# 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. 
# 
#######################################################################

data_compound9
_database_code_depnum_ccdc_archive 'CCDC 1410920'
_audit_update_record             
;
2016-08-13 deposited with the CCDC.
2016-09-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H24 N4 O2 S2'
_chemical_formula_sum            'C17 H24 N4 O2 S2'
_chemical_formula_weight         380.52

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c
_symmetry_space_group_name_Hall  -P2ybc

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

_cell_length_a                   8.4757(6)
_cell_length_b                   23.0572(18)
_cell_length_c                   9.7935(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.534(5)
_cell_angle_gamma                90.00
_cell_volume                     1860.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    230(2)
_cell_measurement_reflns_used    19226
_cell_measurement_theta_min      6.813
_cell_measurement_theta_max      56.651

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.55
_exptl_crystal_size_min          0.39
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             808
_exptl_absorpt_coefficient_mu    0.305
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8383
_exptl_absorpt_correction_T_max  0.8904
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      230(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18298
_diffrn_reflns_av_R_equivalents  0.0322
_diffrn_reflns_av_unetI/netI     0.0274
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.77
_diffrn_reflns_theta_max         27.88
_reflns_number_total             4422
_reflns_number_gt                3348
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Apex2, Bruker Instrument Service v2010, 1-2'
_computing_cell_refinement       
'SAINT V7.68A (Bruker: Madison, 2009 ) in Apex2 suite'
_computing_data_reduction        
'SAINT and XPREP Version 2008/2 (Sheldrick, Bruker AXS Inc.)'
_computing_structure_solution    
'XS V2008/1 (G. M. Sheldrick, Acta Cryst. (2008). A64, 112-122)'
_computing_structure_refinement  
'XL V2008/4 (G. M. Sheldrick, Acta Cryst. (2008). A64, 112-122)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0565P)²+0.8059P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4422
_refine_ls_number_parameters     324
_refine_ls_number_restraints     74
_refine_ls_R_factor_all          0.0631
_refine_ls_R_factor_gt           0.0437
_refine_ls_wR_factor_ref         0.1222
_refine_ls_wR_factor_gt          0.1092
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S -0.43585(7) 0.47025(3) -0.24089(6) 0.04986(17) Uani 1 1 d . . .
O1 O 0.1830(2) 0.68448(8) 0.61289(15) 0.0577(5) Uani 1 1 d . A .
C1 C -0.3464(2) 0.53753(10) -0.2507(2) 0.0424(5) Uani 1 1 d . . .
N1 N -0.3599(2) 0.41760(8) 0.0102(2) 0.0521(5) Uani 1 1 d . . .
S2 S 0.09456(7) 0.70825(2) 0.48232(5) 0.04512(16) Uani 1 1 d . . .
N2 N -0.1913(2) 0.46589(8) 0.20673(19) 0.0467(4) Uani 1 1 d . . .
O2 O -0.0359(3) 0.74808(8) 0.4823(2) 0.0714(5) Uani 1 1 d . A .
C2 C -0.3724(3) 0.56867(13) -0.3883(2) 0.0550(6) Uani 1 1 d . . .
H2B H -0.323(3) 0.5462(11) -0.458(3) 0.049(6) Uiso 1 1 d . . .
H2A H -0.486(4) 0.5716(13) -0.430(3) 0.080(9) Uiso 1 1 d . . .
N3 N -0.1029(2) 0.56130(7) 0.20264(16) 0.0364(4) Uani 1 1 d . . .
C3 C -0.3031(4) 0.62906(13) -0.3677(3) 0.0604(7) Uani 1 1 d . . .
H3B H -0.290(4) 0.6440(13) -0.457(3) 0.080(9) Uiso 1 1 d . . .
H3A H -0.385(4) 0.6536(13) -0.333(3) 0.074(9) Uiso 1 1 d . . .
N4 N 0.0160(2) 0.65381(7) 0.38544(17) 0.0401(4) Uani 1 1 d . A .
C4 C -0.1393(3) 0.62957(12) -0.2652(2) 0.0527(6) Uani 1 1 d . . .
H4B H -0.066(3) 0.6017(12) -0.302(3) 0.069(8) Uiso 1 1 d . . .
H4A H -0.090(3) 0.6686(12) -0.260(3) 0.060(7) Uiso 1 1 d . . .
C5 C -0.1528(3) 0.61032(10) -0.1186(2) 0.0431(5) Uani 1 1 d . . .
H5B H -0.046(3) 0.6036(10) -0.060(3) 0.049(6) Uiso 1 1 d . . .
H5A H -0.204(3) 0.6422(11) -0.072(2) 0.048(6) Uiso 1 1 d . . .
C6 C -0.2526(2) 0.55586(9) -0.12583(19) 0.0349(4) Uani 1 1 d . . .
C7 C -0.2548(2) 0.51494(8) -0.0142(2) 0.0341(4) Uani 1 1 d . . .
C8 C -0.3452(2) 0.46521(9) -0.0644(2) 0.0404(5) Uani 1 1 d . . .
C9 C -0.2763(3) 0.42096(11) 0.1416(3) 0.0547(6) Uani 1 1 d . . .
H9 H -0.277(3) 0.3879(13) 0.199(3) 0.068(8) Uiso 1 1 d . . .
C10 C -0.1847(2) 0.51369(8) 0.1316(2) 0.0351(4) Uani 1 1 d . . .
C11 C -0.1993(2) 0.61414(9) 0.2037(2) 0.0352(4) Uani 1 1 d . A .
H11B H -0.268(2) 0.6093(9) 0.274(2) 0.033(5) Uiso 1 1 d . . .
H11A H -0.269(2) 0.6199(9) 0.113(2) 0.033(5) Uiso 1 1 d . . .
C12 C -0.0880(3) 0.66538(9) 0.2456(2) 0.0380(4) Uani 1 1 d . . .
H12B H -0.150(3) 0.6995(10) 0.250(2) 0.038(6) Uiso 1 1 d . . .
H12A H -0.021(3) 0.6716(10) 0.180(2) 0.046(6) Uiso 1 1 d . . .
C13 C 0.1096(3) 0.59988(11) 0.3907(3) 0.0543(6) Uani 1 1 d . . .
H13B H 0.183(3) 0.6036(11) 0.325(3) 0.058(7) Uiso 1 1 d . . .
H13A H 0.173(3) 0.5947(12) 0.486(3) 0.068(8) Uiso 1 1 d . . .
C14 C -0.0041(3) 0.54992(10) 0.3443(2) 0.0503(6) Uani 1 1 d . A .
H14B H -0.080(3) 0.5461(11) 0.410(3) 0.055(7) Uiso 1 1 d . . .
H14A H 0.061(3) 0.5142(11) 0.341(3) 0.055(7) Uiso 1 1 d . . .
C15A C 0.2426(7) 0.7369(4) 0.3962(6) 0.103(2) Uani 0.721(8) 1 d PDU A 1
H15A H 0.1890 0.7369 0.2961 0.124 Uiso 0.721(8) 1 calc PR A 1
H15B H 0.2542 0.7778 0.4242 0.124 Uiso 0.721(8) 1 calc PR A 1
C16A C 0.3764(5) 0.7207(2) 0.4016(6) 0.0845(19) Uani 0.721(8) 1 d PDU A 1
H16A H 0.3683 0.6904 0.3300 0.101 Uiso 0.721(8) 1 calc PR A 1
H16B H 0.4141 0.7016 0.4928 0.101 Uiso 0.721(8) 1 calc PR A 1
C17A C 0.5117(12) 0.7615(6) 0.3840(14) 0.123(5) Uani 0.721(8) 1 d PDU A 1
H17A H 0.4724 0.7864 0.3033 0.185 Uiso 0.721(8) 1 calc PR A 1
H17B H 0.6031 0.7390 0.3697 0.185 Uiso 0.721(8) 1 calc PR A 1
H17C H 0.5456 0.7852 0.4676 0.185 Uiso 0.721(8) 1 calc PR A 1
C15B C 0.2210(10) 0.7551(4) 0.4219(10) 0.0233(17) Uani 0.279(8) 1 d PDU A 2
H15C H 0.2161 0.7421 0.3258 0.028 Uiso 0.279(8) 1 calc PR A 2
H15D H 0.1640 0.7924 0.4126 0.028 Uiso 0.279(8) 1 calc PR A 2
C16B C 0.3722(11) 0.7684(5) 0.4718(10) 0.065(3) Uani 0.279(8) 1 d PDU A 2
H16C H 0.4151 0.7374 0.5387 0.078 Uiso 0.279(8) 1 calc PR A 2
H16D H 0.3699 0.8033 0.5285 0.078 Uiso 0.279(8) 1 calc PR A 2
C17B C 0.504(2) 0.7797(12) 0.394(2) 0.073(5) Uani 0.279(8) 1 d PDU A 2
H17D H 0.4577 0.7795 0.2935 0.109 Uiso 0.279(8) 1 calc PR A 2
H17E H 0.5863 0.7495 0.4168 0.109 Uiso 0.279(8) 1 calc PR A 2
H17F H 0.5539 0.8171 0.4216 0.109 Uiso 0.279(8) 1 calc PR 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
S1 C8 1.723(2) . ?
S1 C1 1.739(2) . ?
O1 S2 1.4314(16) . ?
C1 C6 1.360(3) . ?
C1 C2 1.497(3) . ?
N1 C9 1.319(3) . ?
N1 C8 1.340(3) . ?
S2 O2 1.437(2) . ?
S2 N4 1.6198(17) . ?
S2 C15B 1.720(10) . ?
S2 C15A 1.793(5) . ?
N2 C10 1.334(3) . ?
N2 C9 1.335(3) . ?
C2 C3 1.507(4) . ?
C2 H2B 1.02(2) . ?
C2 H2A 0.96(3) . ?
N3 C10 1.394(3) . ?
N3 C14 1.466(3) . ?
N3 C11 1.468(2) . ?
C3 C4 1.511(4) . ?
C3 H3B 0.97(3) . ?
C3 H3A 1.01(3) . ?
N4 C13 1.469(3) . ?
N4 C12 1.469(2) . ?
C4 C5 1.532(3) . ?
C4 H4B 1.02(3) . ?
C4 H4A 0.99(3) . ?
C5 C6 1.506(3) . ?
C5 H5B 0.96(2) . ?
C5 H5A 1.02(2) . ?
C6 C7 1.447(3) . ?
C7 C8 1.403(3) . ?
C7 C10 1.413(3) . ?
C9 H9 0.95(3) . ?
C11 C12 1.507(3) . ?
C11 H11B 1.01(2) . ?
C11 H11A 0.95(2) . ?
C12 H12B 0.95(2) . ?
C12 H12A 0.96(2) . ?
C13 C14 1.502(4) . ?
C13 H13B 1.00(3) . ?
C13 H13A 0.97(3) . ?
C14 H14B 1.01(3) . ?
C14 H14A 1.00(3) . ?
C15A C16A 1.184(7) . ?
C15A H15A 0.9800 . ?
C15A H15B 0.9800 . ?
C16A C17A 1.524(8) . ?
C16A H16A 0.9800 . ?
C16A H16B 0.9800 . ?
C17A H17A 0.9700 . ?
C17A H17B 0.9700 . ?
C17A H17C 0.9700 . ?
C15B C16B 1.297(11) . ?
C15B H15C 0.9800 . ?
C15B H15D 0.9800 . ?
C16B C17B 1.519(15) . ?
C16B H16C 0.9800 . ?
C16B H16D 0.9800 . ?
C17B H17D 0.9700 . ?
C17B H17E 0.9700 . ?
C17B H17F 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
C8 S1 C1 91.01(10) . . ?
C6 C1 C2 126.3(2) . . ?
C6 C1 S1 113.46(16) . . ?
C2 C1 S1 120.21(17) . . ?
C9 N1 C8 112.8(2) . . ?
O1 S2 O2 119.13(11) . . ?
O1 S2 N4 106.51(10) . . ?
O2 S2 N4 106.53(10) . . ?
O1 S2 C15B 108.0(3) . . ?
O2 S2 C15B 98.0(3) . . ?
N4 S2 C15B 119.2(3) . . ?
O1 S2 C15A 106.5(2) . . ?
O2 S2 C15A 112.8(3) . . ?
N4 S2 C15A 104.3(3) . . ?
C15B S2 C15A 17.6(4) . . ?
C10 N2 C9 117.7(2) . . ?
C1 C2 C3 110.6(2) . . ?
C1 C2 H2B 111.0(14) . . ?
C3 C2 H2B 110.5(14) . . ?
C1 C2 H2A 109.6(18) . . ?
C3 C2 H2A 108.4(19) . . ?
H2B C2 H2A 107(2) . . ?
C10 N3 C14 116.02(17) . . ?
C10 N3 C11 116.39(15) . . ?
C14 N3 C11 109.70(16) . . ?
C2 C3 C4 111.4(2) . . ?
C2 C3 H3B 109.2(18) . . ?
C4 C3 H3B 108.5(18) . . ?
C2 C3 H3A 106.6(17) . . ?
C4 C3 H3A 111.5(16) . . ?
H3B C3 H3A 110(2) . . ?
C13 N4 C12 112.81(16) . . ?
C13 N4 S2 119.40(14) . . ?
C12 N4 S2 118.68(14) . . ?
C3 C4 C5 111.2(2) . . ?
C3 C4 H4B 107.6(15) . . ?
C5 C4 H4B 109.6(16) . . ?
C3 C4 H4A 110.8(15) . . ?
C5 C4 H4A 110.0(15) . . ?
H4B C4 H4A 107(2) . . ?
C6 C5 C4 111.21(18) . . ?
C6 C5 H5B 109.5(14) . . ?
C4 C5 H5B 109.8(14) . . ?
C6 C5 H5A 109.3(13) . . ?
C4 C5 H5A 110.4(13) . . ?
H5B C5 H5A 106.6(19) . . ?
C1 C6 C7 111.61(18) . . ?
C1 C6 C5 120.31(18) . . ?
C7 C6 C5 127.89(17) . . ?
C8 C7 C10 113.79(18) . . ?
C8 C7 C6 111.76(17) . . ?
C10 C7 C6 134.43(18) . . ?
N1 C8 C7 126.3(2) . . ?
N1 C8 S1 121.69(16) . . ?
C7 C8 S1 112.03(16) . . ?
N1 C9 N2 128.2(2) . . ?
N1 C9 H9 117.3(17) . . ?
N2 C9 H9 114.6(17) . . ?
N2 C10 N3 117.08(17) . . ?
N2 C10 C7 120.85(18) . . ?
N3 C10 C7 122.06(17) . . ?
N3 C11 C12 109.81(16) . . ?
N3 C11 H11B 109.1(12) . . ?
C12 C11 H11B 109.1(12) . . ?
N3 C11 H11A 109.4(12) . . ?
C12 C11 H11A 110.8(12) . . ?
H11B C11 H11A 108.7(16) . . ?
N4 C12 C11 108.18(17) . . ?
N4 C12 H12B 108.9(13) . . ?
C11 C12 H12B 110.0(13) . . ?
N4 C12 H12A 109.1(14) . . ?
C11 C12 H12A 111.4(14) . . ?
H12B C12 H12A 109.1(19) . . ?
N4 C13 C14 109.62(19) . . ?
N4 C13 H13B 108.5(15) . . ?
C14 C13 H13B 109.0(15) . . ?
N4 C13 H13A 108.1(16) . . ?
C14 C13 H13A 111.7(17) . . ?
H13B C13 H13A 110(2) . . ?
N3 C14 C13 109.5(2) . . ?
N3 C14 H14B 107.8(14) . . ?
C13 C14 H14B 109.5(14) . . ?
N3 C14 H14A 108.2(14) . . ?
C13 C14 H14A 109.0(14) . . ?
H14B C14 H14A 113(2) . . ?
C16A C15A S2 129.1(6) . . ?
C16A C15A H15A 105.0 . . ?
S2 C15A H15A 105.0 . . ?
C16A C15A H15B 105.0 . . ?
S2 C15A H15B 105.0 . . ?
H15A C15A H15B 105.9 . . ?
C15A C16A C17A 122.6(7) . . ?
C15A C16A H16A 106.7 . . ?
C17A C16A H16A 106.7 . . ?
C15A C16A H16B 106.7 . . ?
C17A C16A H16B 106.7 . . ?
H16A C16A H16B 106.6 . . ?
C16B C15B S2 131.2(8) . . ?
C16B C15B H15C 104.5 . . ?
S2 C15B H15C 104.5 . . ?
C16B C15B H15D 104.5 . . ?
S2 C15B H15D 104.5 . . ?
H15C C15B H15D 105.6 . . ?
C15B C16B C17B 129.2(11) . . ?
C15B C16B H16C 105.0 . . ?
C17B C16B H16C 105.0 . . ?
C15B C16B H16D 105.0 . . ?
C17B C16B H16D 105.0 . . ?
H16C C16B H16D 105.8 . . ?
C16B C17B H17D 109.5 . . ?
C16B C17B H17E 109.5 . . ?
H17D C17B H17E 109.5 . . ?
C16B C17B H17F 109.5 . . ?
H17D C17B H17F 109.5 . . ?
H17E C17B H17F 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 S1 C1 C6 -0.41(16) . . . . ?
C8 S1 C1 C2 177.96(19) . . . . ?
C6 C1 C2 C3 -9.7(3) . . . . ?
S1 C1 C2 C3 172.20(18) . . . . ?
C1 C2 C3 C4 42.5(3) . . . . ?
O1 S2 N4 C13 -37.8(2) . . . . ?
O2 S2 N4 C13 -165.89(19) . . . . ?
C15B S2 N4 C13 84.6(4) . . . . ?
C15A S2 N4 C13 74.6(3) . . . . ?
O1 S2 N4 C12 177.61(15) . . . . ?
O2 S2 N4 C12 49.48(18) . . . . ?
C15B S2 N4 C12 -60.0(3) . . . . ?
C15A S2 N4 C12 -70.0(3) . . . . ?
C2 C3 C4 C5 -63.5(3) . . . . ?
C3 C4 C5 C6 47.5(3) . . . . ?
C2 C1 C6 C7 -179.9(2) . . . . ?
S1 C1 C6 C7 -1.6(2) . . . . ?
C2 C1 C6 C5 -4.5(3) . . . . ?
S1 C1 C6 C5 173.78(16) . . . . ?
C4 C5 C6 C1 -14.7(3) . . . . ?
C4 C5 C6 C7 160.0(2) . . . . ?
C1 C6 C7 C8 3.5(2) . . . . ?
C5 C6 C7 C8 -171.54(19) . . . . ?
C1 C6 C7 C10 -177.7(2) . . . . ?
C5 C6 C7 C10 7.3(3) . . . . ?
C9 N1 C8 C7 -0.8(3) . . . . ?
C9 N1 C8 S1 177.21(17) . . . . ?
C10 C7 C8 N1 -4.6(3) . . . . ?
C6 C7 C8 N1 174.4(2) . . . . ?
C10 C7 C8 S1 177.18(13) . . . . ?
C6 C7 C8 S1 -3.8(2) . . . . ?
C1 S1 C8 N1 -175.89(18) . . . . ?
C1 S1 C8 C7 2.41(15) . . . . ?
C8 N1 C9 N2 4.3(4) . . . . ?
C10 N2 C9 N1 -1.6(4) . . . . ?
C9 N2 C10 N3 176.64(19) . . . . ?
C9 N2 C10 C7 -4.8(3) . . . . ?
C14 N3 C10 N2 12.6(3) . . . . ?
C11 N3 C10 N2 -118.78(19) . . . . ?
C14 N3 C10 C7 -165.97(19) . . . . ?
C11 N3 C10 C7 62.7(2) . . . . ?
C8 C7 C10 N2 7.4(3) . . . . ?
C6 C7 C10 N2 -171.4(2) . . . . ?
C8 C7 C10 N3 -174.11(17) . . . . ?
C6 C7 C10 N3 7.1(3) . . . . ?
C10 N3 C11 C12 -163.60(16) . . . . ?
C14 N3 C11 C12 62.1(2) . . . . ?
C13 N4 C12 C11 57.0(2) . . . . ?
S2 N4 C12 C11 -156.14(14) . . . . ?
N3 C11 C12 N4 -58.8(2) . . . . ?
C12 N4 C13 C14 -56.8(3) . . . . ?
S2 N4 C13 C14 156.62(17) . . . . ?
C10 N3 C14 C13 164.70(18) . . . . ?
C11 N3 C14 C13 -60.9(2) . . . . ?
N4 C13 C14 N3 57.3(3) . . . . ?
O1 S2 C15A C16A 31.3(9) . . . . ?
O2 S2 C15A C16A 163.7(7) . . . . ?
N4 S2 C15A C16A -81.1(8) . . . . ?
C15B S2 C15A C16A 129.1(17) . . . . ?
S2 C15A C16A C17A -150.5(8) . . . . ?
O1 S2 C15B C16B 2.8(10) . . . . ?
O2 S2 C15B C16B 127.1(9) . . . . ?
N4 S2 C15B C16B -118.8(9) . . . . ?
C15A S2 C15B C16B -84.9(15) . . . . ?
S2 C15B C16B C17B 141.5(16) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        27.88
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.427
_refine_diff_density_min         -0.329
_refine_diff_density_rms         0.046
####################################################################### 
# 
# 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_compound13
_database_code_depnum_ccdc_archive 'CCDC 1410921'
_audit_update_record             
;
2016-08-13 deposited with the CCDC.
2016-09-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H22 N4 O2 S2'
_chemical_formula_sum            'C20 H22 N4 O2 S2'
_chemical_formula_weight         414.54

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   I2/a
_symmetry_space_group_name_Hall  -I2ya

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

_cell_length_a                   16.3801(11)
_cell_length_b                   10.1789(7)
_cell_length_c                   24.6397(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.967(4)
_cell_angle_gamma                90.00
_cell_volume                     3907.9(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    94693
_cell_measurement_theta_min      5.229
_cell_measurement_theta_max      56.525

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.28
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1744
_exptl_absorpt_coefficient_mu    0.297
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8303
_exptl_absorpt_correction_T_max  0.9214
_exptl_absorpt_process_details   SADABs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            90862
_diffrn_reflns_av_R_equivalents  0.0493
_diffrn_reflns_av_unetI/netI     0.0187
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         1.74
_diffrn_reflns_theta_max         28.28
_reflns_number_total             4864
_reflns_number_gt                4187
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Apex2, Bruker Instrument Service v2010, 1-2'
_computing_cell_refinement       
'SAINT V7.68A (Bruker: Madison, 2009 ) in Apex2 suite'
_computing_data_reduction        
'SAINT and XPREP Version 2008/2 (Sheldrick, Bruker AXS Inc.)'
_computing_structure_solution    
'XS V2008/1 (G. M. Sheldrick, Acta Cryst. (2008). A64, 112-122)'
_computing_structure_refinement  
'XL V2008/4 (G. M. Sheldrick, Acta Cryst. (2008). A64, 112-122)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0441P)²+4.0088P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4864
_refine_ls_number_parameters     341
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0399
_refine_ls_R_factor_gt           0.0327
_refine_ls_wR_factor_ref         0.0876
_refine_ls_wR_factor_gt          0.0828
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.002
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.71921(2) -0.19399(3) 0.582846(13) 0.01504(9) Uani 1 1 d . . .
O1 O 0.37547(6) 0.26170(10) 0.21926(4) 0.0220(2) Uani 1 1 d . . .
N1 N 0.70066(8) 0.06970(12) 0.57931(5) 0.0195(2) Uani 1 1 d . . .
C1 C 0.65618(8) -0.27818(13) 0.52313(5) 0.0144(2) Uani 1 1 d . . .
S2 S 0.41202(2) 0.13214(3) 0.226332(13) 0.01586(9) Uani 1 1 d . . .
O2 O 0.46912(7) 0.09393(11) 0.19526(4) 0.0243(2) Uani 1 1 d . . .
N2 N 0.60662(8) 0.17242(12) 0.49576(5) 0.0197(2) Uani 1 1 d . . .
C2 C 0.65373(9) -0.42588(14) 0.52300(6) 0.0186(3) Uani 1 1 d . . .
H2B H 0.6284(11) -0.4545(17) 0.5517(7) 0.023(4) Uiso 1 1 d . . .
H2A H 0.7135(11) -0.4624(17) 0.5354(7) 0.025(4) Uiso 1 1 d . . .
N3 N 0.53779(7) 0.06060(11) 0.41137(5) 0.0139(2) Uani 1 1 d . . .
C3 C 0.60275(10) -0.47697(14) 0.46385(6) 0.0204(3) Uani 1 1 d . . .
H3B H 0.6379(11) -0.4708(17) 0.4383(7) 0.023(4) Uiso 1 1 d . . .
H3A H 0.5917(12) -0.5695(19) 0.4675(8) 0.029(5) Uiso 1 1 d . . .
N4 N 0.46586(7) 0.11736(11) 0.29398(5) 0.0146(2) Uani 1 1 d . . .
C4 C 0.52160(9) -0.39555(14) 0.43879(6) 0.0184(3) Uani 1 1 d . . .
H1B H 0.4866(11) -0.3951(17) 0.4654(7) 0.021(4) Uiso 1 1 d . . .
H1A H 0.4864(11) -0.4329(16) 0.4034(7) 0.019(4) Uiso 1 1 d . . .
C5 C 0.54471(9) -0.25477(13) 0.42806(6) 0.0162(3) Uani 1 1 d . . .
H5B H 0.4956(11) -0.2016(16) 0.4169(7) 0.014(4) Uiso 1 1 d . . .
H5A H 0.5679(9) -0.2544(15) 0.3954(6) 0.011(4) Uiso 1 1 d . . .
C6 C 0.60878(8) -0.19871(13) 0.48080(5) 0.0136(2) Uani 1 1 d . . .
C7 C 0.62355(8) -0.06143(12) 0.49595(5) 0.0132(2) Uani 1 1 d . . .
C8 C 0.68022(8) -0.04494(13) 0.55141(5) 0.0148(2) Uani 1 1 d . . .
C9 C 0.65997(10) 0.17164(15) 0.54943(6) 0.0226(3) Uani 1 1 d . . .
H9 H 0.6701(11) 0.2554(18) 0.5675(7) 0.022(4) Uiso 1 1 d . . .
C10 C 0.59018(8) 0.05758(13) 0.46805(5) 0.0145(2) Uani 1 1 d . . .
C11 C 0.57910(8) 0.01481(13) 0.36934(5) 0.0143(2) Uani 1 1 d . . .
H11B H 0.6098(10) -0.0631(15) 0.3821(6) 0.010(3) Uiso 1 1 d . . .
H11A H 0.6213(11) 0.0804(17) 0.3656(7) 0.020(4) Uiso 1 1 d . . .
C12 C 0.51244(8) -0.00721(13) 0.31197(5) 0.0147(2) Uani 1 1 d . . .
H12B H 0.4711(11) -0.0774(17) 0.3151(7) 0.019(4) Uiso 1 1 d . . .
H12A H 0.5411(10) -0.0297(16) 0.2841(7) 0.016(4) Uiso 1 1 d . . .
C13 C 0.42381(9) 0.16252(14) 0.33565(6) 0.0170(3) Uani 1 1 d . . .
H13B H 0.3824(11) 0.0959(17) 0.3393(7) 0.020(4) Uiso 1 1 d . . .
H13A H 0.3962(10) 0.2452(17) 0.3232(7) 0.017(4) Uiso 1 1 d . . .
C14 C 0.49224(9) 0.18438(13) 0.39258(6) 0.0165(3) Uani 1 1 d . . .
H14B H 0.4651(10) 0.2103(16) 0.4208(7) 0.019(4) Uiso 1 1 d . . .
H14A H 0.5322(11) 0.2548(18) 0.3874(7) 0.023(4) Uiso 1 1 d . . .
C15 C 0.32676(8) 0.01798(13) 0.21078(5) 0.0160(3) Uani 1 1 d . . .
C16 C 0.33827(10) -0.10746(15) 0.19178(6) 0.0219(3) Uani 1 1 d . . .
H16 H 0.3879(12) -0.1263(18) 0.1860(8) 0.028(5) Uiso 1 1 d . . .
C17 C 0.27099(11) -0.19618(15) 0.18044(7) 0.0272(3) Uani 1 1 d . . .
H17 H 0.2780(14) -0.284(2) 0.1668(9) 0.050(6) Uiso 1 1 d . . .
C18 C 0.19359(10) -0.16037(16) 0.18769(6) 0.0265(3) Uani 1 1 d . . .
H18 H 0.1465(13) -0.225(2) 0.1803(8) 0.041(6) Uiso 1 1 d . . .
C19 C 0.18290(10) -0.03563(16) 0.20739(7) 0.0249(3) Uani 1 1 d . . .
H19 H 0.1308(12) -0.011(2) 0.2121(8) 0.034(5) Uiso 1 1 d . . .
C20 C 0.24968(9) 0.05411(14) 0.21914(6) 0.0205(3) Uani 1 1 d . . .
H20 H 0.2431(12) 0.1389(19) 0.2332(8) 0.030(5) 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 C8 1.7333(14) . ?
S1 C1 1.7401(13) . ?
O1 S2 1.4365(11) . ?
N1 C9 1.3267(19) . ?
N1 C8 1.3433(17) . ?
C1 C6 1.3584(18) . ?
C1 C2 1.5040(19) . ?
S2 O2 1.4333(10) . ?
S2 N4 1.6345(11) . ?
S2 C15 1.7656(14) . ?
N2 C10 1.3385(17) . ?
N2 C9 1.3414(18) . ?
C2 C3 1.530(2) . ?
C2 H2B 0.969(18) . ?
C2 H2A 1.002(18) . ?
N3 C10 1.3959(16) . ?
N3 C14 1.4647(16) . ?
N3 C11 1.4765(16) . ?
C3 C4 1.526(2) . ?
C3 H3B 0.977(18) . ?
C3 H3A 0.97(2) . ?
N4 C13 1.4753(16) . ?
N4 C12 1.4758(16) . ?
C4 C5 1.5259(19) . ?
C4 H1B 0.996(17) . ?
C4 H1A 0.964(17) . ?
C5 C6 1.5081(17) . ?
C5 H5B 0.938(16) . ?
C5 H5A 0.990(15) . ?
C6 C7 1.4473(17) . ?
C7 C8 1.4053(17) . ?
C7 C10 1.4167(18) . ?
C9 H9 0.952(18) . ?
C11 C12 1.5127(18) . ?
C11 H11B 0.939(15) . ?
C11 H11A 0.985(17) . ?
C12 H12B 1.003(17) . ?
C12 H12A 0.972(16) . ?
C13 C14 1.5177(18) . ?
C13 H13B 0.983(17) . ?
C13 H13A 0.960(17) . ?
C14 H14B 0.970(17) . ?
C14 H14A 1.004(18) . ?
C15 C20 1.3900(19) . ?
C15 C16 1.3926(19) . ?
C16 C17 1.385(2) . ?
C16 H16 0.889(19) . ?
C17 C18 1.383(2) . ?
C17 H17 0.97(2) . ?
C18 C19 1.390(2) . ?
C18 H18 0.99(2) . ?
C19 C20 1.385(2) . ?
C19 H19 0.931(19) . ?
C20 H20 0.948(19) . ?

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
C8 S1 C1 90.71(6) . . ?
C9 N1 C8 113.09(11) . . ?
C6 C1 C2 125.81(12) . . ?
C6 C1 S1 113.92(10) . . ?
C2 C1 S1 120.17(10) . . ?
O2 S2 O1 120.03(6) . . ?
O2 S2 N4 106.50(6) . . ?
O1 S2 N4 106.37(6) . . ?
O2 S2 C15 107.96(7) . . ?
O1 S2 C15 107.80(6) . . ?
N4 S2 C15 107.62(6) . . ?
C10 N2 C9 117.71(12) . . ?
C1 C2 C3 110.37(11) . . ?
C1 C2 H2B 108.4(10) . . ?
C3 C2 H2B 111.2(10) . . ?
C1 C2 H2A 110.3(10) . . ?
C3 C2 H2A 111.0(10) . . ?
H2B C2 H2A 105.4(14) . . ?
C10 N3 C14 115.54(10) . . ?
C10 N3 C11 114.93(10) . . ?
C14 N3 C11 110.42(10) . . ?
C4 C3 C2 110.62(11) . . ?
C4 C3 H3B 108.5(10) . . ?
C2 C3 H3B 109.6(10) . . ?
C4 C3 H3A 113.6(11) . . ?
C2 C3 H3A 107.7(11) . . ?
H3B C3 H3A 106.7(15) . . ?
C13 N4 C12 111.57(10) . . ?
C13 N4 S2 117.40(9) . . ?
C12 N4 S2 116.86(9) . . ?
C5 C4 C3 110.39(11) . . ?
C5 C4 H1B 109.5(10) . . ?
C3 C4 H1B 110.0(10) . . ?
C5 C4 H1A 109.0(10) . . ?
C3 C4 H1A 110.8(10) . . ?
H1B C4 H1A 107.1(13) . . ?
C6 C5 C4 110.48(11) . . ?
C6 C5 H5B 109.9(10) . . ?
C4 C5 H5B 110.9(10) . . ?
C6 C5 H5A 111.1(9) . . ?
C4 C5 H5A 108.8(9) . . ?
H5B C5 H5A 105.6(13) . . ?
C1 C6 C7 111.49(11) . . ?
C1 C6 C5 121.16(12) . . ?
C7 C6 C5 127.16(11) . . ?
C8 C7 C10 114.20(11) . . ?
C8 C7 C6 111.95(11) . . ?
C10 C7 C6 133.76(12) . . ?
N1 C8 C7 125.95(12) . . ?
N1 C8 S1 122.17(10) . . ?
C7 C8 S1 111.82(10) . . ?
N1 C9 N2 127.93(13) . . ?
N1 C9 H9 117.1(10) . . ?
N2 C9 H9 114.9(10) . . ?
N2 C10 N3 117.13(12) . . ?
N2 C10 C7 120.83(12) . . ?
N3 C10 C7 122.03(11) . . ?
N3 C11 C12 110.32(10) . . ?
N3 C11 H11B 110.2(9) . . ?
C12 C11 H11B 110.2(9) . . ?
N3 C11 H11A 109.7(10) . . ?
C12 C11 H11A 109.8(10) . . ?
H11B C11 H11A 106.6(13) . . ?
N4 C12 C11 108.10(10) . . ?
N4 C12 H12B 109.7(9) . . ?
C11 C12 H12B 110.1(9) . . ?
N4 C12 H12A 107.9(10) . . ?
C11 C12 H12A 109.2(9) . . ?
H12B C12 H12A 111.8(13) . . ?
N4 C13 C14 108.59(11) . . ?
N4 C13 H13B 109.4(10) . . ?
C14 C13 H13B 110.5(10) . . ?
N4 C13 H13A 109.0(9) . . ?
C14 C13 H13A 107.9(10) . . ?
H13B C13 H13A 111.3(14) . . ?
N3 C14 C13 108.96(11) . . ?
N3 C14 H14B 108.0(10) . . ?
C13 C14 H14B 109.3(10) . . ?
N3 C14 H14A 111.5(10) . . ?
C13 C14 H14A 108.2(10) . . ?
H14B C14 H14A 110.9(14) . . ?
C20 C15 C16 121.05(13) . . ?
C20 C15 S2 119.18(11) . . ?
C16 C15 S2 119.76(11) . . ?
C17 C16 C15 118.94(14) . . ?
C17 C16 H16 122.5(12) . . ?
C15 C16 H16 118.5(12) . . ?
C18 C17 C16 120.42(14) . . ?
C18 C17 H17 119.8(13) . . ?
C16 C17 H17 119.8(13) . . ?
C17 C18 C19 120.36(14) . . ?
C17 C18 H18 119.8(12) . . ?
C19 C18 H18 119.8(12) . . ?
C20 C19 C18 119.93(15) . . ?
C20 C19 H19 119.2(12) . . ?
C18 C19 H19 120.8(12) . . ?
C19 C20 C15 119.29(14) . . ?
C19 C20 H20 120.3(11) . . ?
C15 C20 H20 120.4(11) . . ?

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 S1 C1 C6 1.01(10) . . . . ?
C8 S1 C1 C2 -175.55(11) . . . . ?
C6 C1 C2 C3 10.54(19) . . . . ?
S1 C1 C2 C3 -173.33(9) . . . . ?
C1 C2 C3 C4 -42.65(15) . . . . ?
O2 S2 N4 C13 174.55(10) . . . . ?
O1 S2 N4 C13 45.43(11) . . . . ?
C15 S2 N4 C13 -69.89(11) . . . . ?
O2 S2 N4 C12 -48.83(11) . . . . ?
O1 S2 N4 C12 -177.96(9) . . . . ?
C15 S2 N4 C12 66.72(10) . . . . ?
C2 C3 C4 C5 65.17(15) . . . . ?
C3 C4 C5 C6 -50.98(15) . . . . ?
C2 C1 C6 C7 177.00(12) . . . . ?
S1 C1 C6 C7 0.67(14) . . . . ?
C2 C1 C6 C5 1.7(2) . . . . ?
S1 C1 C6 C5 -174.62(9) . . . . ?
C4 C5 C6 C1 18.64(17) . . . . ?
C4 C5 C6 C7 -155.86(12) . . . . ?
C1 C6 C7 C8 -2.52(15) . . . . ?
C5 C6 C7 C8 172.42(12) . . . . ?
C1 C6 C7 C10 -178.96(13) . . . . ?
C5 C6 C7 C10 -4.0(2) . . . . ?
C9 N1 C8 C7 1.2(2) . . . . ?
C9 N1 C8 S1 -175.72(11) . . . . ?
C10 C7 C8 N1 3.21(19) . . . . ?
C6 C7 C8 N1 -173.97(12) . . . . ?
C10 C7 C8 S1 -179.55(9) . . . . ?
C6 C7 C8 S1 3.27(14) . . . . ?
C1 S1 C8 N1 174.91(12) . . . . ?
C1 S1 C8 C7 -2.45(10) . . . . ?
C8 N1 C9 N2 -3.6(2) . . . . ?
C10 N2 C9 N1 1.0(2) . . . . ?
C9 N2 C10 N3 -177.08(12) . . . . ?
C9 N2 C10 C7 4.16(19) . . . . ?
C14 N3 C10 N2 -12.53(17) . . . . ?
C11 N3 C10 N2 117.90(13) . . . . ?
C14 N3 C10 C7 166.22(12) . . . . ?
C11 N3 C10 C7 -63.35(16) . . . . ?
C8 C7 C10 N2 -5.93(18) . . . . ?
C6 C7 C10 N2 170.45(13) . . . . ?
C8 C7 C10 N3 175.37(11) . . . . ?
C6 C7 C10 N3 -8.3(2) . . . . ?
C10 N3 C11 C12 167.13(11) . . . . ?
C14 N3 C11 C12 -60.00(14) . . . . ?
C13 N4 C12 C11 -59.14(13) . . . . ?
S2 N4 C12 C11 161.84(9) . . . . ?
N3 C11 C12 N4 57.82(13) . . . . ?
C12 N4 C13 C14 60.43(14) . . . . ?
S2 N4 C13 C14 -160.79(9) . . . . ?
C10 N3 C14 C13 -167.23(11) . . . . ?
C11 N3 C14 C13 60.21(14) . . . . ?
N4 C13 C14 N3 -59.62(14) . . . . ?
O2 S2 C15 C20 -158.52(11) . . . . ?
O1 S2 C15 C20 -27.47(13) . . . . ?
N4 S2 C15 C20 86.89(12) . . . . ?
O2 S2 C15 C16 23.08(13) . . . . ?
O1 S2 C15 C16 154.13(11) . . . . ?
N4 S2 C15 C16 -91.51(12) . . . . ?
C20 C15 C16 C17 0.9(2) . . . . ?
S2 C15 C16 C17 179.24(11) . . . . ?
C15 C16 C17 C18 0.3(2) . . . . ?
C16 C17 C18 C19 -1.1(2) . . . . ?
C17 C18 C19 C20 0.9(2) . . . . ?
C18 C19 C20 C15 0.2(2) . . . . ?
C16 C15 C20 C19 -1.1(2) . . . . ?
S2 C15 C20 C19 -179.50(11) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        28.28
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.349
_refine_diff_density_min         -0.474
_refine_diff_density_rms         0.061
