . . ?
C12 C5 C6 N3 -16.5(4) . . . . ?
C4 C5 C6 N3 167.5(2) . . . . ?
C12 C5 C6 C21 -145.1(3) . . . . ?
C4 C5 C6 C21 38.9(3) . . . . ?
C12 C5 C6 S1 96.2(3) . . . . ?
C4 C5 C6 S1 -79.8(3) . . . . ?
C7 S1 C6 N3 15.6(2) . . . . ?
C7 S1 C6 C5 -104.2(2) . . . . ?
C7 S1 C6 C21 137.1(2) . . . . ?
N3 N4 C7 N5 -178.3(2) . . . . ?
N3 N4 C7 S1 1.5(4) . . . . ?
C15 N5 C7 N4 177.7(3) . . . . ?
C8 N5 C7 N4 0.5(4) . . . . ?
C15 N5 C7 S1 -2.1(4) . . . . ?
C8 N5 C7 S1 -179.3(2) . . . . ?
C6 S1 C7 N4 -11.1(3) . . . . ?
C6 S1 C7 N5 168.6(3) . . . . ?
C7 N5 C8 C9 72.5(4) . . . . ?
C15 N5 C8 C9 -104.6(4) . . . . ?
C7 N5 C8 C18 -108.3(3) . . . . ?
C15 N5 C8 C18 74.5(4) . . . . ?
C18 C8 C9 C10 0.5(5) . . . . ?
N5 C8 C9 C10 179.6(3) . . . . ?
C8 C9 C10 C11 -1.6(6) . . . . ?
C9 C10 C11 C17 1.3(7) . . . . ?
C4 C5 C12 C13 0.2(5) . . . . ?
C6 C5 C12 C13 -175.7(3) . . . . ?
C5 C12 C13 C14 0.1(5) . . . . ?
C12 C13 C14 C3 0.6(5) . . . . ?
C4 C3 C14 C13 -1.5(5) . . . . ?
N1 C3 C14 C13 177.1(3) . . . . ?
C7 N5 C15 O4 13.3(5) . . . . ?
C8 N5 C15 O4 -169.6(3) . . . . ?
C7 N5 C15 C16 -165.4(3) . . . . ?
C8 N5 C15 C16 11.7(5) . . . . ?
C10 C11 C17 C18 0.3(6) . . . . ?
C9 C8 C18 C17 1.0(5) . . . . ?
N5 C8 C18 C17 -178.1(3) . . . . ?
C11 C17 C18 C8 -1.4(5) . . . . ?
N4 N3 C19 O3 -172.1(3) . . . . ?
C6 N3 C19 O3 -8.5(5) . . . . ?
N4 N3 C19 C20 7.9(4) . . . . ?
C6 N3 C19 C20 171.5(3) . . . . ?
N3 C6 C21 C22 171.4(3) . . . . ?
C5 C6 C21 C22 -60.6(3) . . . . ?
S1 C6 C21 C22 57.5(3) . . . . ?
C4 N2 C22 C21 -14.1(5) . . . . ?
C6 C21 C22 N2 48.4(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
C16 H6 O3 0.96 2.63 3.549(4) 161.1 1_565
C16 H7 O2 0.96 2.56 3.166(5) 121.3 1_564
C18 H9 O3 0.93 2.64 3.336(5) 132.5 2_766
C20 H13 O2 0.96 2.53 3.379(5) 147.9 1_554
C21 H16 O3 0.97 2.42 2.956(4) 114.5 .
N2 H2N O2 0.77(4) 2.03(4) 2.625(4) 133(3) .
N2 H2N O4 0.77(4) 2.58(4) 3.161(5) 134(3) 2_767

_refine_diff_density_max         0.796
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.079

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_shelx_CCDC4
_database_code_depnum_ccdc_archive 'CCDC 1980270'
loop_
_audit_author_name
_audit_author_address
'S Athimoolam'
;University College of Engineering, Anna University Constituent College, Nagercoil
India
;
_audit_update_record             
;
2020-01-28 deposited with the CCDC.	2021-12-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H21 N5 O4 S'
_chemical_formula_sum            'C21 H21 N5 O4 S'
_chemical_formula_weight         439.49

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'

_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                   9.7258(17)
_cell_length_b                   11.0684(19)
_cell_length_c                   20.736(3)
_cell_angle_alpha                90
_cell_angle_beta                 99.75(3)
_cell_angle_gamma                90
_cell_volume                     2200.0(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2415
_cell_measurement_theta_min      2.16
_cell_measurement_theta_max      24.82

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    none
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_F_000             920
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.13
_exptl_absorpt_coefficient_mu    0.184
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6466
_exptl_special_details           
;
 The following wavelength and cell were deduced by SADABS from the
 direction cosines etc. They are given here for emergency use only:
 CELL 0.71068    9.628   10.956   20.522   90.113   99.684   89.940
;


_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16122
_diffrn_reflns_av_unetI/netI     0.0322
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.092
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 0.974
_reflns_number_total             3880
_reflns_number_gt                3174
_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       'SMART (Bruker, 2001)'
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2015)'
_computing_structure_refinement  SHELXL-2014
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  SHELXL-2014

_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)+(0.0450P)²+1.0697P] 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         3880
_refine_ls_number_parameters     283
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0559
_refine_ls_R_factor_gt           0.0436
_refine_ls_wR_factor_ref         0.1136
_refine_ls_wR_factor_gt          0.1073
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_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 0.4026(2) 0.5824(2) 0.77880(10) 0.0474(5) Uani 1 1 d . . . . .
C2 C 0.2670(3) 0.5544(2) 0.78826(10) 0.0542(6) Uani 1 1 d . . . . .
H14 H 0.2382 0.5777 0.8270 0.065 Uiso 1 1 calc R U . . .
C3 C 0.1741(2) 0.4926(2) 0.74110(11) 0.0541(6) Uani 1 1 d . . . . .
C4 C 0.0282(3) 0.4583(4) 0.75206(14) 0.0871(10) Uani 1 1 d . . . . .
H15 H -0.0307 0.4451 0.7106 0.131 Uiso 1 1 calc R U . . .
H16 H -0.0096 0.5225 0.7748 0.131 Uiso 1 1 calc R U . . .
H17 H 0.0328 0.3857 0.7777 0.131 Uiso 1 1 calc R U . . .
C5 C 0.2229(2) 0.4607(2) 0.68265(10) 0.0464(5) Uani 1 1 d . . . . .
H18 H 0.1628 0.4196 0.6504 0.056 Uiso 1 1 calc R U . . .
C6 C 0.3565(2) 0.48810(18) 0.67130(9) 0.0372(5) Uani 1 1 d . . . . .
C7 C 0.4543(2) 0.54851(18) 0.72049(9) 0.0415(5) Uani 1 1 d . . . . .
C8 C 0.4009(2) 0.45023(18) 0.60637(9) 0.0376(5) Uani 1 1 d . . . . .
C9 C 0.5360(2) 0.5146(2) 0.59484(10) 0.0496(6) Uani 1 1 d . . . . .
H3 H 0.5726 0.4749 0.5596 0.059 Uiso 1 1 calc R U . . .
H19 H 0.5152 0.5978 0.5821 0.059 Uiso 1 1 calc R U . . .
C10 C 0.6446(2) 0.5115(2) 0.65687(11) 0.0548(6) Uani 1 1 d . . . . .
H20 H 0.6694 0.4284 0.6683 0.066 Uiso 1 1 calc R U . . .
H21 H 0.7282 0.5534 0.6495 0.066 Uiso 1 1 calc R U . . .
C11 C 0.2333(2) 0.58270(19) 0.53081(10) 0.0425(5) Uani 1 1 d . . . . .
C12 C 0.1301(3) 0.5945(2) 0.46737(11) 0.0549(6) Uani 1 1 d . . . . .
H11 H 0.1152 0.5166 0.4469 0.082 Uiso 1 1 calc R U . . .
H12 H 0.1666 0.6490 0.4385 0.082 Uiso 1 1 calc R U . . .
H13 H 0.0431 0.6252 0.4766 0.082 Uiso 1 1 calc R U . . .
C13 C 0.3103(2) 0.27152(18) 0.53042(9) 0.0357(4) Uani 1 1 d . . . . .
C14 C 0.3302(2) 0.0499(2) 0.52302(11) 0.0487(5) Uani 1 1 d . . . . .
C15 C 0.2818(3) -0.0626(2) 0.48381(14) 0.0689(7) Uani 1 1 d . . . . .
H4 H 0.3221 -0.0641 0.4447 0.103 Uiso 1 1 calc R U . . .
H5 H 0.1819 -0.0617 0.4724 0.103 Uiso 1 1 calc R U . . .
H6 H 0.3106 -0.1330 0.5096 0.103 Uiso 1 1 calc R U . . .
C16 C 0.1986(2) 0.17165(19) 0.42991(10) 0.0440(5) Uani 1 1 d . . . . .
C17 C 0.0548(3) 0.1877(2) 0.42262(13) 0.0642(7) Uani 1 1 d . . . . .
H10 H 0.0103 0.1864 0.4589 0.077 Uiso 1 1 calc R U . . .
C18 C -0.0224(3) 0.2060(3) 0.35945(17) 0.0867(10) Uani 1 1 d . . . . .
H9 H -0.1184 0.2177 0.3538 0.104 Uiso 1 1 calc R U . . .
C19 C 0.0454(4) 0.2065(3) 0.30567(15) 0.0910(11) Uani 1 1 d . . . . .
H2 H -0.0054 0.2200 0.2641 0.109 Uiso 1 1 calc R U . . .
C20 C 0.1880(4) 0.1872(3) 0.31318(13) 0.0781(9) Uani 1 1 d . . . . .
H8 H 0.2317 0.1850 0.2766 0.094 Uiso 1 1 calc R U . . .
C21 C 0.2665(3) 0.1710(2) 0.37564(11) 0.0594(6) Uani 1 1 d . . . . .
H7 H 0.3625 0.1600 0.3810 0.071 Uiso 1 1 calc R U . . .
N1 N 0.4913(3) 0.6435(2) 0.83316(10) 0.0649(6) Uani 1 1 d . . . . .
N2 N 0.58885(19) 0.56940(19) 0.71074(9) 0.0545(5) Uani 1 1 d . . . . .
H22 H 0.6413 0.6174 0.7367 0.065 Uiso 1 1 calc R U . . .
N3 N 0.28713(17) 0.46882(14) 0.54843(7) 0.0367(4) Uani 1 1 d . . . . .
N4 N 0.24932(17) 0.36965(14) 0.50660(7) 0.0363(4) Uani 1 1 d . . . . .
N5 N 0.28249(19) 0.16140(15) 0.49571(8) 0.0418(4) Uani 1 1 d . . . . .
O1 O 0.4450(2) 0.6626(2) 0.88451(9) 0.0987(8) Uani 1 1 d . . . . .
O2 O 0.6142(2) 0.6735(2) 0.82772(10) 0.0867(6) Uani 1 1 d . . . . .
O3 O 0.27043(19) 0.67082(14) 0.56667(8) 0.0608(5) Uani 1 1 d . . . . .
O4 O 0.4080(2) 0.04630(15) 0.57662(8) 0.0644(5) Uani 1 1 d . . . . .
S1 S 0.42541(6) 0.28058(5) 0.60669(2) 0.04444(17) 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 1.401(3) . ?
C1 C7 1.436(3) . ?
C1 N1 1.464(3) . ?
C2 C3 1.394(3) . ?
C2 H14 0.9300 . ?
C3 C5 1.419(3) . ?
C3 C4 1.523(3) . ?
C4 H15 0.9600 . ?
C4 H16 0.9600 . ?
C4 H17 0.9600 . ?
C5 C6 1.393(3) . ?
C5 H18 0.9300 . ?
C6 C7 1.437(3) . ?
C6 C8 1.540(3) . ?
C7 N2 1.377(3) . ?
C8 N3 1.503(2) . ?
C8 C9 1.549(3) . ?
C8 S1 1.893(2) . ?
C9 C10 1.520(3) . ?
C9 H3 0.9700 . ?
C9 H19 0.9700 . ?
C10 N2 1.469(3) . ?
C10 H20 0.9700 . ?
C10 H21 0.9700 . ?
C11 O3 1.242(3) . ?
C11 N3 1.390(3) . ?
C11 C12 1.519(3) . ?
C12 H11 0.9600 . ?
C12 H12 0.9600 . ?
C12 H13 0.9600 . ?
C13 N4 1.295(2) . ?
C13 N5 1.418(3) . ?
C13 S1 1.779(2) . ?
C14 O4 1.235(3) . ?
C14 N5 1.404(3) . ?
C14 C15 1.517(3) . ?
C15 H4 0.9600 . ?
C15 H5 0.9600 . ?
C15 H6 0.9600 . ?
C16 C17 1.392(3) . ?
C16 C21 1.398(3) . ?
C16 N5 1.471(3) . ?
C17 C18 1.410(4) . ?
C17 H10 0.9300 . ?
C18 C19 1.389(5) . ?
C18 H9 0.9300 . ?
C19 C20 1.386(5) . ?
C19 H2 0.9300 . ?
C20 C21 1.399(4) . ?
C20 H8 0.9300 . ?
C21 H7 0.9300 . ?
N1 O1 1.243(3) . ?
N1 O2 1.264(3) . ?
N2 H22 0.8600 . ?
N3 N4 1.409(2) . ?

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 C7 122.19(19) . . ?
C2 C1 N1 116.13(19) . . ?
C7 C1 N1 121.6(2) . . ?
C3 C2 C1 121.6(2) . . ?
C3 C2 H14 119.2 . . ?
C1 C2 H14 119.2 . . ?
C2 C3 C5 116.8(2) . . ?
C2 C3 C4 121.8(2) . . ?
C5 C3 C4 121.4(2) . . ?
C3 C4 H15 109.5 . . ?
C3 C4 H16 109.5 . . ?
H15 C4 H16 109.5 . . ?
C3 C4 H17 109.5 . . ?
H15 C4 H17 109.5 . . ?
H16 C4 H17 109.5 . . ?
C6 C5 C3 123.2(2) . . ?
C6 C5 H18 118.4 . . ?
C3 C5 H18 118.4 . . ?
C5 C6 C7 120.38(18) . . ?
C5 C6 C8 119.77(17) . . ?
C7 C6 C8 119.83(18) . . ?
N2 C7 C1 123.84(19) . . ?
N2 C7 C6 120.35(18) . . ?
C1 C7 C6 115.81(19) . . ?
N3 C8 C6 112.57(16) . . ?
N3 C8 C9 110.04(15) . . ?
C6 C8 C9 112.38(17) . . ?
N3 C8 S1 102.35(12) . . ?
C6 C8 S1 108.70(13) . . ?
C9 C8 S1 110.34(15) . . ?
C10 C9 C8 110.17(17) . . ?
C10 C9 H3 109.6 . . ?
C8 C9 H3 109.6 . . ?
C10 C9 H19 109.6 . . ?
C8 C9 H19 109.6 . . ?
H3 C9 H19 108.1 . . ?
N2 C10 C9 109.90(19) . . ?
N2 C10 H20 109.7 . . ?
C9 C10 H20 109.7 . . ?
N2 C10 H21 109.7 . . ?
C9 C10 H21 109.7 . . ?
H20 C10 H21 108.2 . . ?
O3 C11 N3 119.75(18) . . ?
O3 C11 C12 122.2(2) . . ?
N3 C11 C12 118.01(19) . . ?
C11 C12 H11 109.5 . . ?
C11 C12 H12 109.5 . . ?
H11 C12 H12 109.5 . . ?
C11 C12 H13 109.5 . . ?
H11 C12 H13 109.5 . . ?
H12 C12 H13 109.5 . . ?
N4 C13 N5 119.45(17) . . ?
N4 C13 S1 118.07(15) . . ?
N5 C13 S1 122.48(14) . . ?
O4 C14 N5 120.1(2) . . ?
O4 C14 C15 122.9(2) . . ?
N5 C14 C15 117.0(2) . . ?
C14 C15 H4 109.5 . . ?
C14 C15 H5 109.5 . . ?
H4 C15 H5 109.5 . . ?
C14 C15 H6 109.5 . . ?
H4 C15 H6 109.5 . . ?
H5 C15 H6 109.5 . . ?
C17 C16 C21 121.1(2) . . ?
C17 C16 N5 120.0(2) . . ?
C21 C16 N5 118.9(2) . . ?
C16 C17 C18 119.1(3) . . ?
C16 C17 H10 120.4 . . ?
C18 C17 H10 120.4 . . ?
C19 C18 C17 119.7(3) . . ?
C19 C18 H9 120.1 . . ?
C17 C18 H9 120.1 . . ?
C20 C19 C18 120.8(3) . . ?
C20 C19 H2 119.6 . . ?
C18 C19 H2 119.6 . . ?
C19 C20 C21 120.2(3) . . ?
C19 C20 H8 119.9 . . ?
C21 C20 H8 119.9 . . ?
C16 C21 C20 119.1(3) . . ?
C16 C21 H7 120.4 . . ?
C20 C21 H7 120.4 . . ?
O1 N1 O2 121.1(2) . . ?
O1 N1 C1 119.1(2) . . ?
O2 N1 C1 119.7(2) . . ?
C7 N2 C10 121.38(18) . . ?
C7 N2 H22 119.3 . . ?
C10 N2 H22 119.3 . . ?
C11 N3 N4 119.83(15) . . ?
C11 N3 C8 121.85(16) . . ?
N4 N3 C8 117.74(15) . . ?
C13 N4 N3 111.34(15) . . ?
C14 N5 C13 121.97(17) . . ?
C14 N5 C16 122.38(17) . . ?
C13 N5 C16 115.64(16) . . ?
C13 S1 C8 89.59(9) . . ?

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
C7 C1 C2 C3 -0.4(4) . . . . ?
N1 C1 C2 C3 -177.7(2) . . . . ?
C1 C2 C3 C5 -0.8(4) . . . . ?
C1 C2 C3 C4 178.0(3) . . . . ?
C2 C3 C5 C6 0.2(4) . . . . ?
C4 C3 C5 C6 -178.6(2) . . . . ?
C3 C5 C6 C7 1.8(3) . . . . ?
C3 C5 C6 C8 -179.9(2) . . . . ?
C2 C1 C7 N2 -176.8(2) . . . . ?
N1 C1 C7 N2 0.3(3) . . . . ?
C2 C1 C7 C6 2.3(3) . . . . ?
N1 C1 C7 C6 179.41(19) . . . . ?
C5 C6 C7 N2 176.3(2) . . . . ?
C8 C6 C7 N2 -2.0(3) . . . . ?
C5 C6 C7 C1 -2.9(3) . . . . ?
C8 C6 C7 C1 178.83(18) . . . . ?
C5 C6 C8 N3 40.7(3) . . . . ?
C7 C6 C8 N3 -140.95(18) . . . . ?
C5 C6 C8 C9 165.66(19) . . . . ?
C7 C6 C8 C9 -16.0(3) . . . . ?
C5 C6 C8 S1 -71.9(2) . . . . ?
C7 C6 C8 S1 106.40(18) . . . . ?
N3 C8 C9 C10 171.91(18) . . . . ?
C6 C8 C9 C10 45.6(3) . . . . ?
S1 C8 C9 C10 -75.9(2) . . . . ?
C8 C9 C10 N2 -58.1(3) . . . . ?
C21 C16 C17 C18 -1.3(4) . . . . ?
N5 C16 C17 C18 175.5(2) . . . . ?
C16 C17 C18 C19 0.7(4) . . . . ?
C17 C18 C19 C20 1.1(5) . . . . ?
C18 C19 C20 C21 -2.2(5) . . . . ?
C17 C16 C21 C20 0.2(4) . . . . ?
N5 C16 C21 C20 -176.6(2) . . . . ?
C19 C20 C21 C16 1.6(4) . . . . ?
C2 C1 N1 O1 2.8(3) . . . . ?
C7 C1 N1 O1 -174.5(2) . . . . ?
C2 C1 N1 O2 -178.7(2) . . . . ?
C7 C1 N1 O2 4.0(3) . . . . ?
C1 C7 N2 C10 167.2(2) . . . . ?
C6 C7 N2 C10 -11.9(3) . . . . ?
C9 C10 N2 C7 42.7(3) . . . . ?
O3 C11 N3 N4 -177.55(18) . . . . ?
C12 C11 N3 N4 2.3(3) . . . . ?
O3 C11 N3 C8 -6.5(3) . . . . ?
C12 C11 N3 C8 173.40(18) . . . . ?
C6 C8 N3 C11 62.0(2) . . . . ?
C9 C8 N3 C11 -64.2(2) . . . . ?
S1 C8 N3 C11 178.49(15) . . . . ?
C6 C8 N3 N4 -126.75(17) . . . . ?
C9 C8 N3 N4 107.06(19) . . . . ?
S1 C8 N3 N4 -10.24(18) . . . . ?
N5 C13 N4 N3 178.61(15) . . . . ?
S1 C13 N4 N3 -0.7(2) . . . . ?
C11 N3 N4 C13 179.27(17) . . . . ?
C8 N3 N4 C13 7.8(2) . . . . ?
O4 C14 N5 C13 -5.9(3) . . . . ?
C15 C14 N5 C13 174.1(2) . . . . ?
O4 C14 N5 C16 175.2(2) . . . . ?
C15 C14 N5 C16 -4.8(3) . . . . ?
N4 C13 N5 C14 -171.19(19) . . . . ?
S1 C13 N5 C14 8.1(3) . . . . ?
N4 C13 N5 C16 7.8(3) . . . . ?
S1 C13 N5 C16 -172.92(14) . . . . ?
C17 C16 N5 C14 101.5(3) . . . . ?
C21 C16 N5 C14 -81.7(3) . . . . ?
C17 C16 N5 C13 -77.5(3) . . . . ?
C21 C16 N5 C13 99.4(2) . . . . ?
N4 C13 S1 C8 -4.58(16) . . . . ?
N5 C13 S1 C8 176.13(16) . . . . ?
N3 C8 S1 C13 7.54(12) . . . . ?
C6 C8 S1 C13 126.80(14) . . . . ?
C9 C8 S1 C13 -109.55(14) . . . . ?

_refine_diff_density_max         0.254
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.040

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_shelx_CCDC5
_database_code_depnum_ccdc_archive 'CCDC 1980268'
loop_
_audit_author_name
_audit_author_address
'S Athimoolam'
;University College of Engineering, Anna University, Nagercoil
India
;
_audit_update_record             
;
2020-01-28 deposited with the CCDC.	2021-12-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H17 Cl N5 O4 S'
_chemical_formula_sum            'C16 H17 Cl N5 O4 S'
_chemical_formula_weight         410.85

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   26.56(3)
_cell_length_b                   6.708(6)
_cell_length_c                   20.85(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.285(17)
_cell_angle_gamma                90
_cell_volume                     3709(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2610
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      23.10

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    none
_exptl_crystal_density_diffrn    1.472
_exptl_crystal_F_000             1704
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.17
_exptl_absorpt_coefficient_mu    0.352
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6258
_exptl_special_details           
;
 The following wavelength and cell were deduced by SADABS from the
 direction cosines etc. They are given here for emergency use only:
 CELL 0.71074   26.528    6.699   20.830   89.945   93.360   89.974
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12115
_diffrn_reflns_av_unetI/netI     0.0380
_diffrn_reflns_av_R_equivalents  0.0412
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.418
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.971
_reflns_number_total             3255
_reflns_number_gt                2491
_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       'SMART (Bruker, 2001)'
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2015)'
_computing_structure_refinement  SHELXL-2014
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  SHELXL-2014

_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)+(0.0656P)²+11.3121P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3255
_refine_ls_number_parameters     250
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0791
_refine_ls_R_factor_gt           0.0578
_refine_ls_wR_factor_ref         0.1553
_refine_ls_wR_factor_gt          0.1422
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_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
C1 C 0.23410(11) 0.8142(5) 0.40329(17) 0.0364(8) Uani 1 1 d . . . . .
C2 C 0.25484(13) 0.9504(5) 0.44733(18) 0.0415(9) Uani 1 1 d . . . . .
H10 H 0.2341 1.0333 0.4699 0.050 Uiso 1 1 calc R U . . .
C3 C 0.30604(12) 0.9618(5) 0.45722(17) 0.0375(8) Uani 1 1 d . . . . .
C4 C 0.33705(11) 0.8446(5) 0.42185(16) 0.0353(8) Uani 1 1 d . . . . .
H9 H 0.3718 0.8577 0.4280 0.042 Uiso 1 1 calc R U . . .
C5 C 0.31742(11) 0.7092(5) 0.37784(15) 0.0309(7) Uani 1 1 d . . . . .
C6 C 0.26421(11) 0.6814(5) 0.36836(16) 0.0330(7) Uani 1 1 d . . . . .
C7 C 0.35324(11) 0.5921(5) 0.33699(16) 0.0338(8) Uani 1 1 d . . . . .
C8 C 0.32537(12) 0.4854(6) 0.28089(18) 0.0431(9) Uani 1 1 d . . . . .
H13 H 0.3167 0.5805 0.2470 0.052 Uiso 1 1 calc R U . . .
H14 H 0.3471 0.3848 0.2638 0.052 Uiso 1 1 calc R U . . .
C9 C 0.27818(13) 0.3887(6) 0.3024(2) 0.0480(10) Uani 1 1 d . . . . .
H11 H 0.2607 0.3226 0.2663 0.058 Uiso 1 1 calc R U . . .
H12 H 0.2869 0.2891 0.3349 0.058 Uiso 1 1 calc R U . . .
C10 C 0.38383(12) 0.8912(5) 0.27995(17) 0.0388(8) Uani 1 1 d . . . . .
C11 C 0.42822(13) 1.0123(6) 0.2618(2) 0.0508(10) Uani 1 1 d . . . . .
H6 H 0.4509 0.9294 0.2395 0.076 Uiso 1 1 calc R U . . .
H7 H 0.4454 1.0648 0.2999 0.076 Uiso 1 1 calc R U . . .
H8 H 0.4168 1.1203 0.2345 0.076 Uiso 1 1 calc R U . . .
C12 C 0.44526(12) 0.5122(5) 0.36604(18) 0.0406(9) Uani 1 1 d . . . . .
C13 C 0.49570(13) 0.2725(6) 0.4278(2) 0.0514(10) Uani 1 1 d . . . . .
C14 C 0.54680(15) 0.2095(8) 0.4556(3) 0.0817(17) Uani 1 1 d . . . . .
H15 H 0.5643 0.3232 0.4738 0.123 Uiso 1 1 calc R U . . .
H16 H 0.5659 0.1537 0.4222 0.123 Uiso 1 1 calc R U . . .
H17 H 0.5428 0.1113 0.4884 0.123 Uiso 1 1 calc R U . . .
C15 C 0.5424(2) 0.5285(9) 0.3511(4) 0.108(2) Uani 1 1 d . . . . .
H4 H 0.5709 0.4377 0.3518 0.130 Uiso 1 1 calc R U . . .
H5 H 0.5341 0.5758 0.3079 0.130 Uiso 1 1 calc R U . . .
C16 C 0.5478(3) 0.6725(15) 0.3938(3) 0.144(3) Uani 1 1 d . . . . .
H1 H 0.5258 0.6813 0.4269 0.173 Uiso 1 1 calc R U . . .
H3 H 0.5735 0.7656 0.3908 0.173 Uiso 1 1 calc R U . . .
N1 N 0.17981(10) 0.8116(5) 0.39481(16) 0.0493(8) Uani 1 1 d . . . . .
N2 N 0.24549(11) 0.5377(5) 0.32860(15) 0.0426(8) Uani 1 1 d . . . . .
N3 N 0.39372(9) 0.7220(4) 0.31478(14) 0.0349(7) Uani 1 1 d . . . . .
N4 N 0.44355(10) 0.6662(5) 0.32998(15) 0.0439(8) Uani 1 1 d . . . . .
N5 N 0.49201(11) 0.4362(5) 0.3882(2) 0.0707(12) Uani 1 1 d . . . . .
O1 O 0.15858(9) 0.7024(5) 0.35452(14) 0.0596(8) Uani 1 1 d . . . . .
O2 O 0.15579(10) 0.9218(6) 0.4289(2) 0.0930(13) Uani 1 1 d . . . . .
O3 O 0.34004(9) 0.9386(4) 0.26528(13) 0.0505(7) Uani 1 1 d . . . . .
O4 O 0.45822(10) 0.1820(5) 0.43955(17) 0.0770(11) Uani 1 1 d . . . . .
S1 S 0.38876(3) 0.40804(14) 0.38868(5) 0.0417(3) Uani 1 1 d . . . . .
Cl1 Cl 0.33226(4) 1.12619(16) 0.51438(5) 0.0574(3) Uani 1 1 d . . . . .
H2 H 0.2125(16) 0.532(6) 0.3214(19) 0.058(12) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.387(5) . ?
C1 C6 1.425(5) . ?
C1 N1 1.442(4) . ?
C2 C3 1.366(5) . ?
C2 H10 0.9300 . ?
C3 C4 1.382(5) . ?
C3 Cl1 1.739(4) . ?
C4 C5 1.373(5) . ?
C4 H9 0.9300 . ?
C5 C6 1.428(4) . ?
C5 C7 1.530(4) . ?
C6 N2 1.348(4) . ?
C7 N3 1.479(4) . ?
C7 C8 1.526(5) . ?
C7 S1 1.860(3) . ?
C8 C9 1.503(5) . ?
C8 H13 0.9700 . ?
C8 H14 0.9700 . ?
C9 N2 1.451(5) . ?
C9 H11 0.9700 . ?
C9 H12 0.9700 . ?
C10 O3 1.227(4) . ?
C10 N3 1.365(4) . ?
C10 C11 1.498(5) . ?
C11 H6 0.9600 . ?
C11 H7 0.9600 . ?
C11 H8 0.9600 . ?
C12 N4 1.277(5) . ?
C12 N5 1.396(4) . ?
C12 S1 1.745(4) . ?
C13 O4 1.203(5) . ?
C13 N5 1.375(5) . ?
C13 C14 1.505(5) . ?
C14 H15 0.9600 . ?
C14 H16 0.9600 . ?
C14 H17 0.9600 . ?
C15 C16 1.315(9) . ?
C15 N5 1.700(8) . ?
C15 H4 0.9700 . ?
C15 H5 0.9700 . ?
C16 H1 0.9300 . ?
C16 H3 0.9300 . ?
N1 O1 1.227(4) . ?
N1 O2 1.230(4) . ?
N2 H2 0.88(4) . ?
N3 N4 1.394(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 122.5(3) . . ?
C2 C1 N1 116.4(3) . . ?
C6 C1 N1 121.1(3) . . ?
C3 C2 C1 119.4(3) . . ?
C3 C2 H10 120.3 . . ?
C1 C2 H10 120.3 . . ?
C2 C3 C4 120.4(3) . . ?
C2 C3 Cl1 119.7(3) . . ?
C4 C3 Cl1 119.9(3) . . ?
C5 C4 C3 121.2(3) . . ?
C5 C4 H9 119.4 . . ?
C3 C4 H9 119.4 . . ?
C4 C5 C6 120.9(3) . . ?
C4 C5 C7 119.2(3) . . ?
C6 C5 C7 119.9(3) . . ?
N2 C6 C1 124.3(3) . . ?
N2 C6 C5 120.4(3) . . ?
C1 C6 C5 115.3(3) . . ?
N3 C7 C8 111.5(3) . . ?
N3 C7 C5 111.0(3) . . ?
C8 C7 C5 112.2(3) . . ?
N3 C7 S1 102.7(2) . . ?
C8 C7 S1 109.9(2) . . ?
C5 C7 S1 109.2(2) . . ?
C9 C8 C7 110.5(3) . . ?
C9 C8 H13 109.6 . . ?
C7 C8 H13 109.6 . . ?
C9 C8 H14 109.6 . . ?
C7 C8 H14 109.6 . . ?
H13 C8 H14 108.1 . . ?
N2 C9 C8 110.0(3) . . ?
N2 C9 H11 109.7 . . ?
C8 C9 H11 109.7 . . ?
N2 C9 H12 109.7 . . ?
C8 C9 H12 109.7 . . ?
H11 C9 H12 108.2 . . ?
O3 C10 N3 119.9(3) . . ?
O3 C10 C11 123.0(3) . . ?
N3 C10 C11 117.1(3) . . ?
C10 C11 H6 109.5 . . ?
C10 C11 H7 109.5 . . ?
H6 C11 H7 109.5 . . ?
C10 C11 H8 109.5 . . ?
H6 C11 H8 109.5 . . ?
H7 C11 H8 109.5 . . ?
N4 C12 N5 119.4(3) . . ?
N4 C12 S1 118.8(2) . . ?
N5 C12 S1 121.8(3) . . ?
O4 C13 N5 119.6(3) . . ?
O4 C13 C14 121.3(4) . . ?
N5 C13 C14 119.1(3) . . ?
C13 C14 H15 109.5 . . ?
C13 C14 H16 109.5 . . ?
H15 C14 H16 109.5 . . ?
C13 C14 H17 109.5 . . ?
H15 C14 H17 109.5 . . ?
H16 C14 H17 109.5 . . ?
C16 C15 N5 91.0(7) . . ?
C16 C15 H4 113.5 . . ?
N5 C15 H4 113.5 . . ?
C16 C15 H5 113.5 . . ?
N5 C15 H5 113.5 . . ?
H4 C15 H5 110.8 . . ?
C15 C16 H1 120.0 . . ?
C15 C16 H3 120.0 . . ?
H1 C16 H3 120.0 . . ?
O1 N1 O2 121.4(3) . . ?
O1 N1 C1 120.5(3) . . ?
O2 N1 C1 118.0(3) . . ?
C6 N2 C9 121.1(3) . . ?
C6 N2 H2 118(3) . . ?
C9 N2 H2 121(3) . . ?
C10 N3 N4 119.7(3) . . ?
C10 N3 C7 122.4(3) . . ?
N4 N3 C7 117.9(3) . . ?
C12 N4 N3 110.6(3) . . ?
C13 N5 C12 121.5(3) . . ?
C13 N5 C15 122.2(3) . . ?
C12 N5 C15 115.1(3) . . ?
C12 S1 C7 89.60(16) . . ?

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
C6 C1 C2 C3 1.2(5) . . . . ?
N1 C1 C2 C3 -179.4(3) . . . . ?
C1 C2 C3 C4 2.6(5) . . . . ?
C1 C2 C3 Cl1 -177.8(3) . . . . ?
C2 C3 C4 C5 -2.4(5) . . . . ?
Cl1 C3 C4 C5 178.0(3) . . . . ?
C3 C4 C5 C6 -1.6(5) . . . . ?
C3 C4 C5 C7 176.3(3) . . . . ?
C2 C1 C6 N2 175.1(3) . . . . ?
N1 C1 C6 N2 -4.3(5) . . . . ?
C2 C1 C6 C5 -4.9(5) . . . . ?
N1 C1 C6 C5 175.7(3) . . . . ?
C4 C5 C6 N2 -175.0(3) . . . . ?
C7 C5 C6 N2 7.1(5) . . . . ?
C4 C5 C6 C1 5.1(5) . . . . ?
C7 C5 C6 C1 -172.9(3) . . . . ?
C4 C5 C7 N3 -41.5(4) . . . . ?
C6 C5 C7 N3 136.4(3) . . . . ?
C4 C5 C7 C8 -166.9(3) . . . . ?
C6 C5 C7 C8 11.0(4) . . . . ?
C4 C5 C7 S1 70.9(3) . . . . ?
C6 C5 C7 S1 -111.1(3) . . . . ?
N3 C7 C8 C9 -168.3(3) . . . . ?
C5 C7 C8 C9 -43.2(4) . . . . ?
S1 C7 C8 C9 78.6(3) . . . . ?
C7 C8 C9 N2 58.8(4) . . . . ?
C2 C1 N1 O1 176.4(3) . . . . ?
C6 C1 N1 O1 -4.2(5) . . . . ?
C2 C1 N1 O2 -3.4(5) . . . . ?
C6 C1 N1 O2 176.0(4) . . . . ?
C1 C6 N2 C9 -170.3(3) . . . . ?
C5 C6 N2 C9 9.7(5) . . . . ?
C8 C9 N2 C6 -43.2(5) . . . . ?
O3 C10 N3 N4 178.4(3) . . . . ?
C11 C10 N3 N4 -2.1(5) . . . . ?
O3 C10 N3 C7 -1.0(5) . . . . ?
C11 C10 N3 C7 178.5(3) . . . . ?
C8 C7 N3 C10 68.8(4) . . . . ?
C5 C7 N3 C10 -57.0(4) . . . . ?
S1 C7 N3 C10 -173.6(3) . . . . ?
C8 C7 N3 N4 -110.6(3) . . . . ?
C5 C7 N3 N4 123.6(3) . . . . ?
S1 C7 N3 N4 7.0(3) . . . . ?
N5 C12 N4 N3 -178.1(4) . . . . ?
S1 C12 N4 N3 -0.5(4) . . . . ?
C10 N3 N4 C12 175.8(3) . . . . ?
C7 N3 N4 C12 -4.7(4) . . . . ?
O4 C13 N5 C12 6.3(7) . . . . ?
C14 C13 N5 C12 -174.0(5) . . . . ?
O4 C13 N5 C15 -160.8(5) . . . . ?
C14 C13 N5 C15 18.9(7) . . . . ?
N4 C12 N5 C13 179.1(4) . . . . ?
S1 C12 N5 C13 1.6(6) . . . . ?
N4 C12 N5 C15 -12.9(6) . . . . ?
S1 C12 N5 C15 169.5(3) . . . . ?
C16 C15 N5 C13 -101.6(5) . . . . ?
C16 C15 N5 C12 90.5(5) . . . . ?
N4 C12 S1 C7 3.9(3) . . . . ?
N5 C12 S1 C7 -178.5(4) . . . . ?
N3 C7 S1 C12 -5.5(2) . . . . ?
C8 C7 S1 C12 113.2(3) . . . . ?
C5 C7 S1 C12 -123.4(2) . . . . ?

_refine_diff_density_max         0.588
_refine_diff_density_min         -0.471
_refine_diff_density_rms         0.066

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_shelx_CCDC6
_database_code_depnum_ccdc_archive 'CCDC 1980267'
loop_
_audit_author_name
_audit_author_address
'S Athimoolam'
;University College of Engineering Anna University Nagercoil 
India
;
_audit_update_record             
;
2020-01-28 deposited with the CCDC.	2021-12-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C56 H52 Cl4 N20 O16 S4'
_chemical_formula_sum            'C56 H52 Cl4 N20 O16 S4'
_chemical_formula_weight         1531.21

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                   12.294(7)
_cell_length_b                   16.369(7)
_cell_length_c                   18.699(10)
_cell_angle_alpha                104.620(9)
_cell_angle_beta                 105.192(12)
_cell_angle_gamma                100.914(9)
_cell_volume                     3380(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2356
_cell_measurement_theta_min      2.24
_cell_measurement_theta_max      24.82

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    none
_exptl_crystal_density_diffrn    1.505
_exptl_crystal_F_000             1576
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_absorpt_coefficient_mu    0.380
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.7030

_exptl_special_details           
;
 The following wavelength and cell were deduced by SADABS from the
 direction cosines etc. They are given here for emergency use only:
 CELL 0.71055   12.294   16.356   18.697  104.739  105.181  100.934
;


_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            65269
_diffrn_reflns_av_unetI/netI     0.0455
_diffrn_reflns_av_R_equivalents  0.0644
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.171
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.972
_reflns_number_total             11902
_reflns_number_gt                8678
_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       'SMART (Bruker, 2001)'
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2015)'
_computing_structure_refinement  SHELXL-2014
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  SHELXL-2014

_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)+(0.0709P)²+3.7135P] 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         11902
_refine_ls_number_parameters     909
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0831
_refine_ls_R_factor_gt           0.0552
_refine_ls_wR_factor_ref         0.1550
_refine_ls_wR_factor_gt          0.1387
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_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
C1A C 0.6823(4) -0.0640(3) 0.0078(2) 0.0532(10) Uani 1 1 d . . . . .
C1B C 0.5884(3) 0.0187(2) 0.6574(2) 0.0400(8) Uani 1 1 d . . . . .
C1C C 0.8203(3) 0.5699(2) 0.28033(19) 0.0351(8) Uani 1 1 d . . . . .
C1D C 0.7918(4) 0.5621(2) 0.9801(2) 0.0453(9) Uani 1 1 d . . . . .
C2A C 0.5786(4) -0.1013(3) 0.0189(2) 0.0518(10) Uani 1 1 d . . . . .
H46 H 0.5343 -0.1581 -0.0118 0.062 Uiso 1 1 calc R U . . .
C2B C 0.5450(3) 0.0790(2) 0.6270(2) 0.0393(8) Uani 1 1 d . . . . .
H9 H 0.4850 0.0990 0.6407 0.047 Uiso 1 1 calc R U . . .
C2C C 0.8883(3) 0.5120(2) 0.2875(2) 0.0427(9) Uani 1 1 d . . . . .
H29 H 0.9338 0.5017 0.2553 0.051 Uiso 1 1 calc R U . . .
C2D C 0.8993(4) 0.6045(2) 0.9768(2) 0.0488(10) Uani 1 1 d . . . . .
H21 H 0.9358 0.6630 1.0065 0.059 Uiso 1 1 calc R U . . .
C3A C 0.5430(3) -0.0540(2) 0.0749(2) 0.0442(9) Uani 1 1 d . . . . .
C3B C 0.5911(3) 0.1089(2) 0.5767(2) 0.0365(8) Uani 1 1 d . . . . .
C3C C 0.8882(3) 0.4704(2) 0.3418(2) 0.0465(9) Uani 1 1 d . . . . .
C3D C 0.9500(3) 0.5589(2) 0.9293(2) 0.0428(9) Uani 1 1 d . . . . .
C4A C 0.6099(3) 0.0307(2) 0.1213(2) 0.0387(8) Uani 1 1 d . . . . .
H47 H 0.5845 0.0624 0.1593 0.046 Uiso 1 1 calc R U . . .
C4B C 0.6820(3) 0.0800(2) 0.5572(2) 0.0360(8) Uani 1 1 d . . . . .
H10 H 0.7125 0.1009 0.5227 0.043 Uiso 1 1 calc R U . . .
C4C C 0.8179(3) 0.4838(2) 0.3884(2) 0.0414(9) Uani 1 1 d . . . . .
H34 H 0.8193 0.4554 0.4257 0.050 Uiso 1 1 calc R U . . .
C4D C 0.8931(3) 0.4729(2) 0.88284(19) 0.0362(8) Uani 1 1 d . . . . .
H20 H 0.9283 0.4428 0.8504 0.043 Uiso 1 1 calc R U . . .
C5A C 0.7132(3) 0.0682(2) 0.11194(19) 0.0331(7) Uani 1 1 d . . . . .
C5B C 0.7277(3) 0.0210(2) 0.58793(19) 0.0315(7) Uani 1 1 d . . . . .
C5C C 0.7463(3) 0.5381(2) 0.38033(19) 0.0296(7) Uani 1 1 d . . . . .
C5D C 0.7854(3) 0.4311(2) 0.88364(18) 0.0311(7) Uani 1 1 d . . . . .
C6A C 0.7531(3) 0.0223(2) 0.0531(2) 0.0399(8) Uani 1 1 d . . . . .
C6B C 0.6818(3) -0.0137(2) 0.6398(2) 0.0360(8) Uani 1 1 d . . . . .
C6C C 0.7462(3) 0.5863(2) 0.32629(18) 0.0293(7) Uani 1 1 d . . . . .
C6D C 0.7318(3) 0.4736(2) 0.93557(19) 0.0363(8) Uani 1 1 d . . . . .
C7A C 0.7832(3) 0.1613(2) 0.16100(19) 0.0341(7) Uani 1 1 d . . . . .
C7B C 0.7255(3) -0.0725(2) 0.66742(19) 0.0316(7) Uani 1 1 d . . . . .
H8 H 0.7041 -0.0869 0.7078 0.038 Uiso 1 1 calc R U . . .
C7C C 0.6172(3) 0.6647(2) 0.37523(19) 0.0331(7) Uani 1 1 d . . . . .
H36 H 0.5548 0.6883 0.3525 0.040 Uiso 1 1 calc R U . . .
H37 H 0.6698 0.7092 0.4232 0.040 Uiso 1 1 calc R U . . .
C7D C 0.7231(3) 0.3377(2) 0.83013(19) 0.0322(7) Uani 1 1 d . . . . .
C8A C 0.9119(3) 0.1757(3) 0.1681(2) 0.0455(9) Uani 1 1 d . . . . .
H49 H 0.9538 0.2369 0.1958 0.055 Uiso 1 1 calc R U . . .
H50 H 0.9460 0.1404 0.1974 0.055 Uiso 1 1 calc R U . . .
C8B C 0.8910(3) -0.0503(2) 0.6200(2) 0.0416(9) Uani 1 1 d . . . . .
H5 H 0.9416 -0.0798 0.5977 0.050 Uiso 1 1 calc R U . . .
H6 H 0.9395 -0.0042 0.6681 0.050 Uiso 1 1 calc R U . . .
C8C C 0.5664(3) 0.5842(2) 0.39284(19) 0.0316(7) Uani 1 1 d . . . . .
H32 H 0.5127 0.5401 0.3450 0.038 Uiso 1 1 calc R U . . .
H33 H 0.5231 0.5988 0.4286 0.038 Uiso 1 1 calc R U . . .
C8D C 0.5915(3) 0.3194(2) 0.8150(2) 0.0440(9) Uani 1 1 d . . . . .
H23 H 0.5602 0.3554 0.7853 0.053 Uiso 1 1 calc R U . . .
H24 H 0.5532 0.2582 0.7845 0.053 Uiso 1 1 calc R U . . .
C9A C 0.9226(3) 0.1501(3) 0.0873(2) 0.0528(10) Uani 1 1 d . . . . .
H48 H 0.9673 0.1866 0.0685 0.063 Uiso 1 1 calc R U . . .
C9B C 0.8248(3) -0.0104(2) 0.56262(19) 0.0321(7) Uani 1 1 d . . . . .
C9C C 0.6648(3) 0.5483(2) 0.42933(18) 0.0293(7) Uani 1 1 d . . . . .
C9D C 0.5677(3) 0.3397(3) 0.8918(2) 0.0513(10) Uani 1 1 d . . . . .
H19 H 0.5206 0.3002 0.9067 0.062 Uiso 1 1 calc R U . . .
C10A C 0.8001(3) 0.1518(2) 0.2945(2) 0.0392(8) Uani 1 1 d . . . . .
C10B C 0.9678(3) 0.1372(2) 0.6045(2) 0.0367(8) Uani 1 1 d . . . . .
C10C C 0.5552(3) 0.3902(2) 0.3837(2) 0.0340(8) Uani 1 1 d . . . . .
C10D C 0.7400(3) 0.3671(2) 0.70772(19) 0.0335(8) Uani 1 1 d . . . . .
C11A C 0.7762(4) 0.1866(3) 0.3692(2) 0.0595(11) Uani 1 1 d . . . . .
H52 H 0.8042 0.1560 0.4046 0.089 Uiso 1 1 calc R U . . .
H53 H 0.6933 0.1781 0.3585 0.089 Uiso 1 1 calc R U . . .
H54 H 0.8156 0.2482 0.3924 0.089 Uiso 1 1 calc R U . . .
C11B C 1.0227(3) 0.2104(2) 0.5803(2) 0.0505(10) Uani 1 1 d . . . . .
H11 H 1.0082 0.1904 0.5249 0.076 Uiso 1 1 calc R U . . .
H12 H 1.1056 0.2293 0.6072 0.076 Uiso 1 1 calc R U . . .
H13 H 0.9896 0.2585 0.5933 0.076 Uiso 1 1 calc R U . . .
C11C C 0.5172(4) 0.3088(2) 0.4033(2) 0.0515(10) Uani 1 1 d . . . . .
H38 H 0.4505 0.3109 0.4207 0.077 Uiso 1 1 calc R U . . .
H39 H 0.5801 0.3048 0.4441 0.077 Uiso 1 1 calc R U . . .
H40 H 0.4963 0.2585 0.3578 0.077 Uiso 1 1 calc R U . . .
C11D C 0.7966(3) 0.3515(3) 0.6458(2) 0.0474(9) Uani 1 1 d . . . . .
H25 H 0.7772 0.2896 0.6193 0.071 Uiso 1 1 calc R U . . .
H26 H 0.8801 0.3742 0.6694 0.071 Uiso 1 1 calc R U . . .
H27 H 0.7690 0.3806 0.6090 0.071 Uiso 1 1 calc R U . . .
C12A C 0.6767(3) 0.2778(2) 0.19187(19) 0.0353(8) Uani 1 1 d . . . . .
C12B C 0.8220(3) -0.0227(2) 0.42428(19) 0.0275(7) Uani 1 1 d . . . . .
C12C C 0.6977(3) 0.5427(2) 0.56773(19) 0.0313(7) Uani 1 1 d . . . . .
C12D C 0.8377(3) 0.2272(2) 0.80259(19) 0.0364(8) Uani 1 1 d . . . . .
C13A C 0.5835(4) 0.3744(3) 0.1340(2) 0.0481(9) Uani 1 1 d . . . . .
C13B C 0.7318(3) -0.1235(2) 0.2914(2) 0.0332(7) Uani 1 1 d . . . . .
C13C C 0.7747(3) 0.6401(3) 0.7033(2) 0.0464(9) Uani 1 1 d . . . . .
C13D C 0.9274(4) 0.1280(3) 0.8596(2) 0.0562(11) Uani 1 1 d . . . . .
C14A C 0.5090(4) 0.4358(3) 0.1458(3) 0.0687(13) Uani 1 1 d . . . . .
H44 H 0.5239 0.4619 0.2007 0.103 Uiso 1 1 calc R U . . .
H45 H 0.4278 0.4039 0.1210 0.103 Uiso 1 1 calc R U . . .
H55 H 0.5274 0.4810 0.1232 0.103 Uiso 1 1 calc R U . . .
C14B C 0.7170(4) -0.1336(3) 0.2080(2) 0.0534(10) Uani 1 1 d . . . . .
H1 H 0.6351 -0.1538 0.1781 0.080 Uiso 1 1 calc R U . . .
H3 H 0.7560 -0.1755 0.1886 0.080 Uiso 1 1 calc R U . . .
H4 H 0.7503 -0.0780 0.2033 0.080 Uiso 1 1 calc R U . . .
C14C C 0.7838(4) 0.6428(3) 0.7850(2) 0.0698(13) Uani 1 1 d . . . . .
H30 H 0.7448 0.6840 0.8058 0.105 Uiso 1 1 calc R U . . .
H31 H 0.8649 0.6608 0.8166 0.105 Uiso 1 1 calc R U . . .
H42 H 0.7476 0.5856 0.7852 0.105 Uiso 1 1 calc R U . . .
C14D C 1.0055(5) 0.0695(4) 0.8517(3) 0.0925(19) Uani 1 1 d . . . . .
H16 H 0.9707 0.0144 0.8566 0.139 Uiso 1 1 calc R U . . .
H17 H 1.0802 0.0966 0.8919 0.139 Uiso 1 1 calc R U . . .
H18 H 1.0159 0.0598 0.8014 0.139 Uiso 1 1 calc R U . . .
N11 N 0.7128(4) -0.1180(3) -0.0540(3) 0.0886(14) Uani 1 1 d . . . . .
N12 N 0.8535(3) 0.0607(2) 0.04321(19) 0.0516(8) Uani 1 1 d . . . . .
H51 H 0.8775 0.0303 0.0089 0.062 Uiso 1 1 calc R U . . .
N13 N 0.7648(2) 0.18814(17) 0.23805(16) 0.0344(6) Uani 1 1 d . . . . .
N14 N 0.7008(3) 0.24962(18) 0.25032(16) 0.0387(7) Uani 1 1 d . . . . .
N15 N 0.6116(3) 0.33807(19) 0.19229(17) 0.0419(7) Uani 1 1 d . . . . .
N21 N 0.5282(3) -0.0158(2) 0.7052(2) 0.0576(9) Uani 1 1 d . . . . .
N22 N 0.8048(4) -0.1150(3) 0.6370(2) 0.0747(11) Uani 1 1 d . . . . .
H7 H 0.8029 -0.1694 0.6298 0.090 Uiso 1 1 calc R U . . .
N23 N 0.9019(2) 0.06004(17) 0.54763(15) 0.0305(6) Uani 1 1 d . . . . .
N24 N 0.8903(2) 0.05209(17) 0.46971(15) 0.0304(6) Uani 1 1 d . . . . .
N25 N 0.8000(2) -0.04379(17) 0.34462(15) 0.0322(6) Uani 1 1 d . . . . .
H14 H 0.8308 -0.0046 0.3272 0.039 Uiso 1 1 calc R U . . .
N31 N 0.8313(3) 0.6154(2) 0.22420(18) 0.0487(8) Uani 1 1 d . . . . .
N32 N 0.6802(2) 0.64253(18) 0.32137(16) 0.0355(6) Uani 1 1 d . . . . .
H35 H 0.6753 0.6661 0.2848 0.043 Uiso 1 1 calc R U . . .
N33 N 0.6207(2) 0.46482(17) 0.44312(15) 0.0315(6) Uani 1 1 d . . . . .
N34 N 0.6373(2) 0.46739(18) 0.52036(16) 0.0341(6) Uani 1 1 d . . . . .
N35 N 0.7226(2) 0.55918(19) 0.64744(16) 0.0395(7) Uani 1 1 d . . . . .
H41 H 0.7039 0.5152 0.6633 0.047 Uiso 1 1 calc R U . . .
N41 N 0.7409(4) 0.6162(3) 1.02929(19) 0.0633(10) Uani 1 1 d . . . . .
N42 N 0.6288(3) 0.4297(2) 0.93890(18) 0.0464(8) Uani 1 1 d . . . . .
H22 H 0.5984 0.4568 0.9708 0.056 Uiso 1 1 calc R U . . .
N43 N 0.7543(2) 0.31886(17) 0.75713(15) 0.0319(6) Uani 1 1 d . . . . .
N44 N 0.8208(3) 0.25945(19) 0.74676(16) 0.0389(7) Uani 1 1 d . . . . .
N45 N 0.9046(3) 0.1684(2) 0.80420(18) 0.0529(9) Uani 1 1 d . . . . .
H28 H 0.9342 0.1563 0.7672 0.063 Uiso 1 1 calc R U . . .
O11 O 0.6492(5) -0.1920(3) -0.0908(3) 0.145(2) Uani 1 1 d . . . . .
O12 O 0.8020(4) -0.0893(3) -0.0677(3) 0.1225(17) Uani 1 1 d . . . . .
O13 O 0.8501(2) 0.09323(16) 0.28322(15) 0.0463(6) Uani 1 1 d . . . . .
O14 O 0.6158(3) 0.3575(2) 0.07817(19) 0.0797(10) Uani 1 1 d . . . . .
O21 O 0.5629(3) -0.0684(3) 0.7353(2) 0.0877(11) Uani 1 1 d . . . . .
O22 O 0.4428(3) 0.0078(3) 0.7132(2) 0.0862(11) Uani 1 1 d . . . . .
O23 O 0.9802(2) 0.14528(18) 0.67342(15) 0.0555(7) Uani 1 1 d . . . . .
O24 O 0.6867(2) -0.18143(15) 0.31296(14) 0.0466(6) Uani 1 1 d . . . . .
O31 O 0.8977(3) 0.6008(3) 0.1874(2) 0.0855(11) Uani 1 1 d . . . . .
O32 O 0.7763(3) 0.6694(2) 0.21673(18) 0.0705(9) Uani 1 1 d . . . . .
O33 O 0.5296(2) 0.39074(16) 0.31584(14) 0.0445(6) Uani 1 1 d . . . . .
O34 O 0.8101(3) 0.70370(18) 0.68567(16) 0.0664(8) Uani 1 1 d . . . . .
O41 O 0.7834(4) 0.6960(2) 1.0537(2) 0.0961(13) Uani 1 1 d . . . . .
O42 O 0.6551(3) 0.5803(3) 1.04381(19) 0.0836(11) Uani 1 1 d . . . . .
O43 O 0.6850(2) 0.42234(16) 0.71564(14) 0.0439(6) Uani 1 1 d . . . . .
O44 O 0.8865(4) 0.1398(2) 0.9121(2) 0.0861(11) Uani 1 1 d . . . . .
S1 S 0.72384(9) 0.23807(6) 0.11345(5) 0.0422(2) Uani 1 1 d . . . . .
S2 S 0.75784(7) -0.09556(5) 0.46480(5) 0.0347(2) Uani 1 1 d . . . . .
S3 S 0.74808(8) 0.62458(6) 0.52998(5) 0.0384(2) Uani 1 1 d . . . . .
S4 S 0.77897(9) 0.25939(6) 0.87658(5) 0.0444(2) Uani 1 1 d . . . . .
Cl1 Cl 0.41450(10) -0.09866(7) 0.08969(7) 0.0667(3) Uani 1 1 d . . . . .
Cl2 Cl 0.53544(8) 0.18208(6) 0.53421(7) 0.0560(3) Uani 1 1 d . . . . .
Cl3 Cl 0.97792(10) 0.40127(8) 0.35424(9) 0.0791(4) Uani 1 1 d . . . . .
Cl4 Cl 1.08258(10) 0.60842(7) 0.92156(6) 0.0668(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
C1A C2A 1.396(6) . ?
C1A C6A 1.419(5) . ?
C1A N11 1.447(5) . ?
C1B C2B 1.382(5) . ?
C1B C6B 1.431(5) . ?
C1B N21 1.451(5) . ?
C1C C2C 1.386(5) . ?
C1C C6C 1.423(4) . ?
C1C N31 1.452(5) . ?
C1D C2D 1.396(6) . ?
C1D C6D 1.415(5) . ?
C1D N41 1.457(5) . ?
C2A C3A 1.360(5) . ?
C2A H46 0.9300 . ?
C2B C3B 1.360(5) . ?
C2B H9 0.9300 . ?
C2C C3C 1.357(5) . ?
C2C H29 0.9300 . ?
C2D C3D 1.367(5) . ?
C2D H21 0.9300 . ?
C3A C4A 1.392(5) . ?
C3A Cl1 1.732(4) . ?
C3B C4B 1.390(4) . ?
C3B Cl2 1.744(3) . ?
C3C C4C 1.387(5) . ?
C3C Cl3 1.739(4) . ?
C3D C4D 1.384(5) . ?
C3D Cl4 1.737(4) . ?
C4A C5A 1.377(5) . ?
C4A H47 0.9300 . ?
C4B C5B 1.376(5) . ?
C4B H10 0.9300 . ?
C4C C5C 1.372(5) . ?
C4C H34 0.9300 . ?
C4D C5D 1.376(5) . ?
C4D H20 0.9300 . ?
C5A C6A 1.421(5) . ?
C5A C7A 1.512(5) . ?
C5B C6B 1.423(5) . ?
C5B C9B 1.523(4) . ?
C5C C6C 1.430(4) . ?
C5C C9C 1.529(4) . ?
C5D C6D 1.425(5) . ?
C5D C7D 1.519(5) . ?
C6A N12 1.356(5) . ?
C6B C7B 1.336(5) . ?
C6C N32 1.343(4) . ?
C6D N42 1.357(5) . ?
C7A N13 1.486(4) . ?
C7A C8A 1.520(5) . ?
C7A S1 1.864(3) . ?
C7B N22 1.452(5) . ?
C7B H8 0.9300 . ?
C7C N32 1.441(4) . ?
C7C C8C 1.499(4) . ?
C7C H36 0.9700 . ?
C7C H37 0.9700 . ?
C7D N43 1.487(4) . ?
C7D C8D 1.523(5) . ?
C7D S4 1.858(3) . ?
C8A C9A 1.510(5) . ?
C8A H49 0.9700 . ?
C8A H50 0.9700 . ?
C8B N22 1.506(5) . ?
C8B C9B 1.528(5) . ?
C8B H5 0.9700 . ?
C8B H6 0.9700 . ?
C8C C9C 1.521(4) . ?
C8C H32 0.9700 . ?
C8C H33 0.9700 . ?
C8D C9D 1.509(5) . ?
C8D H23 0.9700 . ?
C8D H24 0.9700 . ?
C9A N12 1.448(5) . ?
C9A H48 0.9300 . ?
C9B N23 1.482(4) . ?
C9B S2 1.859(3) . ?
C9C N33 1.483(4) . ?
C9C S3 1.863(3) . ?
C9D N42 1.444(5) . ?
C9D H19 0.9300 . ?
C10A O13 1.237(4) . ?
C10A N13 1.353(4) . ?
C10A C11A 1.496(5) . ?
C10B O23 1.227(4) . ?
C10B N23 1.366(4) . ?
C10B C11B 1.490(5) . ?
C10C O33 1.227(4) . ?
C10C N33 1.360(4) . ?
C10C C11C 1.492(5) . ?
C10D O43 1.231(4) . ?
C10D N43 1.357(4) . ?
C10D C11D 1.493(5) . ?
C11A H52 0.9600 . ?
C11A H53 0.9600 . ?
C11A H54 0.9600 . ?
C11B H11 0.9600 . ?
C11B H12 0.9600 . ?
C11B H13 0.9600 . ?
C11C H38 0.9600 . ?
C11C H39 0.9600 . ?
C11C H40 0.9600 . ?
C11D H25 0.9600 . ?
C11D H26 0.9600 . ?
C11D H27 0.9600 . ?
C12A N14 1.278(4) . ?
C12A N15 1.383(4) . ?
C12A S1 1.737(3) . ?
C12B N24 1.280(4) . ?
C12B N25 1.380(4) . ?
C12B S2 1.741(3) . ?
C12C N34 1.270(4) . ?
C12C N35 1.384(4) . ?
C12C S3 1.752(3) . ?
C12D N44 1.272(4) . ?
C12D N45 1.380(4) . ?
C12D S4 1.736(3) . ?
C13A O14 1.200(5) . ?
C13A N15 1.367(5) . ?
C13A C14A 1.496(6) . ?
C13B O24 1.217(4) . ?
C13B N25 1.374(4) . ?
C13B C14B 1.484(5) . ?
C13C O34 1.208(4) . ?
C13C N35 1.372(5) . ?
C13C C14C 1.492(5) . ?
C13D O44 1.205(5) . ?
C13D N45 1.361(5) . ?
C13D C14D 1.487(6) . ?
C14A H44 0.9600 . ?
C14A H45 0.9600 . ?
C14A H55 0.9600 . ?
C14B H1 0.9600 . ?
C14B H3 0.9600 . ?
C14B H4 0.9600 . ?
C14C H30 0.9600 . ?
C14C H31 0.9600 . ?
C14C H42 0.9600 . ?
C14D H16 0.9600 . ?
C14D H17 0.9600 . ?
C14D H18 0.9600 . ?
N11 O11 1.220(5) . ?
N11 O12 1.225(6) . ?
N12 H51 0.8600 . ?
N13 N14 1.401(4) . ?
N21 O22 1.216(4) . ?
N21 O21 1.225(4) . ?
N22 H7 0.8600 . ?
N23 N24 1.396(4) . ?
N25 H14 0.8600 . ?
N31 O31 1.217(4) . ?
N31 O32 1.223(4) . ?
N32 H35 0.8600 . ?
N33 N34 1.393(4) . ?
N35 H41 0.8600 . ?
N41 O41 1.225(5) . ?
N41 O42 1.236(5) . ?
N42 H22 0.8600 . ?
N43 N44 1.393(4) . ?
N45 H28 0.8600 . ?

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
C2A C1A C6A 122.4(4) . . ?
C2A C1A N11 116.0(4) . . ?
C6A C1A N11 121.6(4) . . ?
C2B C1B C6B 123.3(3) . . ?
C2B C1B N21 115.9(3) . . ?
C6B C1B N21 120.6(3) . . ?
C2C C1C C6C 122.7(3) . . ?
C2C C1C N31 115.9(3) . . ?
C6C C1C N31 121.4(3) . . ?
C2D C1D C6D 122.9(3) . . ?
C2D C1D N41 115.7(4) . . ?
C6D C1D N41 121.3(4) . . ?
C3A C2A C1A 119.5(3) . . ?
C3A C2A H46 120.3 . . ?
C1A C2A H46 120.3 . . ?
C3B C2B C1B 119.2(3) . . ?
C3B C2B H9 120.4 . . ?
C1B C2B H9 120.4 . . ?
C3C C2C C1C 119.6(3) . . ?
C3C C2C H29 120.2 . . ?
C1C C2C H29 120.2 . . ?
C3D C2D C1D 119.0(3) . . ?
C3D C2D H21 120.5 . . ?
C1D C2D H21 120.5 . . ?
C2A C3A C4A 120.2(3) . . ?
C2A C3A Cl1 120.4(3) . . ?
C4A C3A Cl1 119.4(3) . . ?
C2B C3B C4B 120.3(3) . . ?
C2B C3B Cl2 120.7(3) . . ?
C4B C3B Cl2 118.9(3) . . ?
C2C C3C C4C 120.3(3) . . ?
C2C C3C Cl3 120.1(3) . . ?
C4C C3C Cl3 119.6(3) . . ?
C2D C3D C4D 120.3(3) . . ?
C2D C3D Cl4 121.2(3) . . ?
C4D C3D Cl4 118.4(3) . . ?
C5A C4A C3A 121.2(3) . . ?
C5A C4A H47 119.4 . . ?
C3A C4A H47 119.4 . . ?
C5B C4B C3B 121.3(3) . . ?
C5B C4B H10 119.3 . . ?
C3B C4B H10 119.3 . . ?
C5C C4C C3C 121.2(3) . . ?
C5C C4C H34 119.4 . . ?
C3C C4C H34 119.4 . . ?
C5D C4D C3D 121.3(3) . . ?
C5D C4D H20 119.3 . . ?
C3D C4D H20 119.3 . . ?
C4A C5A C6A 120.8(3) . . ?
C4A C5A C7A 120.7(3) . . ?
C6A C5A C7A 118.4(3) . . ?
C4B C5B C6B 120.9(3) . . ?
C4B C5B C9B 119.1(3) . . ?
C6B C5B C9B 119.9(3) . . ?
C4C C5C C6C 120.9(3) . . ?
C4C C5C C9C 120.4(3) . . ?
C6C C5C C9C 118.7(3) . . ?
C4D C5D C6D 120.8(3) . . ?
C4D C5D C7D 120.2(3) . . ?
C6D C5D C7D 118.9(3) . . ?
N12 C6A C1A 123.8(3) . . ?
N12 C6A C5A 120.3(3) . . ?
C1A C6A C5A 115.9(3) . . ?
C7B C6B C5B 120.0(3) . . ?
C7B C6B C1B 125.1(3) . . ?
C5B C6B C1B 114.9(3) . . ?
N32 C6C C1C 124.2(3) . . ?
N32 C6C C5C 120.6(3) . . ?
C1C C6C C5C 115.1(3) . . ?
N42 C6D C1D 124.4(3) . . ?
N42 C6D C5D 120.1(3) . . ?
C1D C6D C5D 115.5(3) . . ?
N13 C7A C5A 112.6(3) . . ?
N13 C7A C8A 112.8(3) . . ?
C5A C7A C8A 111.2(3) . . ?
N13 C7A S1 102.2(2) . . ?
C5A C7A S1 108.7(2) . . ?
C8A C7A S1 108.8(2) . . ?
C6B C7B N22 122.8(3) . . ?
C6B C7B H8 118.6 . . ?
N22 C7B H8 118.6 . . ?
N32 C7C C8C 109.5(3) . . ?
N32 C7C H36 109.8 . . ?
C8C C7C H36 109.8 . . ?
N32 C7C H37 109.8 . . ?
C8C C7C H37 109.8 . . ?
H36 C7C H37 108.2 . . ?
N43 C7D C5D 111.6(3) . . ?
N43 C7D C8D 113.1(3) . . ?
C5D C7D C8D 110.3(3) . . ?
N43 C7D S4 102.7(2) . . ?
C5D C7D S4 109.5(2) . . ?
C8D C7D S4 109.3(2) . . ?
C9A C8A C7A 109.2(3) . . ?
C9A C8A H49 109.8 . . ?
C7A C8A H49 109.8 . . ?
C9A C8A H50 109.8 . . ?
C7A C8A H50 109.8 . . ?
H49 C8A H50 108.3 . . ?
N22 C8B C9B 109.6(3) . . ?
N22 C8B H5 109.7 . . ?
C9B C8B H5 109.7 . . ?
N22 C8B H6 109.7 . . ?
C9B C8B H6 109.7 . . ?
H5 C8B H6 108.2 . . ?
C7C C8C C9C 109.5(3) . . ?
C7C C8C H32 109.8 . . ?
C9C C8C H32 109.8 . . ?
C7C C8C H33 109.8 . . ?
C9C C8C H33 109.8 . . ?
H32 C8C H33 108.2 . . ?
C9D C8D C7D 109.6(3) . . ?
C9D C8D H23 109.7 . . ?
C7D C8D H23 109.7 . . ?
C9D C8D H24 109.7 . . ?
C7D C8D H24 109.7 . . ?
H23 C8D H24 108.2 . . ?
N12 C9A C8A 110.4(3) . . ?
N12 C9A H48 124.8 . . ?
C8A C9A H48 124.8 . . ?
N23 C9B C5B 111.0(3) . . ?
N23 C9B C8B 113.6(3) . . ?
C5B C9B C8B 111.5(3) . . ?
N23 C9B S2 102.9(2) . . ?
C5B C9B S2 108.6(2) . . ?
C8B C9B S2 108.7(2) . . ?
N33 C9C C8C 112.6(3) . . ?
N33 C9C C5C 111.0(2) . . ?
C8C C9C C5C 111.1(3) . . ?
N33 C9C S3 102.9(2) . . ?
C8C C9C S3 108.5(2) . . ?
C5C C9C S3 110.4(2) . . ?
N42 C9D C8D 110.0(3) . . ?
N42 C9D H19 125.0 . . ?
C8D C9D H19 125.0 . . ?
O13 C10A N13 120.1(3) . . ?
O13 C10A C11A 123.3(3) . . ?
N13 C10A C11A 116.6(3) . . ?
O23 C10B N23 120.2(3) . . ?
O23 C10B C11B 121.6(3) . . ?
N23 C10B C11B 118.3(3) . . ?
O33 C10C N33 119.9(3) . . ?
O33 C10C C11C 121.7(3) . . ?
N33 C10C C11C 118.4(3) . . ?
O43 C10D N43 120.6(3) . . ?
O43 C10D C11D 122.4(3) . . ?
N43 C10D C11D 117.0(3) . . ?
C10A C11A H52 109.5 . . ?
C10A C11A H53 109.5 . . ?
H52 C11A H53 109.5 . . ?
C10A C11A H54 109.5 . . ?
H52 C11A H54 109.5 . . ?
H53 C11A H54 109.5 . . ?
C10B C11B H11 109.5 . . ?
C10B C11B H12 109.5 . . ?
H11 C11B H12 109.5 . . ?
C10B C11B H13 109.5 . . ?
H11 C11B H13 109.5 . . ?
H12 C11B H13 109.5 . . ?
C10C C11C H38 109.5 . . ?
C10C C11C H39 109.5 . . ?
H38 C11C H39 109.5 . . ?
C10C C11C H40 109.5 . . ?
H38 C11C H40 109.5 . . ?
H39 C11C H40 109.5 . . ?
C10D C11D H25 109.5 . . ?
C10D C11D H26 109.5 . . ?
H25 C11D H26 109.5 . . ?
C10D C11D H27 109.5 . . ?
H25 C11D H27 109.5 . . ?
H26 C11D H27 109.5 . . ?
N14 C12A N15 118.8(3) . . ?
N14 C12A S1 119.3(3) . . ?
N15 C12A S1 121.8(2) . . ?
N24 C12B N25 119.7(3) . . ?
N24 C12B S2 118.9(2) . . ?
N25 C12B S2 121.4(2) . . ?
N34 C12C N35 120.3(3) . . ?
N34 C12C S3 118.7(2) . . ?
N35 C12C S3 121.1(2) . . ?
N44 C12D N45 119.4(3) . . ?
N44 C12D S4 119.6(3) . . ?
N45 C12D S4 121.0(3) . . ?
O14 C13A N15 122.1(4) . . ?
O14 C13A C14A 123.4(4) . . ?
N15 C13A C14A 114.4(3) . . ?
O24 C13B N25 120.6(3) . . ?
O24 C13B C14B 123.1(3) . . ?
N25 C13B C14B 116.3(3) . . ?
O34 C13C N35 120.9(3) . . ?
O34 C13C C14C 123.5(4) . . ?
N35 C13C C14C 115.6(3) . . ?
O44 C13D N45 121.3(4) . . ?
O44 C13D C14D 122.4(4) . . ?
N45 C13D C14D 116.3(4) . . ?
C13A C14A H44 109.5 . . ?
C13A C14A H45 109.5 . . ?
H44 C14A H45 109.5 . . ?
C13A C14A H55 109.5 . . ?
H44 C14A H55 109.5 . . ?
H45 C14A H55 109.5 . . ?
C13B C14B H1 109.5 . . ?
C13B C14B H3 109.5 . . ?
H1 C14B H3 109.5 . . ?
C13B C14B H4 109.5 . . ?
H1 C14B H4 109.5 . . ?
H3 C14B H4 109.5 . . ?
C13C C14C H30 109.5 . . ?
C13C C14C H31 109.5 . . ?
H30 C14C H31 109.5 . . ?
C13C C14C H42 109.5 . . ?
H30 C14C H42 109.5 . . ?
H31 C14C H42 109.5 . . ?
C13D C14D H16 109.5 . . ?
C13D C14D H17 109.5 . . ?
H16 C14D H17 109.5 . . ?
C13D C14D H18 109.5 . . ?
H16 C14D H18 109.5 . . ?
H17 C14D H18 109.5 . . ?
O11 N11 O12 121.4(4) . . ?
O11 N11 C1A 118.9(5) . . ?
O12 N11 C1A 119.7(4) . . ?
C6A N12 C9A 123.5(3) . . ?
C6A N12 H51 118.2 . . ?
C9A N12 H51 118.2 . . ?
C10A N13 N14 118.7(3) . . ?
C10A N13 C7A 123.1(3) . . ?
N14 N13 C7A 118.0(3) . . ?
C12A N14 N13 110.1(3) . . ?
C13A N15 C12A 123.8(3) . . ?
O22 N21 O21 121.6(3) . . ?
O22 N21 C1B 118.7(4) . . ?
O21 N21 C1B 119.7(3) . . ?
C7B N22 C8B 110.2(3) . . ?
C7B N22 H7 124.9 . . ?
C8B N22 H7 124.9 . . ?
C10B N23 N24 119.1(3) . . ?
C10B N23 C9B 122.9(3) . . ?
N24 N23 C9B 117.1(2) . . ?
C12B N24 N23 110.8(3) . . ?
C13B N25 C12B 124.1(3) . . ?
C13B N25 H14 118.0 . . ?
C12B N25 H14 118.0 . . ?
O31 N31 O32 121.7(3) . . ?
O31 N31 C1C 119.1(3) . . ?
O32 N31 C1C 119.2(3) . . ?
C6C N32 C7C 122.2(3) . . ?
C6C N32 H35 118.9 . . ?
C7C N32 H35 118.9 . . ?
C10C N33 N34 119.9(3) . . ?
C10C N33 C9C 122.3(3) . . ?
N34 N33 C9C 117.3(2) . . ?
C12C N34 N33 111.3(3) . . ?
C13C N35 C12C 125.3(3) . . ?
C13C N35 H41 117.4 . . ?
C12C N35 H41 117.4 . . ?
O41 N41 O42 122.3(4) . . ?
O41 N41 C1D 118.8(4) . . ?
O42 N41 C1D 118.9(4) . . ?
C6D N42 C9D 123.5(3) . . ?
C6D N42 H22 118.2 . . ?
C9D N42 H22 118.2 . . ?
C10D N43 N44 117.9(3) . . ?
C10D N43 C7D 123.5(3) . . ?
N44 N43 C7D 117.6(2) . . ?
C12D N44 N43 110.4(3) . . ?
C13D N45 C12D 125.2(3) . . ?
C13D N45 H28 117.4 . . ?
C12D N45 H28 117.4 . . ?
C12A S1 C7A 89.84(16) . . ?
C12B S2 C9B 89.44(15) . . ?
C12C S3 C9C 89.26(15) . . ?
C12D S4 C7D 89.39(15) . . ?

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
C6A C1A C2A C3A 0.1(6) . . . . ?
N11 C1A C2A C3A -178.9(4) . . . . ?
C6B C1B C2B C3B 1.0(5) . . . . ?
N21 C1B C2B C3B -174.9(3) . . . . ?
C6C C1C C2C C3C -2.0(5) . . . . ?
N31 C1C C2C C3C 176.3(3) . . . . ?
C6D C1D C2D C3D -0.6(6) . . . . ?
N41 C1D C2D C3D -177.4(3) . . . . ?
C1A C2A C3A C4A -0.6(6) . . . . ?
C1A C2A C3A Cl1 179.8(3) . . . . ?
C1B C2B C3B C4B -1.0(5) . . . . ?
C1B C2B C3B Cl2 177.7(3) . . . . ?
C1C C2C C3C C4C 1.8(6) . . . . ?
C1C C2C C3C Cl3 -177.2(3) . . . . ?
C1D C2D C3D C4D 2.6(5) . . . . ?
C1D C2D C3D Cl4 179.0(3) . . . . ?
C2A C3A C4A C5A -0.2(5) . . . . ?
Cl1 C3A C4A C5A 179.4(3) . . . . ?
C2B C3B C4B C5B -0.1(5) . . . . ?
Cl2 C3B C4B C5B -178.8(3) . . . . ?
C2C C3C C4C C5C 0.7(6) . . . . ?
Cl3 C3C C4C C5C 179.8(3) . . . . ?
C2D C3D C4D C5D -0.6(5) . . . . ?
Cl4 C3D C4D C5D -177.2(3) . . . . ?
C3A C4A C5A C6A 1.6(5) . . . . ?
C3A C4A C5A C7A 178.1(3) . . . . ?
C3B C4B C5B C6B 1.2(5) . . . . ?
C3B C4B C5B C9B 178.2(3) . . . . ?
C3C C4C C5C C6C -3.2(5) . . . . ?
C3C C4C C5C C9C 176.9(3) . . . . ?
C3D C4D C5D C6D -3.4(5) . . . . ?
C3D C4D C5D C7D 178.0(3) . . . . ?
C2A C1A C6A N12 -179.4(4) . . . . ?
N11 C1A C6A N12 -0.4(6) . . . . ?
C2A C1A C6A C5A 1.1(6) . . . . ?
N11 C1A C6A C5A -179.9(4) . . . . ?
C4A C5A C6A N12 178.5(3) . . . . ?
C7A C5A C6A N12 1.9(5) . . . . ?
C4A C5A C6A C1A -2.0(5) . . . . ?
C7A C5A C6A C1A -178.6(3) . . . . ?
C4B C5B C6B C7B 178.3(3) . . . . ?
C9B C5B C6B C7B 1.3(5) . . . . ?
C4B C5B C6B C1B -1.1(5) . . . . ?
C9B C5B C6B C1B -178.0(3) . . . . ?
C2B C1B C6B C7B -179.3(4) . . . . ?
N21 C1B C6B C7B -3.6(6) . . . . ?
C2B C1B C6B C5B 0.0(5) . . . . ?
N21 C1B C6B C5B 175.7(3) . . . . ?
C2C C1C C6C N32 179.3(3) . . . . ?
N31 C1C C6C N32 1.1(5) . . . . ?
C2C C1C C6C C5C -0.4(5) . . . . ?
N31 C1C C6C C5C -178.6(3) . . . . ?
C4C C5C C6C N32 -176.8(3) . . . . ?
C9C C5C C6C N32 3.2(4) . . . . ?
C4C C5C C6C C1C 2.9(4) . . . . ?
C9C C5C C6C C1C -177.1(3) . . . . ?
C2D C1D C6D N42 178.1(3) . . . . ?
N41 C1D C6D N42 -5.3(5) . . . . ?
C2D C1D C6D C5D -3.1(5) . . . . ?
N41 C1D C6D C5D 173.5(3) . . . . ?
C4D C5D C6D N42 -176.1(3) . . . . ?
C7D C5D C6D N42 2.5(5) . . . . ?
C4D C5D C6D C1D 5.0(5) . . . . ?
C7D C5D C6D C1D -176.4(3) . . . . ?
C4A C5A C7A N13 27.4(4) . . . . ?
C6A C5A C7A N13 -156.0(3) . . . . ?
C4A C5A C7A C8A 155.1(3) . . . . ?
C6A C5A C7A C8A -28.3(4) . . . . ?
C4A C5A C7A S1 -85.1(3) . . . . ?
C6A C5A C7A S1 91.5(3) . . . . ?
C5B C6B C7B N22 -10.9(5) . . . . ?
C1B C6B C7B N22 168.4(4) . . . . ?
C4D C5D C7D N43 -29.3(4) . . . . ?
C6D C5D C7D N43 152.0(3) . . . . ?
C4D C5D C7D C8D -156.0(3) . . . . ?
C6D C5D C7D C8D 25.4(4) . . . . ?
C4D C5D C7D S4 83.7(3) . . . . ?
C6D C5D C7D S4 -94.9(3) . . . . ?
N13 C7A C8A C9A -177.8(3) . . . . ?
C5A C7A C8A C9A 54.5(4) . . . . ?
S1 C7A C8A C9A -65.2(3) . . . . ?
N32 C7C C8C C9C 60.1(3) . . . . ?
N43 C7D C8D C9D 179.7(3) . . . . ?
C5D C7D C8D C9D -54.5(4) . . . . ?
S4 C7D C8D C9D 66.0(3) . . . . ?
C7A C8A C9A N12 -55.4(4) . . . . ?
C4B C5B C9B N23 33.8(4) . . . . ?
C6B C5B C9B N23 -149.1(3) . . . . ?
C4B C5B C9B C8B 161.6(3) . . . . ?
C6B C5B C9B C8B -21.4(4) . . . . ?
C4B C5B C9B S2 -78.6(3) . . . . ?
C6B C5B C9B S2 98.4(3) . . . . ?
N22 C8B C9B N23 174.8(3) . . . . ?
N22 C8B C9B C5B 48.5(4) . . . . ?
N22 C8B C9B S2 -71.2(3) . . . . ?
C7C C8C C9C N33 -175.8(3) . . . . ?
C7C C8C C9C C5C -50.6(3) . . . . ?
C7C C8C C9C S3 70.9(3) . . . . ?
C4C C5C C9C N33 -34.3(4) . . . . ?
C6C C5C C9C N33 145.8(3) . . . . ?
C4C C5C C9C C8C -160.4(3) . . . . ?
C6C C5C C9C C8C 19.7(4) . . . . ?
C4C C5C C9C S3 79.2(3) . . . . ?
C6C C5C C9C S3 -100.8(3) . . . . ?
C7D C8D C9D N42 56.8(4) . . . . ?
C2A C1A N11 O11 -1.5(7) . . . . ?
C6A C1A N11 O11 179.5(5) . . . . ?
C2A C1A N11 O12 179.3(5) . . . . ?
C6A C1A N11 O12 0.3(8) . . . . ?
C1A C6A N12 C9A 177.2(4) . . . . ?
C5A C6A N12 C9A -3.4(6) . . . . ?
C8A C9A N12 C6A 31.0(5) . . . . ?
O13 C10A N13 N14 175.3(3) . . . . ?
C11A C10A N13 N14 -5.1(5) . . . . ?
O13 C10A N13 C7A -0.1(5) . . . . ?
C11A C10A N13 C7A 179.4(3) . . . . ?
C5A C7A N13 C10A 66.4(4) . . . . ?
C8A C7A N13 C10A -60.4(4) . . . . ?
S1 C7A N13 C10A -177.1(3) . . . . ?
C5A C7A N13 N14 -109.0(3) . . . . ?
C8A C7A N13 N14 124.1(3) . . . . ?
S1 C7A N13 N14 7.4(3) . . . . ?
N15 C12A N14 N13 178.8(3) . . . . ?
S1 C12A N14 N13 0.0(4) . . . . ?
C10A N13 N14 C12A 179.0(3) . . . . ?
C7A N13 N14 C12A -5.3(4) . . . . ?
O14 C13A N15 C12A -1.5(6) . . . . ?
C14A C13A N15 C12A 178.1(4) . . . . ?
N14 C12A N15 C13A 178.1(3) . . . . ?
S1 C12A N15 C13A -3.1(5) . . . . ?
C2B C1B N21 O22 2.3(6) . . . . ?
C6B C1B N21 O22 -173.7(4) . . . . ?
C2B C1B N21 O21 -178.8(4) . . . . ?
C6B C1B N21 O21 5.2(6) . . . . ?
C6B C7B N22 C8B 39.6(5) . . . . ?
C9B C8B N22 C7B -57.1(4) . . . . ?
O23 C10B N23 N24 -179.2(3) . . . . ?
C11B C10B N23 N24 1.1(4) . . . . ?
O23 C10B N23 C9B 12.0(5) . . . . ?
C11B C10B N23 C9B -167.7(3) . . . . ?
C5B C9B N23 C10B 63.0(4) . . . . ?
C8B C9B N23 C10B -63.6(4) . . . . ?
S2 C9B N23 C10B 179.0(2) . . . . ?
C5B C9B N23 N24 -106.0(3) . . . . ?
C8B C9B N23 N24 127.4(3) . . . . ?
S2 C9B N23 N24 10.0(3) . . . . ?
N25 C12B N24 N23 -179.4(2) . . . . ?
S2 C12B N24 N23 1.2(3) . . . . ?
C10B N23 N24 C12B -177.3(3) . . . . ?
C9B N23 N24 C12B -7.9(4) . . . . ?
O24 C13B N25 C12B -0.4(5) . . . . ?
C14B C13B N25 C12B 179.3(3) . . . . ?
N24 C12B N25 C13B 177.4(3) . . . . ?
S2 C12B N25 C13B -3.2(4) . . . . ?
C2C C1C N31 O31 0.0(5) . . . . ?
C6C C1C N31 O31 178.3(3) . . . . ?
C2C C1C N31 O32 -177.8(3) . . . . ?
C6C C1C N31 O32 0.5(5) . . . . ?
C1C C6C N32 C7C -172.6(3) . . . . ?
C5C C6C N32 C7C 7.1(5) . . . . ?
C8C C7C N32 C6C -39.4(4) . . . . ?
O33 C10C N33 N34 171.9(3) . . . . ?
C11C C10C N33 N34 -8.8(4) . . . . ?
O33 C10C N33 C9C -0.8(5) . . . . ?
C11C C10C N33 C9C 178.6(3) . . . . ?
C8C C9C N33 C10C 64.0(4) . . . . ?
C5C C9C N33 C10C -61.3(4) . . . . ?
S3 C9C N33 C10C -179.3(2) . . . . ?
C8C C9C N33 N34 -108.8(3) . . . . ?
C5C C9C N33 N34 125.9(3) . . . . ?
S3 C9C N33 N34 7.9(3) . . . . ?
N35 C12C N34 N33 179.1(3) . . . . ?
S3 C12C N34 N33 -0.8(4) . . . . ?
C10C N33 N34 C12C -178.1(3) . . . . ?
C9C N33 N34 C12C -5.2(4) . . . . ?
O34 C13C N35 C12C -4.8(6) . . . . ?
C14C C13C N35 C12C 175.2(3) . . . . ?
N34 C12C N35 C13C -171.9(3) . . . . ?
S3 C12C N35 C13C 8.0(5) . . . . ?
C2D C1D N41 O41 11.6(5) . . . . ?
C6D C1D N41 O41 -165.1(4) . . . . ?
C2D C1D N41 O42 -169.6(4) . . . . ?
C6D C1D N41 O42 13.6(6) . . . . ?
C1D C6D N42 C9D 178.7(3) . . . . ?
C5D C6D N42 C9D -0.1(5) . . . . ?
C8D C9D N42 C6D -30.3(5) . . . . ?
O43 C10D N43 N44 -177.9(3) . . . . ?
C11D C10D N43 N44 0.4(4) . . . . ?
O43 C10D N43 C7D -10.1(5) . . . . ?
C11D C10D N43 C7D 168.2(3) . . . . ?
C5D C7D N43 C10D -56.2(4) . . . . ?
C8D C7D N43 C10D 68.9(4) . . . . ?
S4 C7D N43 C10D -173.4(2) . . . . ?
C5D C7D N43 N44 111.7(3) . . . . ?
C8D C7D N43 N44 -123.2(3) . . . . ?
S4 C7D N43 N44 -5.6(3) . . . . ?
N45 C12D N44 N43 -178.3(3) . . . . ?
S4 C12D N44 N43 0.4(4) . . . . ?
C10D N43 N44 C12D 172.3(3) . . . . ?
C7D N43 N44 C12D 3.8(4) . . . . ?
O44 C13D N45 C12D 2.0(7) . . . . ?
C14D C13D N45 C12D -177.7(4) . . . . ?
N44 C12D N45 C13D -178.7(4) . . . . ?
S4 C12D N45 C13D 2.6(6) . . . . ?
N14 C12A S1 C7A 3.8(3) . . . . ?
N15 C12A S1 C7A -175.0(3) . . . . ?
N13 C7A S1 C12A -5.7(2) . . . . ?
C5A C7A S1 C12A 113.6(2) . . . . ?
C8A C7A S1 C12A -125.1(2) . . . . ?
N24 C12B S2 C9B 4.0(3) . . . . ?
N25 C12B S2 C9B -175.4(3) . . . . ?
N23 C9B S2 C12B -7.2(2) . . . . ?
C5B C9B S2 C12B 110.5(2) . . . . ?
C8B C9B S2 C12B -128.0(2) . . . . ?
N34 C12C S3 C9C 4.7(3) . . . . ?
N35 C12C S3 C9C -175.2(3) . . . . ?
N33 C9C S3 C12C -6.4(2) . . . . ?
C8C C9C S3 C12C 113.1(2) . . . . ?
C5C C9C S3 C12C -124.8(2) . . . . ?
N44 C12D S4 C7D -3.2(3) . . . . ?
N45 C12D S4 C7D 175.5(3) . . . . ?
N43 C7D S4 C12D 4.4(2) . . . . ?
C5D C7D S4 C12D -114.3(2) . . . . ?
C8D C7D S4 C12D 124.7(2) . . . . ?

_refine_diff_density_max         1.112
_refine_diff_density_min         -0.402
_refine_diff_density_rms         0.070

_shelxl_version_number           2014-3

