# 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).
# 
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# 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 
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data_3d_0m
_database_code_depnum_ccdc_archive 'CCDC 1430747'
_audit_update_record             
;
2015-10-12 deposited with the CCDC.
2016-08-08 downloaded from the CCDC.
;
_audit_creation_date             2015-10-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H16 N4 S2'
_chemical_formula_sum            'C23 H16 N4 S2'
_chemical_formula_weight         412.52
_chemical_melting_point          ?
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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   11.0027(13)
_cell_length_b                   9.2037(10)
_cell_length_c                   20.727(3)
_cell_angle_alpha                90
_cell_angle_beta                 104.570(4)
_cell_angle_gamma                90
_cell_volume                     2031.4(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1648
_cell_measurement_temperature    298
_cell_measurement_theta_max      21.19
_cell_measurement_theta_min      2.93
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.279
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7067
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0863 before and 0.0515 after correction.
The Ratio of minimum to maximum transmission is 0.9478.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'metallic light colourless'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0701
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            71435
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.511
_diffrn_reflns_theta_min         2.030
_diffrn_ambient_temperature      298
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3476
_reflns_number_total             4657
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.604
_refine_diff_density_min         -0.508
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         4657
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0895
_refine_ls_R_factor_gt           0.0657
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1094P)²+1.6995P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1986
_refine_ls_wR_factor_ref         0.2125
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C8(H8), C9(H9), C10(H10),
 C11(H11), C17(H17), C18(H18), C19(H19), C21(H21), C22(H22), C23(H23)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.77573(9) -0.27226(11) 0.07859(5) 0.0696(3) Uani 1 1 d . . . . .
S2 S 0.67648(12) -0.34517(12) 0.46130(5) 0.0809(4) Uani 1 1 d . . . . .
N1 N 0.4333(2) 0.2325(2) 0.23043(11) 0.0384(5) Uani 1 1 d . . . . .
N2 N 0.5352(2) 0.0523(2) 0.18663(11) 0.0390(5) Uani 1 1 d . . . . .
N3 N 0.6282(2) -0.1435(2) 0.25699(12) 0.0435(5) Uani 1 1 d . . . . .
N4 N 0.5092(2) 0.0352(2) 0.29747(11) 0.0388(5) Uani 1 1 d . . . . .
C1 C 0.5326(3) 0.3746(4) 0.15778(16) 0.0558(8) Uani 1 1 d . . . . .
H1 H 0.6114 0.3489 0.1839 0.067 Uiso 1 1 calc R . . . .
C2 C 0.5218(4) 0.4668(4) 0.10371(19) 0.0689(10) Uani 1 1 d . . . . .
H2 H 0.5938 0.5023 0.0935 0.083 Uiso 1 1 calc R . . . .
C3 C 0.4065(4) 0.5059(4) 0.06538(17) 0.0655(10) Uani 1 1 d . . . . .
H3 H 0.4001 0.5682 0.0294 0.079 Uiso 1 1 calc R . . . .
C4 C 0.3004(4) 0.4531(4) 0.08012(16) 0.0634(9) Uani 1 1 d . . . . .
H4 H 0.2219 0.4798 0.0540 0.076 Uiso 1 1 calc R . . . .
C5 C 0.3090(3) 0.3600(3) 0.13379(14) 0.0485(7) Uani 1 1 d . . . . .
H5 H 0.2367 0.3240 0.1436 0.058 Uiso 1 1 calc R . . . .
C6 C 0.4257(3) 0.3215(3) 0.17243(13) 0.0387(5) Uani 1 1 d . . . . .
C7 C 0.4242(3) 0.4192(4) 0.31167(17) 0.0575(8) Uani 1 1 d . . . . .
H7 H 0.4952 0.4614 0.3029 0.069 Uiso 1 1 calc R . . . .
C8 C 0.3661(4) 0.4846(5) 0.35628(18) 0.0735(11) Uani 1 1 d . . . . .
H8 H 0.3981 0.5705 0.3775 0.088 Uiso 1 1 calc R . . . .
C9 C 0.2614(4) 0.4224(5) 0.36904(17) 0.0729(12) Uani 1 1 d . . . . .
H9 H 0.2219 0.4670 0.3985 0.087 Uiso 1 1 calc R . . . .
C10 C 0.2150(4) 0.2954(5) 0.3387(2) 0.0738(12) Uani 1 1 d . . . . .
H10 H 0.1440 0.2537 0.3478 0.089 Uiso 1 1 calc R . . . .
C11 C 0.2733(3) 0.2273(4) 0.29414(17) 0.0559(8) Uani 1 1 d . . . . .
H11 H 0.2426 0.1398 0.2741 0.067 Uiso 1 1 calc R . . . .
C12 C 0.3769(2) 0.2915(3) 0.28027(13) 0.0389(6) Uani 1 1 d . . . . .
C13 C 0.4934(2) 0.1020(3) 0.23817(12) 0.0358(5) Uani 1 1 d . . . . .
C14 C 0.5771(2) -0.0867(3) 0.30367(13) 0.0378(5) Uani 1 1 d . . . . .
C15 C 0.6007(2) -0.0709(3) 0.19909(13) 0.0384(5) Uani 1 1 d . . . . .
C16 C 0.5974(3) -0.1635(3) 0.36758(13) 0.0420(6) Uani 1 1 d . . . . .
C17 C 0.5416(3) -0.1231(3) 0.41956(14) 0.0487(7) Uani 1 1 d . . . . .
H17 H 0.4896 -0.0427 0.4172 0.058 Uiso 1 1 calc R . . . .
C18 C 0.5733(3) -0.2188(3) 0.47669(13) 0.0444(6) Uani 1 1 d . . . . .
H18 H 0.5431 -0.2128 0.5147 0.053 Uiso 1 1 calc R . . . .
C19 C 0.6715(3) -0.2844(4) 0.38387(16) 0.0581(8) Uani 1 1 d . . . . .
H19 H 0.7141 -0.3279 0.3555 0.070 Uiso 1 1 calc R . . . .
C20 C 0.6463(3) -0.1306(3) 0.14385(14) 0.0417(6) Uani 1 1 d . . . . .
C21 C 0.5931(3) -0.1001(4) 0.07574(16) 0.0570(8) Uani 1 1 d . . . . .
H21 H 0.5255 -0.0375 0.0608 0.068 Uiso 1 1 calc R . . . .
C22 C 0.6539(3) -0.1754(3) 0.03218(15) 0.0494(7) Uani 1 1 d . . . . .
H22 H 0.6303 -0.1718 -0.0141 0.059 Uiso 1 1 calc R . . . .
C23 C 0.7462(3) -0.2246(4) 0.15160(17) 0.0559(8) Uani 1 1 d . . . . .
H23 H 0.7925 -0.2582 0.1928 0.067 Uiso 1 1 calc R . . . .


_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 C22 1.694(3) . ?
S1 C23 1.684(3) . ?
S2 C18 1.710(3) . ?
S2 C19 1.688(3) . ?
N1 C6 1.440(3) . ?
N1 C12 1.439(3) . ?
N1 C13 1.361(3) . ?
N2 C13 1.345(3) . ?
N2 C15 1.333(3) . ?
N3 C14 1.341(3) . ?
N3 C15 1.340(3) . ?
N4 C13 1.346(3) . ?
N4 C14 1.336(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.387(5) . ?
C1 C6 1.376(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.365(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.368(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.388(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.378(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.387(5) . ?
C7 C12 1.380(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.369(6) . ?
C9 H9 0.9300 . ?
C9 C10 1.365(6) . ?
C10 H10 0.9300 . ?
C10 C11 1.399(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.376(4) . ?
C14 C16 1.468(4) . ?
C15 C20 1.468(4) . ?
C16 C17 1.417(4) . ?
C16 C19 1.371(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.446(4) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 C21 1.414(4) . ?
C20 C23 1.376(4) . ?
C21 H21 0.9300 . ?
C21 C22 1.431(4) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?

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
C23 S1 C22 93.98(15) . . ?
C19 S2 C18 95.04(15) . . ?
C12 N1 C6 116.11(19) . . ?
C13 N1 C6 121.6(2) . . ?
C13 N1 C12 122.2(2) . . ?
C15 N2 C13 114.3(2) . . ?
C15 N3 C14 114.2(2) . . ?
C14 N4 C13 114.3(2) . . ?
C2 C1 H1 120.3 . . ?
C6 C1 H1 120.3 . . ?
C6 C1 C2 119.4(3) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 C1 120.7(3) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 H3 120.1 . . ?
C2 C3 C4 119.8(3) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 119.7 . . ?
C3 C4 C5 120.6(3) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 H5 120.3 . . ?
C6 C5 C4 119.3(3) . . ?
C6 C5 H5 120.3 . . ?
C1 C6 N1 120.9(3) . . ?
C1 C6 C5 120.2(3) . . ?
C5 C6 N1 118.8(2) . . ?
C8 C7 H7 120.0 . . ?
C12 C7 H7 120.0 . . ?
C12 C7 C8 120.1(3) . . ?
C7 C8 H8 120.0 . . ?
C9 C8 C7 119.9(4) . . ?
C9 C8 H8 120.0 . . ?
C8 C9 H9 119.8 . . ?
C10 C9 C8 120.3(3) . . ?
C10 C9 H9 119.8 . . ?
C9 C10 H10 119.8 . . ?
C9 C10 C11 120.4(4) . . ?
C11 C10 H10 119.8 . . ?
C10 C11 H11 120.4 . . ?
C12 C11 C10 119.2(3) . . ?
C12 C11 H11 120.4 . . ?
C7 C12 N1 118.7(3) . . ?
C11 C12 N1 121.1(3) . . ?
C11 C12 C7 120.1(3) . . ?
N2 C13 N1 117.4(2) . . ?
N2 C13 N4 125.4(2) . . ?
N4 C13 N1 117.2(2) . . ?
N3 C14 C16 117.8(2) . . ?
N4 C14 N3 125.7(2) . . ?
N4 C14 C16 116.5(2) . . ?
N2 C15 N3 125.9(2) . . ?
N2 C15 C20 116.2(2) . . ?
N3 C15 C20 117.9(2) . . ?
C17 C16 C14 124.3(2) . . ?
C19 C16 C14 124.0(3) . . ?
C19 C16 C17 111.7(3) . . ?
C16 C17 H17 123.2 . . ?
C16 C17 C18 113.7(3) . . ?
C18 C17 H17 123.2 . . ?
S2 C18 H18 126.4 . . ?
C17 C18 S2 107.2(2) . . ?
C17 C18 H18 126.4 . . ?
S2 C19 H19 123.9 . . ?
C16 C19 S2 112.2(3) . . ?
C16 C19 H19 123.9 . . ?
C21 C20 C15 124.6(2) . . ?
C23 C20 C15 124.3(3) . . ?
C23 C20 C21 111.1(3) . . ?
C20 C21 H21 123.5 . . ?
C20 C21 C22 113.1(3) . . ?
C22 C21 H21 123.5 . . ?
S1 C22 H22 125.5 . . ?
C21 C22 S1 109.0(2) . . ?
C21 C22 H22 125.5 . . ?
S1 C23 H23 123.6 . . ?
C20 C23 S1 112.8(2) . . ?
C20 C23 H23 123.6 . . ?

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
N2 C15 C20 C21 -22.8(4) . . . . ?
N2 C15 C20 C23 157.6(3) . . . . ?
N3 C14 C16 C17 -174.9(3) . . . . ?
N3 C14 C16 C19 4.1(4) . . . . ?
N3 C15 C20 C21 157.3(3) . . . . ?
N3 C15 C20 C23 -22.3(4) . . . . ?
N4 C14 C16 C17 5.4(4) . . . . ?
N4 C14 C16 C19 -175.5(3) . . . . ?
C1 C2 C3 C4 -0.4(6) . . . . ?
C2 C1 C6 N1 -176.3(3) . . . . ?
C2 C1 C6 C5 -0.2(5) . . . . ?
C2 C3 C4 C5 0.0(5) . . . . ?
C3 C4 C5 C6 0.2(5) . . . . ?
C4 C5 C6 N1 176.0(3) . . . . ?
C4 C5 C6 C1 -0.1(4) . . . . ?
C6 N1 C12 C7 -62.3(3) . . . . ?
C6 N1 C12 C11 114.1(3) . . . . ?
C6 N1 C13 N2 -6.4(4) . . . . ?
C6 N1 C13 N4 171.9(2) . . . . ?
C6 C1 C2 C3 0.5(5) . . . . ?
C7 C8 C9 C10 0.8(6) . . . . ?
C8 C7 C12 N1 175.2(3) . . . . ?
C8 C7 C12 C11 -1.3(5) . . . . ?
C8 C9 C10 C11 -0.2(6) . . . . ?
C9 C10 C11 C12 -1.2(5) . . . . ?
C10 C11 C12 N1 -174.5(3) . . . . ?
C10 C11 C12 C7 1.9(5) . . . . ?
C12 N1 C6 C1 116.6(3) . . . . ?
C12 N1 C6 C5 -59.5(3) . . . . ?
C12 N1 C13 N2 175.5(2) . . . . ?
C12 N1 C13 N4 -6.3(4) . . . . ?
C12 C7 C8 C9 -0.1(5) . . . . ?
C13 N1 C6 C1 -61.7(4) . . . . ?
C13 N1 C6 C5 122.2(3) . . . . ?
C13 N1 C12 C7 115.9(3) . . . . ?
C13 N1 C12 C11 -67.6(3) . . . . ?
C13 N2 C15 N3 -1.2(4) . . . . ?
C13 N2 C15 C20 179.0(2) . . . . ?
C13 N4 C14 N3 0.2(4) . . . . ?
C13 N4 C14 C16 179.8(2) . . . . ?
C14 N3 C15 N2 3.8(4) . . . . ?
C14 N3 C15 C20 -176.3(2) . . . . ?
C14 N4 C13 N1 -175.1(2) . . . . ?
C14 N4 C13 N2 3.0(4) . . . . ?
C14 C16 C17 C18 178.1(2) . . . . ?
C14 C16 C19 S2 179.3(2) . . . . ?
C15 N2 C13 N1 175.6(2) . . . . ?
C15 N2 C13 N4 -2.5(4) . . . . ?
C15 N3 C14 N4 -3.3(4) . . . . ?
C15 N3 C14 C16 177.1(2) . . . . ?
C15 C20 C21 C22 -178.6(3) . . . . ?
C15 C20 C23 S1 -179.6(2) . . . . ?
C16 C17 C18 S2 3.0(3) . . . . ?
C17 C16 C19 S2 -1.5(4) . . . . ?
C18 S2 C19 C16 2.9(3) . . . . ?
C19 S2 C18 C17 -3.2(2) . . . . ?
C19 C16 C17 C18 -1.0(4) . . . . ?
C20 C21 C22 S1 -2.4(4) . . . . ?
C21 C20 C23 S1 0.8(4) . . . . ?
C22 S1 C23 C20 -1.9(3) . . . . ?
C23 S1 C22 C21 2.4(3) . . . . ?
C23 C20 C21 C22 1.1(4) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_w
_database_code_depnum_ccdc_archive 'CCDC 1430748'
_audit_update_record             
;
2015-10-12 deposited with the CCDC.
2016-08-08 downloaded from the CCDC.
;
_audit_creation_date             2015-10-07
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H16 N4 S2'
_chemical_formula_sum            'C23 H16 N4 S2'
_chemical_formula_weight         412.52
_chemical_melting_point          ?
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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   11.0590(6)
_cell_length_b                   9.0657(5)
_cell_length_c                   20.5704(11)
_cell_angle_alpha                90
_cell_angle_beta                 103.800(2)
_cell_angle_gamma                90
_cell_volume                     2002.81(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9682
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.53
_cell_measurement_theta_min      2.47
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.283
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.4
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_av_unetI/netI     0.0125
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            54220
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.559
_diffrn_reflns_theta_min         2.358
_diffrn_ambient_temperature      100.01
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'CCD Area Detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4174
_reflns_number_total             4622
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.336
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.078
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     300
_refine_ls_number_reflns         4622
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.0357
_refine_ls_R_factor_gt           0.0311
_refine_ls_restrained_S_all      1.096
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0475P)²+0.6746P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0860
_refine_ls_wR_factor_ref         0.0892
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained planarity
 S0AA, S0AB, C00F, C00R, C00S, C1, C1A
 with sigma of 0.1
3. Rigid bond restraints
 S0AA, S0AB, C00F, C1, C1A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
4. Others
 Sof(S0)=Sof(C0)=Sof(H0)=Sof(H00A)=Sof(H00D)=1-FVAR(1)
 Sof(S002)=Sof(H00Q)=Sof(H00T)=Sof(C003)=Sof(H003)=FVAR(1)
 Sof(S0AB)=Sof(H00B)=Sof(H00C)=Sof(C1A)=Sof(H1A)=1-FVAR(2)
 Sof(S0AA)=Sof(H00R)=Sof(H00S)=Sof(C1)=Sof(H1)=FVAR(2)
5.a Aromatic/amide H refined with riding coordinates:
 C0(H0), C00E(H00E), C00H(H00H), C00I(H00I), C00J(H00J), C00K(H00K),
 C00L(H00L), C00M(H00M), C00N(H00N), C00O(H00O), C00P(H00P), C00Q(H00Q),
 C00Q(H00A), C00R(H00R), C00R(H00B), C00S(H00S), C00S(H00C), C00T(H00T),
 C00T(H00D), C1(H1), C1A(H1A), C003(H003)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
S0 S 0.76390(18) 0.2477(2) 0.16139(9) 0.0220(3) Uani 0.485(2) 1 d . . P A 2
S0AA S 0.52281(7) 0.39616(8) 0.43289(3) 0.01712(13) Uani 0.822(2) 1 d . U P B 1
S0AB S 0.6804(5) 0.1870(5) 0.3866(3) 0.0221(7) Uani 0.178(2) 1 d . U P B 2
S002 S 0.57647(18) 0.4218(2) 0.06915(8) 0.0212(3) Uani 0.515(2) 1 d . . P A 1
N004 N 0.53217(9) 0.55260(10) 0.19033(5) 0.01655(19) Uani 1 1 d . . . . .
N005 N 0.50371(8) 0.53616(10) 0.30172(5) 0.01638(19) Uani 1 1 d . . . . .
N006 N 0.62621(9) 0.35540(11) 0.26165(5) 0.0180(2) Uani 1 1 d . . . . .
N008 N 0.43228(9) 0.73778(10) 0.23376(5) 0.01616(19) Uani 1 1 d . . . . .
C0 C 0.6015(7) 0.3939(9) 0.0789(4) 0.035(2) Uani 0.485(2) 1 d . . P A 2
H0 H 0.5348 0.4590 0.0606 0.042 Uiso 0.485(2) 1 calc R . P A 2
C00A C 0.49028(10) 0.60463(12) 0.24220(5) 0.0155(2) Uani 1 1 d . . . . .
C00B C 0.59857(10) 0.42875(12) 0.20327(6) 0.0163(2) Uani 1 1 d . . . . .
C00C C 0.37565(10) 0.80163(12) 0.28349(5) 0.0158(2) Uani 1 1 d . . . . .
C00D C 0.43020(10) 0.82742(12) 0.17568(5) 0.0161(2) Uani 1 1 d . . . . .
C00E C 0.27074(11) 0.73832(13) 0.29757(6) 0.0204(2) Uani 1 1 d . . . . .
H00E H 0.2400 0.6467 0.2780 0.024 Uiso 1 1 calc R . . . .
C00F C 0.59264(10) 0.33578(12) 0.37182(5) 0.0175(2) Uani 1 1 d . U . . .
C00G C 0.64400(10) 0.36797(12) 0.14770(6) 0.0176(2) Uani 1 1 d . . . . .
C00H C 0.31630(11) 0.87923(13) 0.13884(6) 0.0193(2) Uani 1 1 d . . . . .
H00H H 0.2414 0.8508 0.1503 0.023 Uiso 1 1 calc R . . . .
C00I C 0.21091(11) 0.81051(14) 0.34073(6) 0.0239(3) Uani 1 1 d . . . . .
H00I H 0.1388 0.7681 0.3506 0.029 Uiso 1 1 calc R . . . .
C00J C 0.42294(11) 0.93380(13) 0.31311(6) 0.0211(2) Uani 1 1 d . . . . .
H00J H 0.4958 0.9755 0.3038 0.025 Uiso 1 1 calc R . . . .
C00K C 0.25602(12) 0.94410(14) 0.36944(6) 0.0242(3) Uani 1 1 d . . . . .
H00K H 0.2136 0.9941 0.3980 0.029 Uiso 1 1 calc R . . . .
C00L C 0.54001(11) 0.86812(14) 0.15906(6) 0.0221(2) Uani 1 1 d . . . . .
H00L H 0.6178 0.8331 0.1847 0.027 Uiso 1 1 calc R . . . .
C00M C 0.31285(12) 0.97303(13) 0.08497(6) 0.0241(3) Uani 1 1 d . . . . .
H00M H 0.2352 1.0093 0.0597 0.029 Uiso 1 1 calc R . . . .
C00N C 0.53502(12) 0.96040(14) 0.10471(6) 0.0262(3) Uani 1 1 d . . . . .
H00N H 0.6098 0.9872 0.0926 0.031 Uiso 1 1 calc R . . . .
C00O C 0.42202(13) 1.01391(13) 0.06787(6) 0.0256(3) Uani 1 1 d . . . . .
H00O H 0.4194 1.0783 0.0311 0.031 Uiso 1 1 calc R . . . .
C00P C 0.36269(12) 1.00463(14) 0.35646(6) 0.0247(3) Uani 1 1 d . . . . .
H00P H 0.3948 1.0947 0.3772 0.030 Uiso 1 1 calc R . . . .
C00Q C 0.66872(13) 0.31235(14) 0.03813(6) 0.0272(3) Uani 1 1 d . . . . .
H00Q H 0.6599 0.3044 -0.0088 0.033 Uiso 0.515(2) 1 calc R . P A 1
H00A H 0.6539 0.3133 -0.0093 0.033 Uiso 0.485(2) 1 calc R . P A 2
C00R C 0.58644(12) 0.25812(14) 0.48480(6) 0.0251(3) Uani 1 1 d . . . . .
H00R H 0.5724 0.2457 0.5283 0.030 Uiso 0.822(2) 1 calc R . P B 1
H00B H 0.5670 0.2560 0.5273 0.030 Uiso 0.178(2) 1 calc R . P B 2
C00S C 0.65961(13) 0.16642(14) 0.45863(7) 0.0294(3) Uani 1 1 d . . . . .
H00S H 0.7026 0.0833 0.4811 0.035 Uiso 0.822(2) 1 calc R . P B 1
H00C H 0.6998 0.0866 0.4851 0.035 Uiso 0.178(2) 1 calc R . P B 2
C00T C 0.75671(13) 0.23474(14) 0.08136(7) 0.0296(3) Uani 1 1 d . . . . .
H00T H 0.8178 0.1717 0.0706 0.036 Uiso 0.515(2) 1 calc R . P A 1
H00D H 0.8134 0.1737 0.0656 0.036 Uiso 0.485(2) 1 calc R . P A 2
C1 C 0.6631(5) 0.2123(5) 0.3924(3) 0.0271(7) Uani 0.822(2) 1 d . U P B 1
H1 H 0.7093 0.1625 0.3656 0.033 Uiso 0.822(2) 1 calc R . P B 1
C1A C 0.5413(18) 0.3728(19) 0.4227(8) 0.032(3) Uani 0.178(2) 1 d . U P B 2
H1A H 0.4868 0.4539 0.4225 0.038 Uiso 0.178(2) 1 calc R . P B 2
C003 C 0.7391(7) 0.2674(10) 0.1481(4) 0.039(2) Uani 0.515(2) 1 d . . P A 1
H003 H 0.7878 0.2241 0.1878 0.046 Uiso 0.515(2) 1 calc R . P A 1
C009 C 0.57265(10) 0.41372(12) 0.30791(5) 0.0161(2) 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
S0 C00G 1.687(2) . ?
S0 C00T 1.633(2) . ?
S0AA C00F 1.7138(12) . ?
S0AA C00R 1.6861(13) . ?
S0AB C00F 1.647(3) . ?
S0AB C00S 1.565(5) . ?
S002 C00G 1.683(2) . ?
S002 C00Q 1.656(2) . ?
N004 C00A 1.3458(14) . ?
N004 C00B 1.3332(14) . ?
N005 C00A 1.3489(14) . ?
N005 C009 1.3354(14) . ?
N006 C00B 1.3425(15) . ?
N006 C009 1.3434(15) . ?
N008 C00A 1.3586(14) . ?
N008 C00C 1.4421(14) . ?
N008 C00D 1.4405(14) . ?
C0 H0 0.9500 . ?
C0 C00G 1.400(8) . ?
C0 C00Q 1.449(8) . ?
C00B C00G 1.4618(15) . ?
C00C C00E 1.3855(16) . ?
C00C C00J 1.3886(16) . ?
C00D C00H 1.3879(16) . ?
C00D C00L 1.3878(16) . ?
C00E H00E 0.9500 . ?
C00E C00I 1.3908(17) . ?
C00F C1 1.372(4) . ?
C00F C1A 1.347(13) . ?
C00F C009 1.4621(15) . ?
C00G C003 1.390(8) . ?
C00H H00H 0.9500 . ?
C00H C00M 1.3901(16) . ?
C00I H00I 0.9500 . ?
C00I C00K 1.3870(19) . ?
C00J H00J 0.9500 . ?
C00J C00P 1.3911(16) . ?
C00K H00K 0.9500 . ?
C00K C00P 1.3836(19) . ?
C00L H00L 0.9500 . ?
C00L C00N 1.3868(17) . ?
C00M H00M 0.9500 . ?
C00M C00O 1.3861(18) . ?
C00N H00N 0.9500 . ?
C00N C00O 1.3855(19) . ?
C00O H00O 0.9500 . ?
C00P H00P 0.9500 . ?
C00Q H00Q 0.9500 . ?
C00Q H00A 0.9500 . ?
C00Q C00T 1.349(2) . ?
C00R H00R 0.9500 . ?
C00R H00B 0.9500 . ?
C00R C00S 1.3577(19) . ?
C00R C1A 1.630(16) . ?
C00S H00S 0.9500 . ?
C00S H00C 0.9500 . ?
C00S C1 1.433(5) . ?
C00T H00T 0.9500 . ?
C00T H00D 0.9500 . ?
C00T C003 1.461(8) . ?
C1 H1 0.9500 . ?
C1A H1A 0.9500 . ?
C003 H003 0.9500 . ?

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
C00T S0 C00G 91.78(12) . . ?
C00R S0AA C00F 91.96(6) . . ?
C00S S0AB C00F 93.4(2) . . ?
C00Q S002 C00G 91.34(11) . . ?
C00B N004 C00A 114.47(9) . . ?
C009 N005 C00A 113.94(9) . . ?
C00B N006 C009 113.20(9) . . ?
C00A N008 C00C 122.53(9) . . ?
C00A N008 C00D 121.39(9) . . ?
C00D N008 C00C 115.99(8) . . ?
C00G C0 H0 123.1 . . ?
C00G C0 C00Q 113.9(4) . . ?
C00Q C0 H0 123.1 . . ?
N004 C00A N005 125.04(10) . . ?
N004 C00A N008 116.83(10) . . ?
N005 C00A N008 118.12(10) . . ?
N004 C00B N006 126.35(10) . . ?
N004 C00B C00G 115.91(10) . . ?
N006 C00B C00G 117.73(10) . . ?
C00E C00C N008 120.59(10) . . ?
C00E C00C C00J 120.82(10) . . ?
C00J C00C N008 118.41(10) . . ?
C00H C00D N008 118.47(10) . . ?
C00L C00D N008 120.84(10) . . ?
C00L C00D C00H 120.60(10) . . ?
C00C C00E H00E 120.4 . . ?
C00C C00E C00I 119.21(11) . . ?
C00I C00E H00E 120.4 . . ?
C1 C00F S0AA 110.9(2) . . ?
C1 C00F C009 128.7(2) . . ?
C1A C00F S0AB 113.6(7) . . ?
C1A C00F C009 125.3(7) . . ?
C009 C00F S0AA 120.45(9) . . ?
C009 C00F S0AB 121.16(19) . . ?
C0 C00G S0 109.8(3) . . ?
C0 C00G C00B 129.2(3) . . ?
C00B C00G S0 121.06(10) . . ?
C00B C00G S002 119.02(10) . . ?
C003 C00G S002 110.9(3) . . ?
C003 C00G C00B 130.1(3) . . ?
C00D C00H H00H 120.3 . . ?
C00D C00H C00M 119.41(11) . . ?
C00M C00H H00H 120.3 . . ?
C00E C00I H00I 119.8 . . ?
C00K C00I C00E 120.34(11) . . ?
C00K C00I H00I 119.8 . . ?
C00C C00J H00J 120.3 . . ?
C00C C00J C00P 119.46(11) . . ?
C00P C00J H00J 120.3 . . ?
C00I C00K H00K 120.0 . . ?
C00P C00K C00I 120.05(11) . . ?
C00P C00K H00K 120.0 . . ?
C00D C00L H00L 120.3 . . ?
C00N C00L C00D 119.35(11) . . ?
C00N C00L H00L 120.3 . . ?
C00H C00M H00M 119.8 . . ?
C00O C00M C00H 120.39(12) . . ?
C00O C00M H00M 119.8 . . ?
C00L C00N H00N 119.7 . . ?
C00O C00N C00L 120.62(11) . . ?
C00O C00N H00N 119.7 . . ?
C00M C00O H00O 120.2 . . ?
C00N C00O C00M 119.62(11) . . ?
C00N C00O H00O 120.2 . . ?
C00J C00P H00P 120.0 . . ?
C00K C00P C00J 120.09(11) . . ?
C00K C00P H00P 120.0 . . ?
S002 C00Q H00Q 120.9 . . ?
C0 C00Q H00A 127.1 . . ?
C00T C00Q S002 118.17(12) . . ?
C00T C00Q C0 105.9(3) . . ?
C00T C00Q H00Q 120.9 . . ?
C00T C00Q H00A 127.1 . . ?
S0AA C00R H00R 123.2 . . ?
C00S C00R S0AA 113.68(10) . . ?
C00S C00R H00R 123.2 . . ?
C00S C00R H00B 129.8 . . ?
C00S C00R C1A 100.4(5) . . ?
C1A C00R H00B 129.8 . . ?
S0AB C00S H00C 118.7 . . ?
C00R C00S S0AB 122.60(15) . . ?
C00R C00S H00S 124.7 . . ?
C00R C00S H00C 118.7 . . ?
C00R C00S C1 110.65(15) . . ?
C1 C00S H00S 124.7 . . ?
S0 C00T H00D 120.6 . . ?
C00Q C00T S0 118.74(12) . . ?
C00Q C00T H00T 127.0 . . ?
C00Q C00T H00D 120.6 . . ?
C00Q C00T C003 106.0(3) . . ?
C003 C00T H00T 127.0 . . ?
C00F C1 C00S 112.9(3) . . ?
C00F C1 H1 123.6 . . ?
C00S C1 H1 123.6 . . ?
C00F C1A C00R 110.1(10) . . ?
C00F C1A H1A 125.0 . . ?
C00R C1A H1A 125.0 . . ?
C00G C003 C00T 113.5(5) . . ?
C00G C003 H003 123.3 . . ?
C00T C003 H003 123.3 . . ?
N005 C009 N006 126.71(10) . . ?
N005 C009 C00F 116.61(10) . . ?
N006 C009 C00F 116.68(10) . . ?

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
S0AA C00F C1 C00S 0.2(5) . . . . ?
S0AA C00F C009 N005 3.36(14) . . . . ?
S0AA C00F C009 N006 -177.09(9) . . . . ?
S0AA C00R C00S C1 -0.1(3) . . . . ?
S0AB C00F C1A C00R 1.5(15) . . . . ?
S0AB C00F C009 N005 -177.7(3) . . . . ?
S0AB C00F C009 N006 1.9(3) . . . . ?
S002 C00G C003 C00T 0.3(7) . . . . ?
S002 C00Q C00T C003 3.0(4) . . . . ?
N004 C00B C00G S0 160.28(12) . . . . ?
N004 C00B C00G S002 -18.69(15) . . . . ?
N004 C00B C00G C0 -20.0(5) . . . . ?
N004 C00B C00G C003 161.2(5) . . . . ?
N006 C00B C00G S0 -20.21(16) . . . . ?
N006 C00B C00G S002 160.82(11) . . . . ?
N006 C00B C00G C0 159.6(5) . . . . ?
N006 C00B C00G C003 -19.2(5) . . . . ?
N008 C00C C00E C00I -173.53(10) . . . . ?
N008 C00C C00J C00P 173.96(10) . . . . ?
N008 C00D C00H C00M 176.22(10) . . . . ?
N008 C00D C00L C00N -176.87(11) . . . . ?
C0 C00Q C00T S0 1.0(4) . . . . ?
C00A N004 C00B N006 -0.33(16) . . . . ?
C00A N004 C00B C00G 179.13(9) . . . . ?
C00A N005 C009 N006 -0.59(16) . . . . ?
C00A N005 C009 C00F 178.91(9) . . . . ?
C00A N008 C00C C00E -67.73(14) . . . . ?
C00A N008 C00C C00J 117.11(12) . . . . ?
C00A N008 C00D C00H 127.96(11) . . . . ?
C00A N008 C00D C00L -55.66(15) . . . . ?
C00B N004 C00A N005 -4.73(16) . . . . ?
C00B N004 C00A N008 173.93(9) . . . . ?
C00B N006 C009 N005 -3.65(16) . . . . ?
C00B N006 C009 C00F 176.85(9) . . . . ?
C00B C00G C003 C00T -179.6(3) . . . . ?
C00C N008 C00A N004 175.72(10) . . . . ?
C00C N008 C00A N005 -5.52(15) . . . . ?
C00C N008 C00D C00H -55.42(13) . . . . ?
C00C N008 C00D C00L 120.96(12) . . . . ?
C00C C00E C00I C00K -0.16(18) . . . . ?
C00C C00J C00P C00K -0.49(18) . . . . ?
C00D N008 C00A N004 -7.88(15) . . . . ?
C00D N008 C00A N005 170.88(10) . . . . ?
C00D N008 C00C C00E 115.69(11) . . . . ?
C00D N008 C00C C00J -59.47(13) . . . . ?
C00D C00H C00M C00O 0.36(18) . . . . ?
C00D C00L C00N C00O 1.13(19) . . . . ?
C00E C00C C00J C00P -1.19(17) . . . . ?
C00E C00I C00K C00P -1.51(18) . . . . ?
C00F S0AA C00R C00S 0.18(12) . . . . ?
C00F S0AB C00S C00R 1.0(4) . . . . ?
C00G S0 C00T C00Q -0.72(17) . . . . ?
C00G S002 C00Q C00T -2.54(15) . . . . ?
C00G C0 C00Q C00T -0.9(7) . . . . ?
C00H C00D C00L C00N -0.57(17) . . . . ?
C00H C00M C00O C00N 0.19(18) . . . . ?
C00I C00K C00P C00J 1.83(18) . . . . ?
C00J C00C C00E C00I 1.51(17) . . . . ?
C00L C00D C00H C00M -0.17(17) . . . . ?
C00L C00N C00O C00M -0.94(19) . . . . ?
C00Q S002 C00G C00B -178.92(10) . . . . ?
C00Q S002 C00G C003 1.1(4) . . . . ?
C00Q C0 C00G S0 0.5(7) . . . . ?
C00Q C0 C00G C00B -179.3(3) . . . . ?
C00Q C00T C003 C00G -1.9(7) . . . . ?
C00R S0AA C00F C1 -0.2(3) . . . . ?
C00R S0AA C00F C009 179.49(10) . . . . ?
C00R C00S C1 C00F -0.1(5) . . . . ?
C00S S0AB C00F C1A -1.4(10) . . . . ?
C00S S0AB C00F C009 -179.84(16) . . . . ?
C00S C00R C1A C00F -0.7(13) . . . . ?
C00T S0 C00G C0 0.1(4) . . . . ?
C00T S0 C00G C00B 179.91(10) . . . . ?
C1 C00F C009 N005 -177.0(4) . . . . ?
C1 C00F C009 N006 2.6(4) . . . . ?
C1A C00F C009 N005 4.1(11) . . . . ?
C1A C00F C009 N006 -176.3(11) . . . . ?
C1A C00R C00S S0AB -0.3(8) . . . . ?
C009 N005 C00A N004 5.13(15) . . . . ?
C009 N005 C00A N008 -173.52(9) . . . . ?
C009 N006 C00B N004 4.15(16) . . . . ?
C009 N006 C00B C00G -175.31(9) . . . . ?
C009 C00F C1 C00S -179.5(2) . . . . ?
C009 C00F C1A C00R 179.8(5) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_z
_database_code_depnum_ccdc_archive 'CCDC 1435751'
_audit_update_record             
;
2015-11-07 deposited with the CCDC.
2016-08-08 downloaded from the CCDC.
;
_audit_creation_date             2015-11-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         '2(C12 H9 N3 O S2)'
_chemical_formula_sum            'C24 H18 N6 O2 S4'
_chemical_formula_weight         550.68
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
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                   30.6659(15)
_cell_length_b                   7.7991(4)
_cell_length_c                   21.6105(11)
_cell_angle_alpha                90
_cell_angle_beta                 97.152(2)
_cell_angle_gamma                90
_cell_volume                     5128.3(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9060
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      26.33
_cell_measurement_theta_min      2.70
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.405
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6915
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1201 before and 0.0589 after correction.
The Ratio of minimum to maximum transmission is 0.9277.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.426
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2272
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0466
_diffrn_reflns_av_unetI/netI     0.0200
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            71086
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.430
_diffrn_reflns_theta_min         2.696
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4115
_reflns_number_total             5237
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       0.0021(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     385
_refine_ls_number_reflns         5237
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0601
_refine_ls_R_factor_gt           0.0422
_refine_ls_restrained_S_all      1.077
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0495P)²+3.2453P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1024
_refine_ls_wR_factor_ref         0.1126
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(H00F)=Sof(H01A)=Sof(S0)=Sof(C0)=Sof(H0)=1-FVAR(1)
 Sof(S004)=Sof(C006)=Sof(H006)=Sof(H00Z)=Sof(H010)=FVAR(1)
 Sof(H00A)=Sof(H00B)=Sof(S0AB)=Sof(CA)=Sof(HA)=1-FVAR(2)
 Sof(S0AA)=Sof(C)=Sof(H)=Sof(H00Q)=Sof(H00U)=FVAR(2)
 Sof(H00G)=Sof(H00H)=Sof(SA)=Sof(C1)=Sof(H1)=1-FVAR(3)
 Sof(S)=Sof(C007)=Sof(H007)=Sof(H00S)=Sof(H00T)=FVAR(3)
3.a Aromatic/amide H refined with riding coordinates:
 C(H), C006(H006), C007(H007), C00O(H00O), C00Q(H00Q), C00Q(H00A), C00R(H00R),
 C00S(H00S), C00S(H00G), C00T(H00T), C00T(H00H), C00U(H00U), C00U(H00B),
 C00V(H00V), C00Z(H00Z), C00Z(H00F), C010(H010), C010(H01A), C0(H0), CA(HA),
 C1(H1)
3.b Idealised Me refined as rotating group:
 C00X(H00I,H00J,H00K), C00Y(H00C,H00D,H00E)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
S001 S 0.45633(2) 0.37703(7) 0.56436(3) 0.06111(18) Uani 1 1 d . . . . .
S S 0.27688(10) 0.7196(4) 0.75603(12) 0.0632(5) Uani 0.669(3) 1 d . . P A 1
S0AA S 0.63637(9) 0.3478(4) 0.58893(10) 0.0616(5) Uani 0.606(4) 1 d . . P B 1
S004 S 0.66081(12) -0.0681(6) 0.3235(2) 0.0666(8) Uani 0.461(3) 1 d . . P C 1
C C 0.6939(4) 0.1967(17) 0.5343(6) 0.075(4) Uani 0.606(4) 1 d . . P B 1
H H 0.7076 0.1366 0.5049 0.090 Uiso 0.606(4) 1 calc R . P B 1
C006 C 0.5785(5) -0.090(3) 0.2830(7) 0.072(4) Uani 0.461(3) 1 d . . P C 1
H006 H 0.5480 -0.0843 0.2805 0.087 Uiso 0.461(3) 1 calc R . P C 1
C007 C 0.3648(4) 0.7358(13) 0.8019(4) 0.0395(19) Uani 0.669(3) 1 d . . P A 1
H007 H 0.3952 0.7270 0.8073 0.047 Uiso 0.669(3) 1 calc R . P A 1
O008 O 0.29266(4) 0.4054(2) 0.55780(7) 0.0668(4) Uani 1 1 d . . . . .
O009 O 0.50207(5) 0.1648(2) 0.45491(8) 0.0728(4) Uani 1 1 d . . . . .
N00A N 0.38556(5) 0.57465(19) 0.68909(7) 0.0457(4) Uani 1 1 d . . . . .
N00B N 0.36582(5) 0.44127(19) 0.59039(7) 0.0471(4) Uani 1 1 d . . . . .
N00C N 0.31027(5) 0.5357(2) 0.64960(7) 0.0523(4) Uani 1 1 d . . . . .
N00D N 0.57280(5) 0.1939(2) 0.49071(8) 0.0557(4) Uani 1 1 d . . . . .
N00E N 0.62712(5) 0.0926(2) 0.43043(7) 0.0536(4) Uani 1 1 d . . . . .
N00F N 0.55150(6) 0.0665(2) 0.39173(8) 0.0575(4) Uani 1 1 d . . . . .
C00G C 0.39507(5) 0.4986(2) 0.63658(8) 0.0424(4) Uani 1 1 d . . . . .
C00H C 0.34244(6) 0.5898(2) 0.69227(8) 0.0457(4) Uani 1 1 d . . . . .
C00I C 0.44131(6) 0.4766(2) 0.62924(8) 0.0457(4) Uani 1 1 d . . . . .
C00J C 0.61425(6) 0.1673(2) 0.48095(8) 0.0489(4) Uani 1 1 d . . . . .
C00K C 0.32453(6) 0.4623(2) 0.60027(9) 0.0491(4) Uani 1 1 d . . . . .
C00L C 0.64861(7) 0.2241(2) 0.52902(8) 0.0512(5) Uani 1 1 d . . . . .
C00M C 0.54341(7) 0.1392(3) 0.44436(10) 0.0564(5) Uani 1 1 d . . . . .
C00N C 0.32988(6) 0.6737(2) 0.74803(9) 0.0500(5) Uani 1 1 d . . . . .
C00O C 0.47714(6) 0.5241(3) 0.67068(10) 0.0589(5) Uani 1 1 d . . . . .
H00O H 0.4756 0.5793 0.7085 0.071 Uiso 1 1 calc R . . . .
C00P C 0.59435(7) 0.0458(2) 0.38758(9) 0.0523(5) Uani 1 1 d . . . . .
C00Q C 0.68807(8) 0.3539(3) 0.61930(10) 0.0708(6) Uani 1 1 d . . . . .
H00Q H 0.6968 0.4132 0.6561 0.085 Uiso 0.606(4) 1 calc R . P B 1
H00A H 0.6936 0.4199 0.6552 0.085 Uiso 0.394(4) 1 calc R . P B 2
C00R C 0.51022(7) 0.3983(3) 0.59148(12) 0.0687(6) Uani 1 1 d . . . . .
H00R H 0.5329 0.3599 0.5702 0.082 Uiso 1 1 calc R . . . .
C00S C 0.28971(9) 0.8121(4) 0.82291(13) 0.0825(8) Uani 1 1 d . . . . .
H00S H 0.2685 0.8586 0.8453 0.099 Uiso 0.669(3) 1 calc R . P A 1
H00G H 0.2668 0.8590 0.8417 0.099 Uiso 0.331(3) 1 calc R . P A 2
C00T C 0.33244(9) 0.8176(3) 0.84394(11) 0.0737(6) Uani 1 1 d . . . . .
H00T H 0.3426 0.8681 0.8820 0.088 Uiso 0.669(3) 1 calc R . P A 1
H00H H 0.3436 0.8708 0.8811 0.088 Uiso 0.331(3) 1 calc R . P A 2
C00U C 0.71721(8) 0.2704(3) 0.58924(11) 0.0717(6) Uani 1 1 d . . . . .
H00U H 0.7472 0.2619 0.6019 0.086 Uiso 0.606(4) 1 calc R . P B 1
H00B H 0.7470 0.2731 0.6042 0.086 Uiso 0.394(4) 1 calc R . P B 2
C00V C 0.51663(7) 0.4767(3) 0.64730(12) 0.0722(6) Uani 1 1 d . . . . .
H00V H 0.5444 0.4979 0.6686 0.087 Uiso 1 1 calc R . . . .
C00W C 0.60607(8) -0.0349(2) 0.33102(10) 0.0585(5) Uani 1 1 d . . . . .
C00X C 0.30607(8) 0.3200(4) 0.50420(11) 0.0789(7) Uani 1 1 d . . . . .
H00I H 0.2807 0.2957 0.4748 0.118 Uiso 1 1 calc GR . . . .
H00J H 0.3207 0.2147 0.5170 0.118 Uiso 1 1 calc GR . . . .
H00K H 0.3258 0.3927 0.4850 0.118 Uiso 1 1 calc GR . . . .
C00Y C 0.46772(8) 0.1040(4) 0.40870(14) 0.0879(8) Uani 1 1 d . . . . .
H00C H 0.4721 0.1491 0.3686 0.132 Uiso 1 1 calc GR . . . .
H00D H 0.4398 0.1414 0.4193 0.132 Uiso 1 1 calc GR . . . .
H00E H 0.4684 -0.0190 0.4074 0.132 Uiso 1 1 calc GR . . . .
C00Z C 0.64581(11) -0.1560(3) 0.25495(12) 0.0846(8) Uani 1 1 d . . . . .
H00Z H 0.6671 -0.1991 0.2320 0.102 Uiso 0.461(3) 1 calc R . P C 1
H00F H 0.6702 -0.1909 0.2366 0.102 Uiso 0.539(3) 1 calc R . P C 2
C010 C 0.60376(12) -0.1660(3) 0.23202(13) 0.0909(8) Uani 1 1 d . . . . .
H010 H 0.5920 -0.2094 0.1934 0.109 Uiso 0.461(3) 1 calc R . P C 1
H01A H 0.5958 -0.2175 0.1935 0.109 Uiso 0.539(3) 1 calc R . P C 2
S0 S 0.56565(16) -0.0883(8) 0.2712(2) 0.0839(10) Uani 0.539(3) 1 d . . P C 2
C0 C 0.6447(3) -0.0768(19) 0.3161(7) 0.070(3) Uani 0.539(3) 1 d . . P C 2
H0 H 0.6703 -0.0570 0.3430 0.084 Uiso 0.539(3) 1 calc R . P C 2
S0AB S 0.69986(16) 0.1638(8) 0.5259(3) 0.0634(9) Uani 0.394(4) 1 d . . P B 2
CA C 0.6467(5) 0.319(2) 0.5839(7) 0.082(6) Uani 0.394(4) 1 d . . P B 2
HA H 0.6203 0.3561 0.5962 0.099 Uiso 0.394(4) 1 calc R . P B 2
SA S 0.3609(3) 0.7294(12) 0.8016(4) 0.086(3) Uani 0.331(3) 1 d . . P A 2
C1 C 0.2863(6) 0.717(3) 0.7639(10) 0.075(7) Uani 0.331(3) 1 d . . P A 2
H1 H 0.2600 0.6875 0.7399 0.091 Uiso 0.331(3) 1 calc R . 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
S001 C00I 1.7153(18) . ?
S001 C00R 1.691(2) . ?
S C00N 1.694(3) . ?
S C00S 1.619(4) . ?
S0AA C00L 1.694(3) . ?
S0AA C00Q 1.639(3) . ?
S004 C00W 1.726(4) . ?
S004 C00Z 1.646(5) . ?
C H 0.9300 . ?
C C00L 1.397(12) . ?
C C00U 1.428(12) . ?
C006 H006 0.9300 . ?
C006 C00W 1.327(14) . ?
C006 C010 1.543(17) . ?
C007 H007 0.9300 . ?
C007 C00N 1.557(10) . ?
C007 C00T 1.562(10) . ?
O008 C00K 1.331(2) . ?
O008 C00X 1.440(3) . ?
O009 C00M 1.331(2) . ?
O009 C00Y 1.439(3) . ?
N00A C00G 1.344(2) . ?
N00A C00H 1.338(2) . ?
N00B C00G 1.333(2) . ?
N00B C00K 1.320(2) . ?
N00C C00H 1.332(2) . ?
N00C C00K 1.331(2) . ?
N00D C00J 1.330(2) . ?
N00D C00M 1.332(3) . ?
N00E C00J 1.339(2) . ?
N00E C00P 1.330(2) . ?
N00F C00M 1.322(3) . ?
N00F C00P 1.338(3) . ?
C00G C00I 1.457(2) . ?
C00H C00N 1.465(3) . ?
C00I C00O 1.379(3) . ?
C00J C00L 1.454(3) . ?
C00L S0AB 1.650(5) . ?
C00L CA 1.404(14) . ?
C00N SA 1.470(9) . ?
C00N C1 1.459(19) . ?
C00O H00O 0.9300 . ?
C00O C00V 1.418(3) . ?
C00P C00W 1.459(3) . ?
C00Q H00Q 0.9300 . ?
C00Q H00A 0.9300 . ?
C00Q C00U 1.337(3) . ?
C00Q CA 1.424(16) . ?
C00R H00R 0.9300 . ?
C00R C00V 1.345(3) . ?
C00S H00S 0.9300 . ?
C00S H00G 0.9300 . ?
C00S C00T 1.333(4) . ?
C00S C1 1.47(2) . ?
C00T H00T 0.9300 . ?
C00T H00H 0.9300 . ?
C00T SA 1.507(9) . ?
C00U H00U 0.9300 . ?
C00U H00B 0.9300 . ?
C00U S0AB 1.632(6) . ?
C00V H00V 0.9300 . ?
C00W S0 1.727(4) . ?
C00W C0 1.307(12) . ?
C00X H00I 0.9600 . ?
C00X H00J 0.9600 . ?
C00X H00K 0.9600 . ?
C00Y H00C 0.9600 . ?
C00Y H00D 0.9600 . ?
C00Y H00E 0.9600 . ?
C00Z H00Z 0.9300 . ?
C00Z H00F 0.9300 . ?
C00Z C010 1.325(4) . ?
C00Z C0 1.462(14) . ?
C010 H010 0.9300 . ?
C010 H01A 0.9300 . ?
C010 S0 1.642(6) . ?
C0 H0 0.9300 . ?
CA HA 0.9300 . ?
C1 H1 0.9300 . ?

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
C00R S001 C00I 91.30(10) . . ?
C00S S C00N 93.20(19) . . ?
C00Q S0AA C00L 91.56(17) . . ?
C00Z S004 C00W 88.9(2) . . ?
C00L C H 123.4 . . ?
C00L C C00U 113.3(8) . . ?
C00U C H 123.4 . . ?
C00W C006 H006 124.6 . . ?
C00W C006 C010 110.7(11) . . ?
C010 C006 H006 124.6 . . ?
C00N C007 H007 131.1 . . ?
C00N C007 C00T 97.8(6) . . ?
C00T C007 H007 131.1 . . ?
C00K O008 C00X 116.77(16) . . ?
C00M O009 C00Y 117.55(19) . . ?
C00H N00A C00G 113.69(15) . . ?
C00K N00B C00G 114.00(16) . . ?
C00K N00C C00H 113.67(15) . . ?
C00J N00D C00M 113.66(17) . . ?
C00P N00E C00J 114.39(17) . . ?
C00M N00F C00P 113.62(17) . . ?
N00A C00G C00I 117.40(16) . . ?
N00B C00G N00A 125.70(15) . . ?
N00B C00G C00I 116.89(16) . . ?
N00A C00H C00N 116.40(16) . . ?
N00C C00H N00A 126.03(17) . . ?
N00C C00H C00N 117.57(15) . . ?
C00G C00I S001 120.43(14) . . ?
C00O C00I S001 112.29(13) . . ?
C00O C00I C00G 127.26(17) . . ?
N00D C00J N00E 125.56(18) . . ?
N00D C00J C00L 117.44(17) . . ?
N00E C00J C00L 117.00(17) . . ?
O008 C00K N00C 114.17(16) . . ?
N00B C00K O008 118.94(17) . . ?
N00B C00K N00C 126.89(17) . . ?
C C00L S0AA 109.7(5) . . ?
C C00L C00J 129.6(5) . . ?
C00J C00L S0AA 120.66(16) . . ?
C00J C00L S0AB 119.6(2) . . ?
CA C00L C00J 131.4(6) . . ?
CA C00L S0AB 108.9(6) . . ?
O009 C00M N00D 113.15(18) . . ?
N00F C00M O009 119.78(19) . . ?
N00F C00M N00D 127.07(19) . . ?
C007 C00N S 115.9(4) . . ?
C00H C00N S 122.18(17) . . ?
C00H C00N C007 121.9(4) . . ?
C00H C00N SA 124.7(4) . . ?
C1 C00N C00H 129.6(9) . . ?
C1 C00N SA 105.6(9) . . ?
C00I C00O H00O 124.9 . . ?
C00I C00O C00V 110.2(2) . . ?
C00V C00O H00O 124.9 . . ?
N00E C00P N00F 125.69(18) . . ?
N00E C00P C00W 117.27(19) . . ?
N00F C00P C00W 117.04(19) . . ?
S0AA C00Q H00Q 121.2 . . ?
C00U C00Q S0AA 117.6(2) . . ?
C00U C00Q H00Q 121.2 . . ?
C00U C00Q H00A 127.8 . . ?
C00U C00Q CA 104.5(5) . . ?
CA C00Q H00A 127.8 . . ?
S001 C00R H00R 123.8 . . ?
C00V C00R S001 112.49(16) . . ?
C00V C00R H00R 123.8 . . ?
S C00S H00S 122.0 . . ?
C00T C00S S 116.0(2) . . ?
C00T C00S H00S 122.0 . . ?
C00T C00S H00G 127.1 . . ?
C00T C00S C1 105.8(8) . . ?
C1 C00S H00G 127.1 . . ?
C007 C00T H00T 121.4 . . ?
C00S C00T C007 117.2(4) . . ?
C00S C00T H00T 121.4 . . ?
C00S C00T H00H 123.3 . . ?
C00S C00T SA 113.4(4) . . ?
SA C00T H00H 123.3 . . ?
C C00U H00U 126.1 . . ?
C00Q C00U C 107.8(5) . . ?
C00Q C00U H00U 126.1 . . ?
C00Q C00U H00B 120.4 . . ?
C00Q C00U S0AB 119.2(3) . . ?
S0AB C00U H00B 120.4 . . ?
C00O C00V H00V 123.1 . . ?
C00R C00V C00O 113.7(2) . . ?
C00R C00V H00V 123.1 . . ?
C006 C00W S004 114.3(8) . . ?
C006 C00W C00P 126.5(7) . . ?
C00P C00W S004 119.2(2) . . ?
C00P C00W S0 120.2(3) . . ?
C0 C00W C00P 129.8(6) . . ?
C0 C00W S0 110.0(6) . . ?
O008 C00X H00I 109.5 . . ?
O008 C00X H00J 109.5 . . ?
O008 C00X H00K 109.5 . . ?
H00I C00X H00J 109.5 . . ?
H00I C00X H00K 109.5 . . ?
H00J C00X H00K 109.5 . . ?
O009 C00Y H00C 109.5 . . ?
O009 C00Y H00D 109.5 . . ?
O009 C00Y H00E 109.5 . . ?
H00C C00Y H00D 109.5 . . ?
H00C C00Y H00E 109.5 . . ?
H00D C00Y H00E 109.5 . . ?
S004 C00Z H00Z 119.6 . . ?
C010 C00Z S004 120.8(3) . . ?
C010 C00Z H00Z 119.6 . . ?
C010 C00Z H00F 128.3 . . ?
C010 C00Z C0 103.4(4) . . ?
C0 C00Z H00F 128.3 . . ?
C006 C010 H010 127.4 . . ?
C00Z C010 C006 105.2(6) . . ?
C00Z C010 H010 127.4 . . ?
C00Z C010 H01A 119.8 . . ?
C00Z C010 S0 120.5(3) . . ?
S0 C010 H01A 119.8 . . ?
C010 S0 C00W 89.1(3) . . ?
C00W C0 C00Z 117.0(7) . . ?
C00W C0 H0 121.5 . . ?
C00Z C0 H0 121.5 . . ?
C00U S0AB C00L 91.9(3) . . ?
C00L CA C00Q 115.3(8) . . ?
C00L CA HA 122.4 . . ?
C00Q CA HA 122.4 . . ?
C00N SA C00T 104.2(5) . . ?
C00N C1 C00S 110.6(14) . . ?
C00N C1 H1 124.7 . . ?
C00S C1 H1 124.7 . . ?

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
S001 C00I C00O C00V 0.1(2) . . . . ?
S001 C00R C00V C00O -0.2(3) . . . . ?
S C00N SA C00T -2.7(7) . . . . ?
S C00N C1 C00S -159(8) . . . . ?
S C00S C00T C007 0.3(5) . . . . ?
S C00S C00T SA -2.1(5) . . . . ?
S C00S C1 C00N 164(6) . . . . ?
S0AA C00L S0AB C00U -1.8(4) . . . . ?
S0AA C00L CA C00Q -163(5) . . . . ?
S0AA C00Q C00U C 1.4(7) . . . . ?
S0AA C00Q C00U S0AB -1.7(4) . . . . ?
S0AA C00Q CA C00L 166(5) . . . . ?
S004 C00W S0 C010 3.6(4) . . . . ?
S004 C00W C0 C00Z -169(5) . . . . ?
S004 C00Z C010 C006 -2.3(9) . . . . ?
S004 C00Z C010 S0 0.9(5) . . . . ?
S004 C00Z C0 C00W 173(3) . . . . ?
C C00L S0AB C00U 15(4) . . . . ?
C C00L CA C00Q 2.3(14) . . . . ?
C C00U S0AB C00L -13(4) . . . . ?
C006 C00W S0 C010 -24(9) . . . . ?
C006 C00W C0 C00Z 3.1(15) . . . . ?
C006 C010 S0 C00W 9(4) . . . . ?
C007 C00N SA C00T 139(11) . . . . ?
C007 C00N C1 C00S 3.3(15) . . . . ?
C007 C00T SA C00N -148(10) . . . . ?
N00A C00G C00I S001 178.73(12) . . . . ?
N00A C00G C00I C00O 0.6(3) . . . . ?
N00A C00H C00N S 174.09(18) . . . . ?
N00A C00H C00N C007 -2.3(5) . . . . ?
N00A C00H C00N SA -4.8(5) . . . . ?
N00A C00H C00N C1 176.7(11) . . . . ?
N00B C00G C00I S001 -1.3(2) . . . . ?
N00B C00G C00I C00O -179.47(18) . . . . ?
N00C C00H C00N S -5.9(3) . . . . ?
N00C C00H C00N C007 177.8(5) . . . . ?
N00C C00H C00N SA 175.2(5) . . . . ?
N00C C00H C00N C1 -3.2(11) . . . . ?
N00D C00J C00L S0AA -9.8(3) . . . . ?
N00D C00J C00L C 172.4(8) . . . . ?
N00D C00J C00L S0AB 168.9(3) . . . . ?
N00D C00J C00L CA -6.5(10) . . . . ?
N00E C00J C00L S0AA 170.06(18) . . . . ?
N00E C00J C00L C -7.7(8) . . . . ?
N00E C00J C00L S0AB -11.3(3) . . . . ?
N00E C00J C00L CA 173.4(10) . . . . ?
N00E C00P C00W S004 1.1(3) . . . . ?
N00E C00P C00W C006 -179.9(12) . . . . ?
N00E C00P C00W S0 -176.3(3) . . . . ?
N00E C00P C00W C0 3.3(9) . . . . ?
N00F C00P C00W S004 -179.0(2) . . . . ?
N00F C00P C00W C006 0.0(12) . . . . ?
N00F C00P C00W S0 3.6(3) . . . . ?
N00F C00P C00W C0 -176.8(8) . . . . ?
C00G N00A C00H N00C 0.8(3) . . . . ?
C00G N00A C00H C00N -179.22(15) . . . . ?
C00G N00B C00K O008 -178.24(16) . . . . ?
C00G N00B C00K N00C 1.5(3) . . . . ?
C00G C00I C00O C00V 178.44(18) . . . . ?
C00H N00A C00G N00B 0.1(2) . . . . ?
C00H N00A C00G C00I -179.91(15) . . . . ?
C00H N00C C00K O008 178.99(16) . . . . ?
C00H N00C C00K N00B -0.7(3) . . . . ?
C00H C00N SA C00T 176.3(3) . . . . ?
C00H C00N C1 C00S -175.8(5) . . . . ?
C00I S001 C00R C00V 0.20(19) . . . . ?
C00I C00O C00V C00R 0.0(3) . . . . ?
C00J N00D C00M O009 179.29(16) . . . . ?
C00J N00D C00M N00F -1.0(3) . . . . ?
C00J N00E C00P N00F -0.5(3) . . . . ?
C00J N00E C00P C00W 179.45(15) . . . . ?
C00J C00L S0AB C00U 179.49(19) . . . . ?
C00J C00L CA C00Q -178.6(5) . . . . ?
C00K N00B C00G N00A -1.1(2) . . . . ?
C00K N00B C00G C00I 178.91(15) . . . . ?
C00K N00C C00H N00A -0.5(3) . . . . ?
C00K N00C C00H C00N 179.48(16) . . . . ?
C00L S0AA C00Q C00U 0.3(3) . . . . ?
C00L S0AA C00Q CA -11(3) . . . . ?
C00L C C00U C00Q -2.9(11) . . . . ?
C00L C C00U S0AB 164(5) . . . . ?
C00M N00D C00J N00E -0.3(3) . . . . ?
C00M N00D C00J C00L 179.60(16) . . . . ?
C00M N00F C00P N00E -0.6(3) . . . . ?
C00M N00F C00P C00W 179.51(16) . . . . ?
C00N S C00S C00T 0.4(3) . . . . ?
C00N S C00S C1 -13(5) . . . . ?
C00N C007 C00T C00S -0.8(7) . . . . ?
C00N C007 C00T SA 30(9) . . . . ?
C00P N00E C00J N00D 0.9(3) . . . . ?
C00P N00E C00J C00L -178.95(16) . . . . ?
C00P N00F C00M O009 -178.93(17) . . . . ?
C00P N00F C00M N00D 1.4(3) . . . . ?
C00P C00W S0 C010 -179.1(2) . . . . ?
C00P C00W C0 C00Z -179.6(5) . . . . ?
C00Q S0AA C00L C -2.0(7) . . . . ?
C00Q S0AA C00L C00J 179.79(17) . . . . ?
C00Q S0AA C00L S0AB 1.1(3) . . . . ?
C00Q S0AA C00L CA 13(4) . . . . ?
C00Q C00U S0AB C00L 2.0(4) . . . . ?
C00R S001 C00I C00G -178.63(15) . . . . ?
C00R S001 C00I C00O -0.20(16) . . . . ?
C00S S C00N C007 -0.9(5) . . . . ?
C00S S C00N C00H -177.47(18) . . . . ?
C00S S C00N SA 1.5(5) . . . . ?
C00S S C00N C1 18(7) . . . . ?
C00S C00T SA C00N 2.9(7) . . . . ?
C00T C007 C00N S 1.1(7) . . . . ?
C00T C007 C00N C00H 177.6(3) . . . . ?
C00T C007 C00N SA -38(11) . . . . ?
C00T C007 C00N C1 -1.6(11) . . . . ?
C00T C00S C1 C00N -3.7(14) . . . . ?
C00U C C00L S0AA 3.2(12) . . . . ?
C00U C C00L C00J -178.8(5) . . . . ?
C00U C C00L S0AB -161(6) . . . . ?
C00U C C00L CA 0.3(13) . . . . ?
C00U C00Q CA C00L -4.2(14) . . . . ?
C00W S004 C00Z C010 1.3(3) . . . . ?
C00W S004 C00Z C0 -5(2) . . . . ?
C00W C006 C010 C00Z 2.4(16) . . . . ?
C00W C006 C010 S0 -167(5) . . . . ?
C00X O008 C00K N00B 1.5(3) . . . . ?
C00X O008 C00K N00C -178.20(19) . . . . ?
C00Y O009 C00M N00D -177.60(18) . . . . ?
C00Y O009 C00M N00F 2.7(3) . . . . ?
C00Z S004 C00W C006 0.3(11) . . . . ?
C00Z S004 C00W C00P 179.45(18) . . . . ?
C00Z S004 C00W S0 -3.2(4) . . . . ?
C00Z S004 C00W C0 8(4) . . . . ?
C00Z C010 S0 C00W -2.5(4) . . . . ?
C010 C006 C00W S004 -1.6(17) . . . . ?
C010 C006 C00W C00P 179.4(6) . . . . ?
C010 C006 C00W S0 153(10) . . . . ?
C010 C006 C00W C0 -3.2(16) . . . . ?
C010 C00Z C0 C00W -1.6(12) . . . . ?
S0 C00W C0 C00Z 0.0(12) . . . . ?
C0 C00W S0 C010 1.3(8) . . . . ?
C0 C00Z C010 C006 -0.5(11) . . . . ?
C0 C00Z C010 S0 2.8(7) . . . . ?
S0AB C00L CA C00Q 5.7(14) . . . . ?
CA C00L S0AB C00U -4.2(8) . . . . ?
CA C00Q C00U C 4.0(10) . . . . ?
CA C00Q C00U S0AB 0.8(8) . . . . ?
SA C00N C1 C00S 5.5(15) . . . . ?
C1 C00N SA C00T -4.9(10) . . . . ?
C1 C00S C00T C007 2.8(10) . . . . ?
C1 C00S C00T SA 0.4(10) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
