# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_273K
_database_code_depnum_ccdc_archive 'CCDC 1432879'
_audit_update_record             
;
2016-03-17 deposited with the CCDC.
2016-11-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H12 N4 S4, 8(C H4 N2 S), 4(Cl), 4(C H)'
_chemical_formula_sum            'C20 H48 Cl4 N20 S12'
_chemical_formula_weight         1095.30

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      orthorhombic
_space_group_IT_number           63
_space_group_name_H-M_alt        'C m c m'
_space_group_name_Hall           '-C 2c 2'

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

_cell_length_a                   14.430(9)
_cell_length_b                   10.330(9)
_cell_length_c                   8.417(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1254.6(17)
_cell_formula_units_Z            1
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    1767
_cell_measurement_theta_min      3.4254
_cell_measurement_theta_max      27.4198

_exptl_crystal_description       needlelike
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.450
_exptl_crystal_F_000             568
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2000
_exptl_crystal_size_mid          0.2000
_exptl_crystal_size_min          0.2000
_exptl_absorpt_coefficient_mu    0.777
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?

_exptl_absorpt_correction_T_min  0.9300
_exptl_absorpt_correction_T_max  1.0000

_exptl_absorpt_correction_type   Multi-scan

_exptl_absorpt_process_details   
;   Higashi, T.(1995). Program for Absorption Correction.
    Rigaku Corporation, Tokyo, Japan. 
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?

_diffrn_measurement_device_type  'Saturn724+ (4x4 bin mode)'
_diffrn_measurement_method       CCD_Profile_fitting
_diffrn_detector_area_resol_mean 28.5714

_diffrn_reflns_number            4412
_diffrn_reflns_av_unetI/netI     0.0219
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.427
_diffrn_reflns_theta_max         27.415
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             794
_reflns_number_gt                682
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1094P)²+3.0346P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         794
_refine_ls_number_parameters     60
_refine_ls_number_restraints     62
_refine_ls_R_factor_all          0.0728
_refine_ls_R_factor_gt           0.0644
_refine_ls_wR_factor_ref         0.1945
_refine_ls_wR_factor_gt          0.1861
_refine_ls_goodness_of_fit_ref   1.128
_refine_ls_restrained_S_all      1.154
_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 0.3157(3) 0.6740(4) 0.2500 0.0347(10) Uani 1 2 d S T P . .
C3 C 0.0000 0.3963(11) -0.013(2) 0.080(4) Uani 0.5 2 d DGS TU P . .
H4A H 0.0000 0.3140 -0.0473 0.096 Uiso 0.5 2 d R U P . .
S2 S -0.0890(4) 0.4785(10) -0.011(2) 0.105(3) Uani 0.25 1 d G U P . .
C4 C -0.0590(13) 0.6050(10) 0.056(2) 0.097(7) Uani 0.25 1 d G U P . .
H5A H -0.0938 0.6699 0.0725 0.116 Uiso 0.25 1 d R U P . .
C2 C 0.0426(16) 0.5985(13) 0.089(2) 0.085(6) Uani 0.25 1 d DG U P . .
H3A H 0.0760 0.6581 0.1281 0.101 Uiso 0.25 1 d R U P . .
N2 N 0.0722(9) 0.4745(18) 0.042(3) 0.097(6) Uani 0.25 1 d DG U P . .
H2C H 0.1285 0.4495 0.0476 0.116 Uiso 0.25 1 d R U P . .
Cl1 Cl 0.0000 0.91294(14) 0.2500 0.0408(5) Uani 1 4 d S T P . .
N1 N 0.3523(2) 0.6318(3) 0.1154(3) 0.0459(8) Uani 1 1 d . . . . .
H1A H 0.3983 0.5788 0.1175 0.055 Uiso 1 1 calc R U . . .
H1B H 0.3301 0.6573 0.0259 0.055 Uiso 1 1 calc R U . . .
S1 S 0.22392(11) 0.77816(15) 0.2500 0.0580(6) Uani 1 2 d S T P . .


_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 N1 1.323(3) . ?
C1 N1 1.324(3) 10_556 ?
C1 S1 1.707(5) . ?
C3 C2 0.89(3) 9_565 ?
C3 C2 0.89(3) 4_565 ?
C3 C4 0.925(16) 4_565 ?
C3 C4 0.925(18) 9_565 ?
C3 N2 1.398(13) 12 ?
C3 N2 1.398(7) . ?
C3 S2 1.540(8) . ?
C3 S2 1.540(16) 12 ?
C3 N2 1.71(3) 4_565 ?
C3 N2 1.711(15) 9_565 ?
C3 S2 1.834(12) 9_565 ?
C3 S2 1.834(13) 4_565 ?
S2 S2 0.48(2) 4_565 ?
S2 N2 0.515(8) 12 ?
S2 N2 0.60(3) 9_565 ?
S2 C4 1.036(17) 4_565 ?
S2 C2 1.23(2) 9_565 ?
S2 C4 1.488(8) . ?
S2 C2 1.641(14) 12 ?
S2 C3 1.834(13) 9_565 ?
S2 C2 2.161(13) 4_565 ?
C4 C2 0.37(2) 12 ?
C4 C3 0.93(2) 9_565 ?
C4 S2 1.04(2) 4_565 ?
C4 N2 1.18(3) 9_565 ?
C4 N2 1.366(7) 12 ?
C4 C2 1.495(8) . ?
C4 C4 1.70(4) 12 ?
C2 C4 0.37(3) 12 ?
C2 C3 0.89(2) 9_565 ?
C2 S2 1.23(4) 9_565 ?
C2 C2 1.23(4) 12 ?
C2 N2 1.40(4) 4_565 ?
C2 N2 1.405(7) . ?
C2 S2 1.641(5) 12 ?
C2 S2 2.161(17) 4_565 ?
N2 S2 0.515(11) 12 ?
N2 S2 0.60(3) 9_565 ?
N2 N2 0.89(4) 4_565 ?
N2 C4 1.18(4) 9_565 ?
N2 C4 1.366(13) 12 ?
N2 C2 1.40(3) 4_565 ?
N2 C3 1.71(3) 9_565 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 N1 117.7(4) . 10_556 ?
N1 C1 S1 121.2(2) . . ?
N1 C1 S1 121.2(2) 10_556 . ?
C2 C3 C2 88(4) 9_565 4_565 ?
C2 C3 C4 23.5(6) 9_565 4_565 ?
C2 C3 C4 111(4) 4_565 4_565 ?
C2 C3 C4 111(4) 9_565 9_565 ?
C2 C3 C4 23.5(10) 4_565 9_565 ?
C4 C3 C4 134(4) 4_565 9_565 ?
C2 C3 N2 71.9(17) 9_565 12 ?
C2 C3 N2 136(2) 4_565 12 ?
C4 C3 N2 56.8(17) 4_565 12 ?
C4 C3 N2 146(2) 9_565 12 ?
C2 C3 N2 136.1(19) 9_565 . ?
C2 C3 N2 72(2) 4_565 . ?
C4 C3 N2 145.6(12) 4_565 . ?
C4 C3 N2 57(3) 9_565 . ?
N2 C3 N2 96.3(4) 12 . ?
C2 C3 S2 52.9(17) 9_565 . ?
C2 C3 S2 123(2) 4_565 . ?
C4 C3 S2 40.9(14) 4_565 . ?
C4 C3 S2 141(2) 9_565 . ?
N2 C3 S2 19.4(3) 12 . ?
N2 C3 S2 107.5 . . ?
C2 C3 S2 123(2) 9_565 12 ?
C2 C3 S2 52.8(19) 4_565 12 ?
C4 C3 S2 141.3(18) 4_565 12 ?
C4 C3 S2 41(2) 9_565 12 ?
N2 C3 S2 107.5(6) 12 12 ?
N2 C3 S2 19.40(13) . 12 ?
S2 C3 S2 113.1(6) . 12 ?
C2 C3 N2 106(2) 9_565 4_565 ?
C2 C3 N2 55.0(16) 4_565 4_565 ?
C4 C3 N2 121(2) 4_565 4_565 ?
C4 C3 N2 52.7(17) 9_565 4_565 ?
N2 C3 N2 93.0(6) 12 4_565 ?
N2 C3 N2 31.2(13) . 4_565 ?
S2 C3 N2 94.5(6) . 4_565 ?
S2 C3 N2 20.5(7) 12 4_565 ?
C2 C3 N2 55.0(10) 9_565 9_565 ?
C2 C3 N2 106(2) 4_565 9_565 ?
C4 C3 N2 52.7(10) 4_565 9_565 ?
C4 C3 N2 121(2) 9_565 9_565 ?
N2 C3 N2 31.2(13) 12 9_565 ?
N2 C3 N2 93.0(8) . 9_565 ?
S2 C3 N2 20.5(12) . 9_565 ?
S2 C3 N2 94.5(6) 12 9_565 ?
N2 C3 N2 75.0(8) 4_565 9_565 ?
C2 C3 S2 121(2) 9_565 9_565 ?
C2 C3 S2 63.4(13) 4_565 9_565 ?
C4 C3 S2 134(2) 4_565 9_565 ?
C4 C3 S2 53.8(10) 9_565 9_565 ?
N2 C3 S2 94.5(13) 12 9_565 ?
N2 C3 S2 15.0(16) . 9_565 ?
S2 C3 S2 101.2(15) . 9_565 ?
S2 C3 S2 13.1(11) 12 9_565 ?
N2 C3 S2 16.2(7) 4_565 9_565 ?
N2 C3 S2 83.9(10) 9_565 9_565 ?
C2 C3 S2 63.4(9) 9_565 4_565 ?
C2 C3 S2 121(2) 4_565 4_565 ?
C4 C3 S2 53.8(10) 4_565 4_565 ?
C4 C3 S2 134(2) 9_565 4_565 ?
N2 C3 S2 15.0(12) 12 4_565 ?
N2 C3 S2 94.5(5) . 4_565 ?
S2 C3 S2 13.1(6) . 4_565 ?
S2 C3 S2 101.2(4) 12 4_565 ?
N2 C3 S2 83.9(8) 4_565 4_565 ?
N2 C3 S2 16.2(3) 9_565 4_565 ?
S2 C3 S2 88.9(13) 9_565 4_565 ?
S2 S2 N2 74(4) 4_565 12 ?
S2 S2 N2 55(2) 4_565 9_565 ?
N2 S2 N2 105(3) 12 9_565 ?
S2 S2 C4 155.3(4) 4_565 4_565 ?
N2 S2 C4 93(3) 12 4_565 ?
N2 S2 C4 110(3) 9_565 4_565 ?
S2 S2 C2 144(3) 4_565 9_565 ?
N2 S2 C2 99(2) 12 9_565 ?
N2 S2 C2 94(3) 9_565 9_565 ?
C4 S2 C2 16.2(5) 4_565 9_565 ?
S2 S2 C4 16.92(11) 4_565 . ?
N2 S2 C4 66.5(2) 12 . ?
N2 S2 C4 49(3) 9_565 . ?
C4 S2 C4 138.4(5) 4_565 . ?
C2 S2 C4 127.7(9) 9_565 . ?
S2 S2 C3 120.8(11) 4_565 . ?
N2 S2 C3 64.5(13) 12 . ?
N2 S2 C3 96.0(17) 9_565 . ?
C4 S2 C3 35.8(12) 4_565 . ?
C2 S2 C3 35.2(15) 9_565 . ?
C4 S2 C3 104.2 . . ?
S2 S2 C2 26(2) 4_565 12 ?
N2 S2 C2 54.4(7) 12 12 ?
N2 S2 C2 57(3) 9_565 12 ?
C4 S2 C2 130.1(15) 4_565 12 ?
C2 S2 C2 122.7(11) 9_565 12 ?
C4 S2 C2 12.4(7) . 12 ?
C3 S2 C2 94.6(12) . 12 ?
S2 S2 C3 46.2(11) 4_565 9_565 ?
N2 S2 C3 68.3(13) 12 9_565 ?
N2 S2 C3 37(2) 9_565 9_565 ?
C4 S2 C3 109.6(9) 4_565 9_565 ?
C2 S2 C3 97.7(10) 9_565 9_565 ?
C4 S2 C3 30.1(8) . 9_565 ?
C3 S2 C3 78.8(7) . 9_565 ?
C2 S2 C3 29.0(8) 12 9_565 ?
S2 S2 C2 117.2(9) 4_565 4_565 ?
N2 S2 C2 79.7(15) 12 4_565 ?
N2 S2 C2 79.1(13) 9_565 4_565 ?
C4 S2 C2 38.4(8) 4_565 4_565 ?
C2 S2 C2 28.5(4) 9_565 4_565 ?
C4 S2 C2 100.5(8) . 4_565 ?
C3 S2 C2 20.1(11) . 4_565 ?
C2 S2 C2 94.3(8) 12 4_565 ?
C3 S2 C2 71.2(3) 9_565 4_565 ?
C2 C4 C3 73(5) 12 9_565 ?
C2 C4 S2 113(2) 12 4_565 ?
C3 C4 S2 103.3(17) 9_565 4_565 ?
C2 C4 N2 120.0(16) 12 9_565 ?
C3 C4 N2 82(2) 9_565 9_565 ?
S2 C4 N2 25.8(10) 4_565 9_565 ?
C2 C4 N2 88.3(7) 12 12 ?
C3 C4 N2 94.7(13) 9_565 12 ?
S2 C4 N2 24.5(15) 4_565 12 ?
N2 C4 N2 40.0(17) 9_565 12 ?
C2 C4 S2 108.0(6) 12 . ?
C3 C4 S2 96.1(11) 9_565 . ?
S2 C4 S2 7.8(5) 4_565 . ?
N2 C4 S2 22.6(18) 9_565 . ?
N2 C4 S2 20.2(3) 12 . ?
C2 C4 C2 39(5) 12 . ?
C3 C4 C2 33.7(15) 9_565 . ?
S2 C4 C2 116.1(6) 4_565 . ?
N2 C4 C2 104.9(9) 9_565 . ?
N2 C4 C2 96.1(7) 12 . ?
S2 C4 C2 108.4 . . ?
C2 C4 C4 50(5) 12 12 ?
C3 C4 C4 23.0(15) 9_565 12 ?
S2 C4 C4 114.7(5) 4_565 12 ?
N2 C4 C4 99.3(11) 9_565 12 ?
N2 C4 C4 98.0(7) 12 12 ?
S2 C4 C4 106.9 . 12 ?
C2 C4 C4 11.0 . 12 ?
C4 C2 C3 84(5) 12 9_565 ?
C4 C2 S2 51.1(19) 12 9_565 ?
C3 C2 S2 92(2) 9_565 9_565 ?
C4 C2 C2 130(6) 12 12 ?
C3 C2 C2 46.2(17) 9_565 12 ?
S2 C2 C2 123.0(11) 9_565 12 ?
C4 C2 N2 47(2) 12 4_565 ?
C3 C2 N2 71(2) 9_565 4_565 ?
S2 C2 N2 21.2(13) 9_565 4_565 ?
C2 C2 N2 107.7(5) 12 4_565 ?
C4 C2 N2 76.4(12) 12 . ?
C3 C2 N2 93.8(14) 9_565 . ?
S2 C2 N2 25.4(15) 9_565 . ?
C2 C2 N2 107.7 12 . ?
N2 C2 N2 36.9(15) 4_565 . ?
C4 C2 C4 119(6) 12 . ?
C3 C2 C4 35.3(17) 9_565 . ?
S2 C2 C4 117.7(14) 9_565 . ?
C2 C2 C4 11.0 12 . ?
N2 C2 C4 100.2(6) 4_565 . ?
N2 C2 C4 106.7 . . ?
C4 C2 S2 59.6(12) 12 12 ?
C3 C2 S2 87.7(12) 9_565 12 ?
S2 C2 S2 10.1(9) 9_565 12 ?
C2 C2 S2 114.1(9) 12 12 ?
N2 C2 S2 21.1(14) 4_565 12 ?
N2 C2 S2 17.3(3) . 12 ?
C4 C2 S2 109.8(9) . 12 ?
C4 C2 S2 114(5) 12 4_565 ?
C3 C2 S2 36.5(11) 9_565 4_565 ?
S2 C2 S2 94.6(13) 9_565 4_565 ?
C2 C2 S2 28.5(6) 12 4_565 ?
N2 C2 S2 80.3(8) 4_565 4_565 ?
N2 C2 S2 81.2(5) . 4_565 ?
C4 C2 S2 25.5(5) . 4_565 ?
S2 C2 S2 85.7(12) 12 4_565 ?
S2 N2 S2 50(5) 12 9_565 ?
S2 N2 N2 41.0(16) 12 4_565 ?
S2 N2 N2 34(4) 9_565 4_565 ?
S2 N2 C4 61(2) 12 9_565 ?
S2 N2 C4 109(5) 9_565 9_565 ?
N2 N2 C4 81(3) 4_565 9_565 ?
S2 N2 C4 93.3(6) 12 12 ?
S2 N2 C4 45(3) 9_565 12 ?
N2 N2 C4 59(2) 4_565 12 ?
C4 N2 C4 136(2) 9_565 12 ?
S2 N2 C3 96(2) 12 . ?
S2 N2 C3 128(4) 9_565 . ?
N2 N2 C3 94.2(16) 4_565 . ?
C4 N2 C3 41.0(8) 9_565 . ?
C4 N2 C3 119.6(19) 12 . ?
S2 N2 C2 60(2) 12 4_565 ?
S2 N2 C2 102(5) 9_565 4_565 ?
N2 N2 C2 72(3) 4_565 4_565 ?
C4 N2 C2 13.3(9) 9_565 4_565 ?
C4 N2 C2 123.5(19) 12 4_565 ?
C3 N2 C2 37.0(10) . 4_565 ?
S2 N2 C2 108.3(5) 12 . ?
S2 N2 C2 61(5) 9_565 . ?
N2 N2 C2 72(2) 4_565 . ?
C4 N2 C2 141.2(17) 9_565 . ?
C4 N2 C2 15.3(13) 12 . ?
C3 N2 C2 113.1 . . ?
C2 N2 C2 128.0(11) 4_565 . ?
S2 N2 C3 95.5(15) 12 9_565 ?
S2 N2 C3 64(4) 9_565 9_565 ?
N2 N2 C3 54.6(12) 4_565 9_565 ?
C4 N2 C3 110(2) 9_565 9_565 ?
C4 N2 C3 32.6(17) 12 9_565 ?
C3 N2 C3 87.0(5) . 9_565 ?
C2 N2 C3 96.8(14) 4_565 9_565 ?
C2 N2 C3 31.2(7) . 9_565 ?

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
C2 C3 S2 S2 -141(7) 9_565 . . 4_565 ?
C2 C3 S2 S2 -86(5) 4_565 . . 4_565 ?
C4 C3 S2 S2 -169(9) 4_565 . . 4_565 ?
C4 C3 S2 S2 -64(7) 9_565 . . 4_565 ?
N2 C3 S2 S2 51(6) 12 . . 4_565 ?
N2 C3 S2 S2 -6(5) . . . 4_565 ?
S2 C3 S2 S2 -26(5) 12 . . 4_565 ?
N2 C3 S2 S2 -35(6) 4_565 . . 4_565 ?
N2 C3 S2 S2 -53(3) 9_565 . . 4_565 ?
S2 C3 S2 S2 -20(6) 9_565 . . 4_565 ?
C2 C3 S2 N2 168(2) 9_565 . . 12 ?
C2 C3 S2 N2 -136(2) 4_565 . . 12 ?
C4 C3 S2 N2 140(4) 4_565 . . 12 ?
C4 C3 S2 N2 -115(4) 9_565 . . 12 ?
N2 C3 S2 N2 -57.0(11) . . . 12 ?
S2 C3 S2 N2 -76.9(11) 12 . . 12 ?
N2 C3 S2 N2 -86.0(12) 4_565 . . 12 ?
N2 C3 S2 N2 -104(4) 9_565 . . 12 ?
S2 C3 S2 N2 -71.1(13) 9_565 . . 12 ?
S2 C3 S2 N2 -51(6) 4_565 . . 12 ?
C2 C3 S2 N2 -88(4) 9_565 . . 9_565 ?
C2 C3 S2 N2 -33(3) 4_565 . . 9_565 ?
C4 C3 S2 N2 -117(6) 4_565 . . 9_565 ?
C4 C3 S2 N2 -12(5) 9_565 . . 9_565 ?
N2 C3 S2 N2 104(4) 12 . . 9_565 ?
N2 C3 S2 N2 47(3) . . . 9_565 ?
S2 C3 S2 N2 27(3) 12 . . 9_565 ?
N2 C3 S2 N2 18(3) 4_565 . . 9_565 ?
S2 C3 S2 N2 33(3) 9_565 . . 9_565 ?
S2 C3 S2 N2 53(3) 4_565 . . 9_565 ?
C2 C3 S2 C4 28.1(17) 9_565 . . 4_565 ?
C2 C3 S2 C4 84(5) 4_565 . . 4_565 ?
C4 C3 S2 C4 105(7) 9_565 . . 4_565 ?
N2 C3 S2 C4 -140(4) 12 . . 4_565 ?
N2 C3 S2 C4 163(4) . . . 4_565 ?
S2 C3 S2 C4 143(4) 12 . . 4_565 ?
N2 C3 S2 C4 134(4) 4_565 . . 4_565 ?
N2 C3 S2 C4 117(6) 9_565 . . 4_565 ?
S2 C3 S2 C4 149(4) 9_565 . . 4_565 ?
S2 C3 S2 C4 169(9) 4_565 . . 4_565 ?
C2 C3 S2 C2 56(4) 4_565 . . 9_565 ?
C4 C3 S2 C2 -28.1(17) 4_565 . . 9_565 ?
C4 C3 S2 C2 77(5) 9_565 . . 9_565 ?
N2 C3 S2 C2 -168(2) 12 . . 9_565 ?
N2 C3 S2 C2 135(3) . . . 9_565 ?
S2 C3 S2 C2 115(3) 12 . . 9_565 ?
N2 C3 S2 C2 106(3) 4_565 . . 9_565 ?
N2 C3 S2 C2 88(4) 9_565 . . 9_565 ?
S2 C3 S2 C2 121(3) 9_565 . . 9_565 ?
S2 C3 S2 C2 141(7) 4_565 . . 9_565 ?
C2 C3 S2 C4 -137(3) 9_565 . . . ?
C2 C3 S2 C4 -82(3) 4_565 . . . ?
C4 C3 S2 C4 -165(4) 4_565 . . . ?
C4 C3 S2 C4 -61(4) 9_565 . . . ?
N2 C3 S2 C4 54.8(11) 12 . . . ?
N2 C3 S2 C4 -2.2 . . . . ?
S2 C3 S2 C4 -22.1 12 . . . ?
N2 C3 S2 C4 -31.2(15) 4_565 . . . ?
N2 C3 S2 C4 -49(3) 9_565 . . . ?
S2 C3 S2 C4 -16.3(16) 9_565 . . . ?
S2 C3 S2 C4 4(5) 4_565 . . . ?
C2 C3 S2 C2 -145(3) 9_565 . . 12 ?
C2 C3 S2 C2 -90(2) 4_565 . . 12 ?
C4 C3 S2 C2 -174(4) 4_565 . . 12 ?
C4 C3 S2 C2 -69(4) 9_565 . . 12 ?
N2 C3 S2 C2 46.7(8) 12 . . 12 ?
N2 C3 S2 C2 -10.3(4) . . . 12 ?
S2 C3 S2 C2 -30.1(4) 12 . . 12 ?
N2 C3 S2 C2 -39.3(13) 4_565 . . 12 ?
N2 C3 S2 C2 -57(3) 9_565 . . 12 ?
S2 C3 S2 C2 -24.4(15) 9_565 . . 12 ?
S2 C3 S2 C2 -4(5) 4_565 . . 12 ?
C2 C3 S2 C3 -121(3) 9_565 . . 9_565 ?
C2 C3 S2 C3 -65(2) 4_565 . . 9_565 ?
C4 C3 S2 C3 -149(4) 4_565 . . 9_565 ?
C4 C3 S2 C3 -44(4) 9_565 . . 9_565 ?
N2 C3 S2 C3 71.1(12) 12 . . 9_565 ?
N2 C3 S2 C3 14.1(8) . . . 9_565 ?
S2 C3 S2 C3 -5.8(8) 12 . . 9_565 ?
N2 C3 S2 C3 -14.9(10) 4_565 . . 9_565 ?
N2 C3 S2 C3 -33(2) 9_565 . . 9_565 ?
S2 C3 S2 C3 0.0(12) 9_565 . . 9_565 ?
S2 C3 S2 C3 20(5) 4_565 . . 9_565 ?
C2 C3 S2 C2 -56(4) 9_565 . . 4_565 ?
C4 C3 S2 C2 -84(5) 4_565 . . 4_565 ?
C4 C3 S2 C2 21(2) 9_565 . . 4_565 ?
N2 C3 S2 C2 136(2) 12 . . 4_565 ?
N2 C3 S2 C2 79(3) . . . 4_565 ?
S2 C3 S2 C2 60(3) 12 . . 4_565 ?
N2 C3 S2 C2 50(2) 4_565 . . 4_565 ?
N2 C3 S2 C2 33(3) 9_565 . . 4_565 ?
S2 C3 S2 C2 65(2) 9_565 . . 4_565 ?
S2 C3 S2 C2 86(5) 4_565 . . 4_565 ?
S2 S2 C4 C2 128(17) 4_565 . . 12 ?
N2 S2 C4 C2 13(4) 12 . . 12 ?
N2 S2 C4 C2 -126(6) 9_565 . . 12 ?
C4 S2 C4 C2 -53(6) 4_565 . . 12 ?
C2 S2 C4 C2 -70(5) 9_565 . . 12 ?
C3 S2 C4 C2 -40(5) . . . 12 ?
C3 S2 C4 C2 -74(5) 9_565 . . 12 ?
C2 S2 C4 C2 -61(5) 4_565 . . 12 ?
S2 S2 C4 C3 -158(17) 4_565 . . 9_565 ?
N2 S2 C4 C3 87(2) 12 . . 9_565 ?
N2 S2 C4 C3 -52.2(15) 9_565 . . 9_565 ?
C4 S2 C4 C3 21(4) 4_565 . . 9_565 ?
C2 S2 C4 C3 4(2) 9_565 . . 9_565 ?
C3 S2 C4 C3 33.3(15) . . . 9_565 ?
C2 S2 C4 C3 74(5) 12 . . 9_565 ?
C2 S2 C4 C3 13.0(10) 4_565 . . 9_565 ?
N2 S2 C4 S2 -115(15) 12 . . 4_565 ?
N2 S2 C4 S2 106(16) 9_565 . . 4_565 ?
C4 S2 C4 S2 179(19) 4_565 . . 4_565 ?
C2 S2 C4 S2 162(18) 9_565 . . 4_565 ?
C3 S2 C4 S2 -169(16) . . . 4_565 ?
C2 S2 C4 S2 -128(17) 12 . . 4_565 ?
C3 S2 C4 S2 158(17) 9_565 . . 4_565 ?
C2 S2 C4 S2 171(16) 4_565 . . 4_565 ?
S2 S2 C4 N2 -106(16) 4_565 . . 9_565 ?
N2 S2 C4 N2 139(3) 12 . . 9_565 ?
C4 S2 C4 N2 73(4) 4_565 . . 9_565 ?
C2 S2 C4 N2 56(3) 9_565 . . 9_565 ?
C3 S2 C4 N2 85(2) . . . 9_565 ?
C2 S2 C4 N2 126(6) 12 . . 9_565 ?
C3 S2 C4 N2 52.2(15) 9_565 . . 9_565 ?
C2 S2 C4 N2 65.3(17) 4_565 . . 9_565 ?
S2 S2 C4 N2 115(15) 4_565 . . 12 ?
N2 S2 C4 N2 -139(3) 9_565 . . 12 ?
C4 S2 C4 N2 -66(5) 4_565 . . 12 ?
C2 S2 C4 N2 -83(3) 9_565 . . 12 ?
C3 S2 C4 N2 -53.6(17) . . . 12 ?
C2 S2 C4 N2 -13(4) 12 . . 12 ?
C3 S2 C4 N2 -87(2) 9_565 . . 12 ?
C2 S2 C4 N2 -73.8(18) 4_565 . . 12 ?
S2 S2 C4 C2 170(16) 4_565 . . . ?
N2 S2 C4 C2 54.6(17) 12 . . . ?
N2 S2 C4 C2 -84(2) 9_565 . . . ?
C4 S2 C4 C2 -12(4) 4_565 . . . ?
C2 S2 C4 C2 -29(2) 9_565 . . . ?
C3 S2 C4 C2 1.0 . . . . ?
C2 S2 C4 C2 42(5) 12 . . . ?
C3 S2 C4 C2 -32.2(15) 9_565 . . . ?
C2 S2 C4 C2 -19.2(12) 4_565 . . . ?
S2 S2 C4 C4 -179(16) 4_565 . . 12 ?
N2 S2 C4 C4 66.1(17) 12 . . 12 ?
N2 S2 C4 C4 -73(2) 9_565 . . 12 ?
C4 S2 C4 C4 0(4) 4_565 . . 12 ?
C2 S2 C4 C4 -17(2) 9_565 . . 12 ?
C3 S2 C4 C4 12.5 . . . 12 ?
C2 S2 C4 C4 53(5) 12 . . 12 ?
C3 S2 C4 C4 -20.8(15) 9_565 . . 12 ?
C2 S2 C4 C4 -7.7(12) 4_565 . . 12 ?
C2 C4 C2 C4 180.0 12 . . 12 ?
C3 C4 C2 C4 11.1(19) 9_565 . . 12 ?
S2 C4 C2 C4 85(2) 4_565 . . 12 ?
N2 C4 C2 C4 60.6(18) 9_565 . . 12 ?
N2 C4 C2 C4 100.32(13) 12 . . 12 ?
S2 C4 C2 C4 83.9 . . . 12 ?
C2 C4 C2 C3 168.9(19) 12 . . 9_565 ?
S2 C4 C2 C3 74(3) 4_565 . . 9_565 ?
N2 C4 C2 C3 49(3) 9_565 . . 9_565 ?
N2 C4 C2 C3 89.2(19) 12 . . 9_565 ?
S2 C4 C2 C3 72.7(19) . . . 9_565 ?
C4 C4 C2 C3 -11.1(19) 12 . . 9_565 ?
C2 C4 C2 S2 121(2) 12 . . 9_565 ?
C3 C4 C2 S2 -47(2) 9_565 . . 9_565 ?
S2 C4 C2 S2 27(4) 4_565 . . 9_565 ?
N2 C4 C2 S2 2(3) 9_565 . . 9_565 ?
N2 C4 C2 S2 42(2) 12 . . 9_565 ?
S2 C4 C2 S2 25(2) . . . 9_565 ?
C4 C4 C2 S2 -59(2) 12 . . 9_565 ?
C3 C4 C2 C2 -168.9(19) 9_565 . . 12 ?
S2 C4 C2 C2 -95(2) 4_565 . . 12 ?
N2 C4 C2 C2 -119.4(18) 9_565 . . 12 ?
N2 C4 C2 C2 -79.68(13) 12 . . 12 ?
S2 C4 C2 C2 -96.1 . . . 12 ?
C4 C4 C2 C2 180.0 12 . . 12 ?
C2 C4 C2 N2 134.0(15) 12 . . 4_565 ?
C3 C4 C2 N2 -34.9(15) 9_565 . . 4_565 ?
S2 C4 C2 N2 39(3) 4_565 . . 4_565 ?
N2 C4 C2 N2 15(3) 9_565 . . 4_565 ?
N2 C4 C2 N2 54.3(15) 12 . . 4_565 ?
S2 C4 C2 N2 37.9(15) . . . 4_565 ?
C4 C4 C2 N2 -46.0(15) 12 . . 4_565 ?
C2 C4 C2 N2 96.7 12 . . . ?
C3 C4 C2 N2 -72.2(19) 9_565 . . . ?
S2 C4 C2 N2 2(2) 4_565 . . . ?
N2 C4 C2 N2 -22.8(18) 9_565 . . . ?
N2 C4 C2 N2 16.97(13) 12 . . . ?
S2 C4 C2 N2 0.5 . . . . ?
C4 C4 C2 N2 -83.3 12 . . . ?
C2 C4 C2 S2 114.61(18) 12 . . 12 ?
C3 C4 C2 S2 -54(2) 9_565 . . 12 ?
S2 C4 C2 S2 20(2) 4_565 . . 12 ?
N2 C4 C2 S2 -4.8(17) 9_565 . . 12 ?
N2 C4 C2 S2 34.9(2) 12 . . 12 ?
S2 C4 C2 S2 18.49(18) . . . 12 ?
C4 C4 C2 S2 -65.39(19) 12 . . 12 ?
C2 C4 C2 S2 95(2) 12 . . 4_565 ?
C3 C4 C2 S2 -74(3) 9_565 . . 4_565 ?
N2 C4 C2 S2 -24.9(10) 9_565 . . 4_565 ?
N2 C4 C2 S2 15(2) 12 . . 4_565 ?
S2 C4 C2 S2 -2(2) . . . 4_565 ?
C4 C4 C2 S2 -85(2) 12 . . 4_565 ?
C2 C3 N2 S2 -56(2) 9_565 . . 12 ?
C2 C3 N2 S2 10(2) 4_565 . . 12 ?
C4 C3 N2 S2 -91(4) 4_565 . . 12 ?
C4 C3 N2 S2 30(3) 9_565 . . 12 ?
N2 C3 N2 S2 -126.4(17) 12 . . 12 ?
S2 C3 N2 S2 -110.1(17) . . . 12 ?
N2 C3 N2 S2 -41.1(17) 4_565 . . 12 ?
N2 C3 N2 S2 -95.3(14) 9_565 . . 12 ?
S2 C3 N2 S2 -43(5) 9_565 . . 12 ?
S2 C3 N2 S2 -111.4(15) 4_565 . . 12 ?
C2 C3 N2 S2 -13(6) 9_565 . . 9_565 ?
C2 C3 N2 S2 53(6) 4_565 . . 9_565 ?
C4 C3 N2 S2 -48(6) 4_565 . . 9_565 ?
C4 C3 N2 S2 73(6) 9_565 . . 9_565 ?
N2 C3 N2 S2 -84(6) 12 . . 9_565 ?
S2 C3 N2 S2 -67(6) . . . 9_565 ?
S2 C3 N2 S2 43(5) 12 . . 9_565 ?
N2 C3 N2 S2 2(4) 4_565 . . 9_565 ?
N2 C3 N2 S2 -52(6) 9_565 . . 9_565 ?
S2 C3 N2 S2 -69(6) 4_565 . . 9_565 ?
C2 C3 N2 N2 -15(3) 9_565 . . 4_565 ?
C2 C3 N2 N2 51(2) 4_565 . . 4_565 ?
C4 C3 N2 N2 -49(5) 4_565 . . 4_565 ?
C4 C3 N2 N2 72(4) 9_565 . . 4_565 ?
N2 C3 N2 N2 -85.2(18) 12 . . 4_565 ?
S2 C3 N2 N2 -69.0(18) . . . 4_565 ?
S2 C3 N2 N2 41.1(17) 12 . . 4_565 ?
N2 C3 N2 N2 -54(2) 9_565 . . 4_565 ?
S2 C3 N2 N2 -2(4) 9_565 . . 4_565 ?
S2 C3 N2 N2 -70(2) 4_565 . . 4_565 ?
C2 C3 N2 C4 -86(4) 9_565 . . 9_565 ?
C2 C3 N2 C4 -20.2(13) 4_565 . . 9_565 ?
C4 C3 N2 C4 -121(6) 4_565 . . 9_565 ?
N2 C3 N2 C4 -157(3) 12 . . 9_565 ?
S2 C3 N2 C4 -140(3) . . . 9_565 ?
S2 C3 N2 C4 -30(3) 12 . . 9_565 ?
N2 C3 N2 C4 -72(4) 4_565 . . 9_565 ?
N2 C3 N2 C4 -126(3) 9_565 . . 9_565 ?
S2 C3 N2 C4 -73(6) 9_565 . . 9_565 ?
S2 C3 N2 C4 -142(3) 4_565 . . 9_565 ?
C2 C3 N2 C4 41(3) 9_565 . . 12 ?
C2 C3 N2 C4 108(2) 4_565 . . 12 ?
C4 C3 N2 C4 7(4) 4_565 . . 12 ?
C4 C3 N2 C4 128(3) 9_565 . . 12 ?
N2 C3 N2 C4 -29.1(7) 12 . . 12 ?
S2 C3 N2 C4 -12.8(7) . . . 12 ?
S2 C3 N2 C4 97.3(10) 12 . . 12 ?
N2 C3 N2 C4 56.2(13) 4_565 . . 12 ?
N2 C3 N2 C4 2.1(12) 9_565 . . 12 ?
S2 C3 N2 C4 55(5) 9_565 . . 12 ?
S2 C3 N2 C4 -14.1(13) 4_565 . . 12 ?
C2 C3 N2 C2 -66(3) 9_565 . . 4_565 ?
C4 C3 N2 C2 -101(6) 4_565 . . 4_565 ?
C4 C3 N2 C2 20.2(13) 9_565 . . 4_565 ?
N2 C3 N2 C2 -137(2) 12 . . 4_565 ?
S2 C3 N2 C2 -120(2) . . . 4_565 ?
S2 C3 N2 C2 -10(2) 12 . . 4_565 ?
N2 C3 N2 C2 -51(2) 4_565 . . 4_565 ?
N2 C3 N2 C2 -105(2) 9_565 . . 4_565 ?
S2 C3 N2 C2 -53(6) 9_565 . . 4_565 ?
S2 C3 N2 C2 -122(2) 4_565 . . 4_565 ?
C2 C3 N2 C2 57(3) 9_565 . . . ?
C2 C3 N2 C2 123(2) 4_565 . . . ?
C4 C3 N2 C2 22(5) 4_565 . . . ?
C4 C3 N2 C2 143(3) 9_565 . . . ?
N2 C3 N2 C2 -13.5 12 . . . ?
S2 C3 N2 C2 2.8 . . . . ?
S2 C3 N2 C2 112.8(17) 12 . . . ?
N2 C3 N2 C2 71.7(18) 4_565 . . . ?
N2 C3 N2 C2 17.6(13) 9_565 . . . ?
S2 C3 N2 C2 70(6) 9_565 . . . ?
S2 C3 N2 C2 1.4(12) 4_565 . . . ?
C2 C3 N2 C3 39(2) 9_565 . . 9_565 ?
C2 C3 N2 C3 105(3) 4_565 . . 9_565 ?
C4 C3 N2 C3 5(4) 4_565 . . 9_565 ?
C4 C3 N2 C3 126(4) 9_565 . . 9_565 ?
N2 C3 N2 C3 -31.1(9) 12 . . 9_565 ?
S2 C3 N2 C3 -14.8(9) . . . 9_565 ?
S2 C3 N2 C3 95.3(15) 12 . . 9_565 ?
N2 C3 N2 C3 54.1(13) 4_565 . . 9_565 ?
N2 C3 N2 C3 0.0(11) 9_565 . . 9_565 ?
S2 C3 N2 C3 52(5) 9_565 . . 9_565 ?
S2 C3 N2 C3 -16.2(11) 4_565 . . 9_565 ?
C4 C2 N2 S2 -13(3) 12 . . 12 ?
C3 C2 N2 S2 70(2) 9_565 . . 12 ?
S2 C2 N2 S2 -17(4) 9_565 . . 12 ?
C2 C2 N2 S2 115(3) 12 . . 12 ?
N2 C2 N2 S2 18(3) 4_565 . . 12 ?
C4 C2 N2 S2 103(3) . . . 12 ?
S2 C2 N2 S2 104(3) 4_565 . . 12 ?
C4 C2 N2 S2 4(6) 12 . . 9_565 ?
C3 C2 N2 S2 87(5) 9_565 . . 9_565 ?
C2 C2 N2 S2 132(5) 12 . . 9_565 ?
N2 C2 N2 S2 35(4) 4_565 . . 9_565 ?
C4 C2 N2 S2 120(5) . . . 9_565 ?
S2 C2 N2 S2 17(4) 12 . . 9_565 ?
S2 C2 N2 S2 121(4) 4_565 . . 9_565 ?
C4 C2 N2 N2 -32(6) 12 . . 4_565 ?
C3 C2 N2 N2 51(2) 9_565 . . 4_565 ?
S2 C2 N2 N2 -35(4) 9_565 . . 4_565 ?
C2 C2 N2 N2 96.1(8) 12 . . 4_565 ?
C4 C2 N2 N2 84.6(8) . . . 4_565 ?
S2 C2 N2 N2 -18(3) 12 . . 4_565 ?
S2 C2 N2 N2 85.5(13) 4_565 . . 4_565 ?
C4 C2 N2 C4 -79(6) 12 . . 9_565 ?
C3 C2 N2 C4 3.2(17) 9_565 . . 9_565 ?
S2 C2 N2 C4 -83(6) 9_565 . . 9_565 ?
C2 C2 N2 C4 48(2) 12 . . 9_565 ?
N2 C2 N2 C4 -48(2) 4_565 . . 9_565 ?
C4 C2 N2 C4 37(2) . . . 9_565 ?
S2 C2 N2 C4 -66(3) 12 . . 9_565 ?
S2 C2 N2 C4 38(2) 4_565 . . 9_565 ?
C3 C2 N2 C4 83(5) 9_565 . . 12 ?
S2 C2 N2 C4 -4(6) 9_565 . . 12 ?
C2 C2 N2 C4 128(6) 12 . . 12 ?
N2 C2 N2 C4 32(6) 4_565 . . 12 ?
C4 C2 N2 C4 116(6) . . . 12 ?
S2 C2 N2 C4 13(3) 12 . . 12 ?
S2 C2 N2 C4 117(6) 4_565 . . 12 ?
C4 C2 N2 C3 -118(6) 12 . . . ?
C3 C2 N2 C3 -35.6(14) 9_565 . . . ?
S2 C2 N2 C3 -122(5) 9_565 . . . ?
C2 C2 N2 C3 9.4 12 . . . ?
N2 C2 N2 C3 -86.7(8) 4_565 . . . ?
C4 C2 N2 C3 -2.1 . . . . ?
S2 C2 N2 C3 -105(3) 12 . . . ?
S2 C2 N2 C3 -1.2(10) 4_565 . . . ?
C4 C2 N2 C2 -79(6) 12 . . 4_565 ?
C3 C2 N2 C2 4.1(14) 9_565 . . 4_565 ?
S2 C2 N2 C2 -82(5) 9_565 . . 4_565 ?
C2 C2 N2 C2 49.2(15) 12 . . 4_565 ?
N2 C2 N2 C2 -46.9(18) 4_565 . . 4_565 ?
C4 C2 N2 C2 37.6(15) . . . 4_565 ?
S2 C2 N2 C2 -65(3) 12 . . 4_565 ?
S2 C2 N2 C2 38.5(18) 4_565 . . 4_565 ?
C4 C2 N2 C3 -83(5) 12 . . 9_565 ?
S2 C2 N2 C3 -87(5) 9_565 . . 9_565 ?
C2 C2 N2 C3 45.0(14) 12 . . 9_565 ?
N2 C2 N2 C3 -51(2) 4_565 . . 9_565 ?
C4 C2 N2 C3 33.5(14) . . . 9_565 ?
S2 C2 N2 C3 -70(2) 12 . . 9_565 ?
S2 C2 N2 C3 34.4(13) 4_565 . . 9_565 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A Cl1 0.86 2.52 3.307(3) 153.1 5_545
N1 H1B S1 0.86 2.54 3.396(4) 175.0 13_565

_refine_diff_density_max         1.003
_refine_diff_density_min         -0.889
_refine_diff_density_rms         0.088

####################################################################### 
# 
# 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_133K
_database_code_depnum_ccdc_archive 'CCDC 1432880'
_audit_update_record             
;
2016-03-17 deposited with the CCDC.
2016-11-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C3 H4 N S, 2(C H4 N2 S), Cl'
_chemical_formula_sum            'C5 H12 Cl N5 S3'
_chemical_formula_weight         273.83

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
Cl Cl 0.1484 0.1585 '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      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P m c n'
_space_group_name_Hall           '-P 2n 2a'

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

_cell_length_a                   14.311(10)
_cell_length_b                   10.228(7)
_cell_length_c                   8.393(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1228.5(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    133(2)
_cell_measurement_reflns_used    2756
_cell_measurement_theta_min      3.4459
_cell_measurement_theta_max      27.4507

_exptl_crystal_description       needlelike
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_F_000             568
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    0.793
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?

_exptl_absorpt_correction_T_min  0.9074
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_type   Multi-scan

_exptl_absorpt_process_details   
;   Higashi, T.(1995). Program for Absorption Correction.
    Rigaku Corporation, Tokyo, Japan. 
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      133(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Saturn724+ (4x4 bin mode)'
_diffrn_measurement_method       CCD_Profile_fitting
_diffrn_detector_area_resol_mean 28.5714

_diffrn_reflns_number            8314
_diffrn_reflns_av_unetI/netI     0.0228
_diffrn_reflns_av_R_equivalents  0.0426
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.448
_diffrn_reflns_theta_max         27.451
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             1461
_reflns_number_gt                1247
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0489P)²+0.9872P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1461
_refine_ls_number_parameters     85
_refine_ls_number_restraints     42
_refine_ls_R_factor_all          0.0622
_refine_ls_R_factor_gt           0.0517
_refine_ls_wR_factor_ref         0.1239
_refine_ls_wR_factor_gt          0.1183
_refine_ls_goodness_of_fit_ref   1.224
_refine_ls_restrained_S_all      1.208
_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 1.06431(16) 0.0777(2) 0.7498(3) 0.0185(5) Uani 1 1 d . . . . .
C2 C 0.7238(5) 0.1313(8) 0.5680(11) 0.033(2) Uani 0.5 1 d . U P . .
H5A H 0.7007 0.0531 0.5975 0.040 Uiso 0.5 1 d R U P . .
C3 C 0.8248(8) 0.2891(9) 0.5341(12) 0.038(2) Uani 0.5 1 d . U P . .
H4B H 0.8850 0.3305 0.5396 0.045 Uiso 0.5 1 d R U P . .
C4 C 0.7500 0.3499(4) 0.4825(5) 0.0372(10) Uani 1 2 d S TU P . .
H4A H 0.7500 0.4320 0.4439 0.045 Uiso 1 2 d R U P . .
Cl1 Cl 0.7500 -0.16378(7) 0.75645(10) 0.0194(2) Uani 1 2 d S T P . .
N1 N 1.09872(14) 0.12304(19) 0.6140(2) 0.0249(5) Uani 1 1 d . . . . .
H1A H 1.1462 0.1745 0.6150 0.030 Uiso 1 1 d R U . . .
H1B H 1.0735 0.1010 0.5250 0.030 Uiso 1 1 d R U . . .
N2 N 1.10520(14) 0.11419(18) 0.8840(2) 0.0223(5) Uani 1 1 d . . . . .
H2A H 1.1526 0.1658 0.8814 0.027 Uiso 1 1 d R U . . .
H2B H 1.0844 0.0863 0.9739 0.027 Uiso 1 1 d R U . . .
N3 N 0.8100(5) 0.1623(7) 0.5805(8) 0.0314(15) Uani 0.5 1 d . U P . .
H3B H 0.8555 0.1076 0.6126 0.038 Uiso 0.5 1 d R U P . .
S1 S 0.97033(5) -0.02583(7) 0.75140(7) 0.0291(2) Uani 1 1 d . . . . .
S2 S 0.65582(19) 0.2532(2) 0.4974(4) 0.0424(6) Uani 0.5 1 d . U P . .


_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 N2 1.323(3) . ?
C1 N1 1.325(3) . ?
C1 S1 1.712(2) . ?
C2 N3 0.587(8) 8_755 ?
C2 C2 0.749(15) 8_755 ?
C2 N3 1.277(8) . ?
C2 S2 1.689(8) . ?
C2 C3 1.781(14) 8_755 ?
C2 S2 2.207(9) 8_755 ?
C2 H5A 0.9000 . ?
C3 S2 0.554(7) 8_755 ?
C3 C4 1.312(11) . ?
C3 N3 1.372(11) . ?
C3 C2 1.781(14) 8_755 ?
C3 H4B 0.9600 . ?
C4 C3 1.312(11) 8_755 ?
C4 S2 1.677(3) . ?
C4 S2 1.677(3) 8_755 ?
C4 H4A 0.9000 . ?
N1 H1A 0.8595 . ?
N1 H1B 0.8597 . ?
N2 H2A 0.8596 . ?
N2 H2B 0.8599 . ?
N3 C2 0.587(8) 8_755 ?
N3 S2 1.262(8) 8_755 ?
N3 N3 1.716(15) 8_755 ?
N3 H3B 0.9000 . ?
S2 C3 0.554(7) 8_755 ?
S2 N3 1.262(8) 8_755 ?
S2 C2 2.207(9) 8_755 ?

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
N2 C1 N1 118.0(2) . . ?
N2 C1 S1 121.04(17) . . ?
N1 C1 S1 121.00(17) . . ?
N3 C2 C2 145.4(16) 8_755 8_755 ?
N3 C2 N3 130(2) 8_755 . ?
C2 C2 N3 15.2(6) 8_755 . ?
N3 C2 S2 36.0(13) 8_755 . ?
C2 C2 S2 125.2(3) 8_755 . ?
N3 C2 S2 113.7(9) . . ?
N3 C2 C3 38.6(14) 8_755 8_755 ?
C2 C2 C3 113.0(4) 8_755 8_755 ?
N3 C2 C3 99.5(9) . 8_755 ?
S2 C2 C3 18.1(3) . 8_755 ?
N3 C2 S2 112.7(17) 8_755 8_755 ?
C2 C2 S2 38.7(2) 8_755 8_755 ?
N3 C2 S2 29.4(5) . 8_755 ?
S2 C2 S2 86.5(4) . 8_755 ?
C3 C2 S2 75.5(5) 8_755 8_755 ?
N3 C2 H5A 97.3 8_755 . ?
C2 C2 H5A 111.6 8_755 . ?
N3 C2 H5A 123.6 . . ?
S2 C2 H5A 122.7 . . ?
C3 C2 H5A 134.9 8_755 . ?
S2 C2 H5A 149.6 8_755 . ?
S2 C3 C4 122.6(18) 8_755 . ?
S2 C3 N3 66.9(13) 8_755 . ?
C4 C3 N3 114.6(10) . . ?
S2 C3 C2 71.5(14) 8_755 8_755 ?
C4 C3 C2 99.4(8) . 8_755 ?
N3 C3 C2 15.5(5) . 8_755 ?
S2 C3 H4B 82.6 8_755 . ?
C4 C3 H4B 122.6 . . ?
N3 C3 H4B 122.8 . . ?
C2 C3 H4B 137.9 8_755 . ?
C3 C4 C3 109.4(10) 8_755 . ?
C3 C4 S2 16.2(4) 8_755 . ?
C3 C4 S2 110.6(5) . . ?
C3 C4 S2 110.6(5) 8_755 8_755 ?
C3 C4 S2 16.2(4) . 8_755 ?
S2 C4 S2 107.0(3) . 8_755 ?
C3 C4 H4A 124.1 8_755 . ?
C3 C4 H4A 124.1 . . ?
S2 C4 H4A 125.3 . . ?
S2 C4 H4A 125.3 8_755 . ?
C1 N1 H1A 120.0 . . ?
C1 N1 H1B 120.0 . . ?
H1A N1 H1B 120.1 . . ?
C1 N2 H2A 120.0 . . ?
C1 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
C2 N3 S2 128.2(17) 8_755 8_755 ?
C2 N3 C2 19.5(11) 8_755 . ?
S2 N3 C2 120.8(9) 8_755 . ?
C2 N3 C3 126.0(19) 8_755 . ?
S2 N3 C3 23.8(4) 8_755 . ?
C2 N3 C3 111.2(10) . . ?
C2 N3 N3 34.6(16) 8_755 8_755 ?
S2 N3 N3 112.9(4) 8_755 8_755 ?
C2 N3 N3 15.2(6) . 8_755 ?
C3 N3 N3 98.9(6) . 8_755 ?
C2 N3 H3B 108.3 8_755 . ?
S2 N3 H3B 110.0 8_755 . ?
C2 N3 H3B 124.7 . . ?
C3 N3 H3B 124.1 . . ?
N3 N3 H3B 136.4 8_755 . ?
C3 S2 N3 89.3(14) 8_755 8_755 ?
C3 S2 C4 41.2(14) 8_755 . ?
N3 S2 C4 99.4(4) 8_755 . ?
C3 S2 C2 90.4(15) 8_755 . ?
N3 S2 C2 15.9(5) 8_755 . ?
C4 S2 C2 89.9(4) . . ?
C3 S2 C2 80.5(15) 8_755 8_755 ?
N3 S2 C2 29.8(4) 8_755 8_755 ?
C4 S2 C2 74.1(3) . 8_755 ?
C2 S2 C2 16.1(3) . 8_755 ?

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
S2 C3 C4 C3 97(2) 8_755 . . 8_755 ?
N3 C3 C4 C3 19.8(11) . . . 8_755 ?
C2 C3 C4 C3 23.1(10) 8_755 . . 8_755 ?
S2 C3 C4 S2 80(2) 8_755 . . . ?
N3 C3 C4 S2 2.6(8) . . . . ?
C2 C3 C4 S2 5.9(7) 8_755 . . . ?
N3 C3 C4 S2 -77(2) . . . 8_755 ?
C2 C3 C4 S2 -74.0(19) 8_755 . . 8_755 ?
N3 C2 N3 C2 179.999(12) 8_755 . . 8_755 ?
S2 C2 N3 C2 -142(2) . . . 8_755 ?
C3 C2 N3 C2 -154(2) 8_755 . . 8_755 ?
S2 C2 N3 C2 -118(3) 8_755 . . 8_755 ?
N3 C2 N3 S2 -62(3) 8_755 . . 8_755 ?
C2 C2 N3 S2 118(3) 8_755 . . 8_755 ?
S2 C2 N3 S2 -23.7(13) . . . 8_755 ?
C3 C2 N3 S2 -35.5(12) 8_755 . . 8_755 ?
N3 C2 N3 C3 -37(3) 8_755 . . . ?
C2 C2 N3 C3 143(3) 8_755 . . . ?
S2 C2 N3 C3 0.7(11) . . . . ?
C3 C2 N3 C3 -11.2(9) 8_755 . . . ?
S2 C2 N3 C3 24.3(5) 8_755 . . . ?
C2 C2 N3 N3 180.001(11) 8_755 . . 8_755 ?
S2 C2 N3 N3 38(2) . . . 8_755 ?
C3 C2 N3 N3 26(2) 8_755 . . 8_755 ?
S2 C2 N3 N3 62(3) 8_755 . . 8_755 ?
S2 C3 N3 C2 -104(3) 8_755 . . 8_755 ?
C4 C3 N3 C2 12(2) . . . 8_755 ?
C4 C3 N3 S2 116.7(18) . . . 8_755 ?
C2 C3 N3 S2 104(3) 8_755 . . 8_755 ?
S2 C3 N3 C2 -118.9(16) 8_755 . . . ?
C4 C3 N3 C2 -2.1(11) . . . . ?
C2 C3 N3 C2 -14.5(14) 8_755 . . . ?
S2 C3 N3 N3 -128.1(14) 8_755 . . 8_755 ?
C4 C3 N3 N3 -11.4(7) . . . 8_755 ?
C2 C3 N3 N3 -24(2) 8_755 . . 8_755 ?
C3 C4 S2 C3 89(2) . . . 8_755 ?
S2 C4 S2 C3 106(2) 8_755 . . 8_755 ?
C3 C4 S2 N3 -78(2) 8_755 . . 8_755 ?
C3 C4 S2 N3 10.9(5) . . . 8_755 ?
S2 C4 S2 N3 27.6(5) 8_755 . . 8_755 ?
C3 C4 S2 C2 -91(2) 8_755 . . . ?
C3 C4 S2 C2 -1.8(6) . . . . ?
S2 C4 S2 C2 14.8(4) 8_755 . . . ?
C3 C4 S2 C2 -94(2) 8_755 . . 8_755 ?
C3 C4 S2 C2 -4.9(5) . . . 8_755 ?
S2 C4 S2 C2 11.7(3) 8_755 . . 8_755 ?
N3 C2 S2 C3 86(3) 8_755 . . 8_755 ?
C2 C2 S2 C3 -51.9(15) 8_755 . . 8_755 ?
N3 C2 S2 C3 -40.6(16) . . . 8_755 ?
S2 C2 S2 C3 -51.9(15) 8_755 . . 8_755 ?
C2 C2 S2 N3 -138(2) 8_755 . . 8_755 ?
N3 C2 S2 N3 -127(3) . . . 8_755 ?
C3 C2 S2 N3 -86(3) 8_755 . . 8_755 ?
S2 C2 S2 N3 -138(2) 8_755 . . 8_755 ?
N3 C2 S2 C4 127(2) 8_755 . . . ?
C2 C2 S2 C4 -10.7(3) 8_755 . . . ?
N3 C2 S2 C4 0.7(9) . . . . ?
C3 C2 S2 C4 41.2(14) 8_755 . . . ?
S2 C2 S2 C4 -10.7(3) 8_755 . . . ?
N3 C2 S2 C2 138(2) 8_755 . . 8_755 ?
N3 C2 S2 C2 11.4(6) . . . 8_755 ?
C3 C2 S2 C2 51.9(15) 8_755 . . 8_755 ?
S2 C2 S2 C2 -0.001(2) 8_755 . . 8_755 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A Cl1 0.86 2.47 3.259(2) 152.8 2_756
N1 H1B S1 0.86 2.52 3.372(3) 169.5 5_756
N2 H2A Cl1 0.86 2.51 3.292(2) 151.0 2_756
N2 H2B S1 0.86 2.51 3.369(3) 174.2 5_757
N3 H3B S1 0.90 2.43 3.320(8) 168.8 .

_refine_diff_density_max         1.095
_refine_diff_density_min         -0.764
_refine_diff_density_rms         0.070

