# 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_av56mf
_database_code_depnum_ccdc_archive 'CCDC 1038010'
_audit_update_record             
;
2014-12-08 deposited with the CCDC.
2016-07-06 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT601_av56mf              
;
PROBLEM:
PLAT601_ALERT_2_A Structure Contains Solvent Accessible 
VOIDS of .        459 A**3
RESPONSE: The highly disordered tolune solvent  
was removed using the SQUEEZE module in PLATON. An electron 
count of 110 was suggested per unit cell which relates 
two molecules of tolune. The files (.hkl and .ins) 
generated by PLATON after the SQUEEZE treatmet were 
used in the final refinement of the structure.  
;
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
4-(3,6-di-tert-butylcarbazol-9-yl)-N,N-bis(4-{[1,2,5]thiadiazolo[3,4-b]pyridin-6-yl}phenyl)aniline
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C48 H40 N8 S2'
_chemical_formula_sum            'C48 H40 N8 S2'
_chemical_formula_weight         793.00

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P-1   '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   12.4586(9)
_cell_length_b                   14.8169(10)
_cell_length_c                   15.6249(11)
_cell_angle_alpha                110.3700(10)
_cell_angle_beta                 99.7720(10)
_cell_angle_gamma                112.0440(10)
_cell_volume                     2351.8(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6154
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      23.79

_exptl_crystal_description       plate
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.120
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             832
_exptl_absorpt_coefficient_mu    0.153
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9372
_exptl_absorpt_correction_T_max  0.9819
_exptl_absorpt_process_details   'Bruker AXS SADABS program'

_exptl_special_details           
; 
Sheldrick,G.M.,(2003),University of gottingen,Germany 
;

_diffrn_ambient_temperature      293(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            8274
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0299
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.48
_diffrn_reflns_theta_max         25.00
_reflns_number_total             8274
_reflns_number_gt                6084
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.1179P)²+0.8339P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         8274
_refine_ls_number_parameters     529
_refine_ls_number_restraints     15
_refine_ls_R_factor_all          0.0913
_refine_ls_R_factor_gt           0.0712
_refine_ls_wR_factor_ref         0.2064
_refine_ls_wR_factor_gt          0.1928
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S2 S 0.20348(11) 1.14493(9) 0.20181(7) 0.0888(3) Uani 1 1 d . . .
S1 S -0.10770(11) 1.52500(9) 1.35594(10) 0.1079(4) Uani 1 1 d . . .
N8 N 0.3262(2) 0.84406(18) 0.95600(16) 0.0545(6) Uani 1 1 d . . .
C29 C 0.3636(2) 0.7695(2) 0.90778(19) 0.0499(6) Uani 1 1 d . . .
C34 C 0.3834(2) 0.7176(2) 0.96447(18) 0.0481(6) Uani 1 1 d . . .
N6 N 0.1792(3) 1.1148(2) 0.84642(18) 0.0660(7) Uani 1 1 d . . .
C39 C 0.3195(3) 0.8387(2) 1.04268(19) 0.0520(6) Uani 1 1 d . . .
C44 C 0.3544(2) 0.7614(2) 1.05024(19) 0.0487(6) Uani 1 1 d . . .
C41 C 0.2772(3) 0.8669(2) 1.1890(2) 0.0605(7) Uani 1 1 d . . .
H41 H 0.2507 0.9024 1.2358 0.073 Uiso 1 1 calc R . .
C15 C 0.1591(3) 1.1521(2) 0.4939(2) 0.0562(7) Uani 1 1 d . . .
C25 C 0.2173(3) 0.8737(2) 0.8309(2) 0.0543(7) Uani 1 1 d . . .
H25 H 0.1894 0.8021 0.7856 0.065 Uiso 1 1 calc R . .
C31 C 0.4263(3) 0.6698(2) 0.7915(2) 0.0599(7) Uani 1 1 d . . .
H31 H 0.4422 0.6542 0.7335 0.072 Uiso 1 1 calc R . .
C33 C 0.4228(3) 0.6395(2) 0.93086(19) 0.0516(6) Uani 1 1 d . . .
H33 H 0.4342 0.6040 0.9676 0.062 Uiso 1 1 calc R . .
C40 C 0.2800(3) 0.8913(2) 1.1120(2) 0.0610(7) Uani 1 1 d . . .
H40 H 0.2559 0.9420 1.1067 0.073 Uiso 1 1 calc R . .
C42 C 0.3122(3) 0.7910(2) 1.2003(2) 0.0550(7) Uani 1 1 d . . .
C8 C 0.0763(3) 1.1357(2) 0.9664(2) 0.0580(7) Uani 1 1 d . . .
H8 H 0.0642 1.0683 0.9625 0.070 Uiso 1 1 calc R . .
C26 C 0.2954(3) 0.9134(2) 0.92461(19) 0.0501(6) Uani 1 1 d . . .
C32 C 0.4450(3) 0.6139(2) 0.84405(19) 0.0527(6) Uani 1 1 d . . .
C23 C 0.2224(3) 1.0478(2) 0.8711(2) 0.0555(7) Uani 1 1 d . . .
C13 C 0.1482(3) 1.2010(3) 0.3405(2) 0.0641(8) Uani 1 1 d . . .
C27 C 0.3410(3) 1.0219(2) 0.9894(2) 0.0554(7) Uani 1 1 d . . .
H27 H 0.3967 1.0501 1.0514 0.066 Uiso 1 1 calc R . .
C17 C 0.1602(3) 1.1354(2) 0.5819(2) 0.0567(7) Uani 1 1 d . . .
C20 C 0.1709(3) 1.1168(2) 0.7559(2) 0.0588(7) Uani 1 1 d . . .
C43 C 0.3507(3) 0.7390(2) 1.12976(19) 0.0518(6) Uani 1 1 d . . .
H43 H 0.3745 0.6882 1.1352 0.062 Uiso 1 1 calc R . .
C24 C 0.1810(3) 0.9406(2) 0.8050(2) 0.0566(7) Uani 1 1 d . . .
H24 H 0.1278 0.9133 0.7423 0.068 Uiso 1 1 calc R . .
N5 N 0.1481(3) 1.2165(3) 0.2604(2) 0.0857(9) Uani 1 1 d . . .
C9 C 0.1377(3) 1.1759(2) 0.9112(2) 0.0578(7) Uani 1 1 d . . .
C4 C 0.0023(3) 1.3589(2) 1.0984(2) 0.0575(7) Uani 1 1 d . . .
C45 C 0.3079(3) 0.7714(3) 1.2899(2) 0.0697(7) Uani 1 1 d U . .
C35 C 0.4887(3) 0.5289(2) 0.8043(2) 0.0583(7) Uani 1 1 d . . .
C28 C 0.3049(3) 1.0881(2) 0.9632(2) 0.0560(7) Uani 1 1 d . . .
H28 H 0.3361 1.1607 1.0076 0.067 Uiso 1 1 calc R . .
C6 C 0.0496(3) 1.2956(2) 1.0340(2) 0.0548(7) Uani 1 1 d . . .
C5 C 0.0051(3) 1.3639(2) 1.1872(2) 0.0608(7) Uani 1 1 d . . .
H5 H 0.0369 1.3265 1.2112 0.073 Uiso 1 1 calc R . .
C7 C 0.0333(3) 1.1946(2) 1.0269(2) 0.0561(7) Uani 1 1 d . . .
H7 H -0.0074 1.1665 1.0636 0.067 Uiso 1 1 calc R . .
C1 C -0.0419(3) 1.4279(2) 1.2418(3) 0.0665(8) Uani 1 1 d . . .
C22 C 0.0696(3) 1.1360(3) 0.6233(2) 0.0619(7) Uani 1 1 d . . .
H22 H 0.0045 1.1434 0.5931 0.074 Uiso 1 1 calc R . .
C10 C 0.1560(3) 1.2777(2) 0.9195(2) 0.0633(8) Uani 1 1 d . . .
H10 H 0.1987 1.3068 0.8843 0.076 Uiso 1 1 calc R . .
C18 C 0.2535(3) 1.1211(3) 0.6283(2) 0.0666(8) Uani 1 1 d . . .
H18 H 0.3133 1.1170 0.6010 0.080 Uiso 1 1 calc R . .
C14 C 0.1124(3) 1.2226(3) 0.4798(2) 0.0724(9) Uani 1 1 d . . .
H14 H 0.0834 1.2534 0.5271 0.087 Uiso 1 1 calc R . .
C11 C 0.1117(3) 1.3352(2) 0.9791(2) 0.0622(8) Uani 1 1 d . . .
H11 H 0.1237 1.4025 0.9828 0.075 Uiso 1 1 calc R . .
N7 N 0.1060(3) 1.2484(3) 0.4078(2) 0.0840(9) Uani 1 1 d . . .
C16 C 0.2005(3) 1.1057(2) 0.4257(2) 0.0655(8) Uani 1 1 d . . .
H16 H 0.2313 1.0590 0.4315 0.079 Uiso 1 1 calc R . .
C19 C 0.2596(3) 1.1127(3) 0.7144(2) 0.0691(8) Uani 1 1 d . . .
H19 H 0.3238 1.1044 0.7445 0.083 Uiso 1 1 calc R . .
N3 N -0.0902(3) 1.4805(2) 1.1130(3) 0.0821(9) Uani 1 1 d . . .
C30 C 0.3861(3) 0.7460(2) 0.8207(2) 0.0563(7) Uani 1 1 d . . .
H30 H 0.3742 0.7808 0.7833 0.068 Uiso 1 1 calc R . .
C12 C 0.1962(3) 1.1293(2) 0.3458(2) 0.0607(7) Uani 1 1 d . . .
N4 N 0.2302(3) 1.0912(3) 0.2698(2) 0.0857(9) Uani 1 1 d . . .
C21 C 0.0745(3) 1.1259(2) 0.7076(2) 0.0623(7) Uani 1 1 d . . .
H21 H 0.0119 1.1251 0.7329 0.075 Uiso 1 1 calc R . .
C2 C -0.0863(3) 1.4859(3) 1.2018(3) 0.0745(9) Uani 1 1 d . . .
C3 C -0.0491(3) 1.4181(3) 1.0649(3) 0.0717(9) Uani 1 1 d . . .
H3 H -0.0531 1.4108 1.0027 0.086 Uiso 1 1 calc R . .
N1 N -0.0496(3) 1.4428(3) 1.3292(2) 0.0882(9) Uani 1 1 d . . .
N2 N -0.1247(3) 1.5469(2) 1.2621(3) 0.0956(10) Uani 1 1 d . . .
C38 C 0.5020(5) 0.4760(4) 0.8707(3) 0.1145(17) Uani 1 1 d . . .
H38A H 0.5604 0.5311 0.9340 0.172 Uiso 1 1 calc R . .
H38B H 0.5304 0.4242 0.8438 0.172 Uiso 1 1 calc R . .
H38C H 0.4234 0.4393 0.8762 0.172 Uiso 1 1 calc R . .
C37 C 0.3993(4) 0.4409(3) 0.7040(3) 0.1023(14) Uani 1 1 d . . .
H37A H 0.3193 0.4051 0.7076 0.153 Uiso 1 1 calc R . .
H37B H 0.4281 0.3886 0.6798 0.153 Uiso 1 1 calc R . .
H37C H 0.3940 0.4732 0.6608 0.153 Uiso 1 1 calc R . .
C36 C 0.6150(4) 0.5842(3) 0.7955(3) 0.0949(12) Uani 1 1 d . . .
H36A H 0.6082 0.6160 0.7520 0.142 Uiso 1 1 calc R . .
H36B H 0.6423 0.5311 0.7705 0.142 Uiso 1 1 calc R . .
H36C H 0.6734 0.6403 0.8584 0.142 Uiso 1 1 calc R . .
C47 C 0.4070(4) 0.8702(4) 1.3796(3) 0.1168(14) Uani 1 1 d U . .
H47A H 0.4865 0.8796 1.3764 0.175 Uiso 1 1 calc R . .
H47B H 0.3982 0.8606 1.4361 0.175 Uiso 1 1 calc R . .
H47C H 0.3994 0.9335 1.3834 0.175 Uiso 1 1 calc R . .
C48 C 0.3191(8) 0.6709(5) 1.2796(4) 0.186(4) Uani 1 1 d . . .
H48A H 0.4006 0.6827 1.2804 0.280 Uiso 1 1 calc R . .
H48B H 0.2594 0.6102 1.2192 0.280 Uiso 1 1 calc R . .
H48C H 0.3045 0.6556 1.3326 0.280 Uiso 1 1 calc R . .
C46 C 0.1857(4) 0.7529(4) 1.3039(3) 0.1119(12) Uani 1 1 d U . .
H46A H 0.1846 0.7406 1.3602 0.168 Uiso 1 1 calc R . .
H46B H 0.1200 0.6904 1.2476 0.168 Uiso 1 1 calc R . .
H46C H 0.1749 0.8160 1.3128 0.168 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
S2 N5 1.590(3) . ?
S2 N4 1.594(3) . ?
S1 N2 1.604(4) . ?
S1 N1 1.610(3) . ?
N8 C29 1.390(3) . ?
N8 C39 1.399(3) . ?
N8 C26 1.424(3) . ?
C29 C30 1.387(4) . ?
C29 C34 1.406(3) . ?
C34 C33 1.395(4) . ?
C34 C44 1.443(4) . ?
N6 C20 1.413(4) . ?
N6 C9 1.415(4) . ?
N6 C23 1.421(3) . ?
C39 C40 1.379(4) . ?
C39 C44 1.401(4) . ?
C44 C43 1.397(4) . ?
C41 C40 1.374(4) . ?
C41 C42 1.403(4) . ?
C41 H41 0.9300 . ?
C15 C16 1.347(4) . ?
C15 C14 1.431(4) . ?
C15 C17 1.479(4) . ?
C25 C24 1.380(4) . ?
C25 C26 1.387(4) . ?
C25 H25 0.9300 . ?
C31 C30 1.370(4) . ?
C31 C32 1.402(4) . ?
C31 H31 0.9300 . ?
C33 C32 1.382(4) . ?
C33 H33 0.9300 . ?
C40 H40 0.9300 . ?
C42 C43 1.380(4) . ?
C42 C45 1.531(4) . ?
C8 C7 1.375(4) . ?
C8 C9 1.387(4) . ?
C8 H8 0.9300 . ?
C26 C27 1.385(4) . ?
C32 C35 1.534(4) . ?
C23 C24 1.384(4) . ?
C23 C28 1.387(4) . ?
C13 N5 1.348(4) . ?
C13 N7 1.351(4) . ?
C13 C12 1.420(4) . ?
C27 C28 1.372(4) . ?
C27 H27 0.9300 . ?
C17 C18 1.389(4) . ?
C17 C22 1.395(4) . ?
C20 C19 1.382(4) . ?
C20 C21 1.382(4) . ?
C43 H43 0.9300 . ?
C24 H24 0.9300 . ?
C9 C10 1.392(4) . ?
C4 C5 1.357(4) . ?
C4 C3 1.441(4) . ?
C4 C6 1.483(4) . ?
C45 C48 1.503(5) . ?
C45 C47 1.503(5) . ?
C45 C46 1.511(5) . ?
C35 C37 1.514(5) . ?
C35 C38 1.525(5) . ?
C35 C36 1.533(5) . ?
C28 H28 0.9300 . ?
C6 C11 1.385(4) . ?
C6 C7 1.393(4) . ?
C5 C1 1.411(4) . ?
C5 H5 0.9300 . ?
C7 H7 0.9300 . ?
C1 N1 1.332(4) . ?
C1 C2 1.432(5) . ?
C22 C21 1.371(4) . ?
C22 H22 0.9300 . ?
C10 C11 1.368(4) . ?
C10 H10 0.9300 . ?
C18 C19 1.384(4) . ?
C18 H18 0.9300 . ?
C14 N7 1.308(4) . ?
C14 H14 0.9300 . ?
C11 H11 0.9300 . ?
C16 C12 1.407(4) . ?
C16 H16 0.9300 . ?
C19 H19 0.9300 . ?
N3 C3 1.298(4) . ?
N3 C2 1.354(5) . ?
C30 H30 0.9300 . ?
C12 N4 1.338(4) . ?
C21 H21 0.9300 . ?
C2 N2 1.348(4) . ?
C3 H3 0.9300 . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 0.9600 . ?
C37 H37A 0.9600 . ?
C37 H37B 0.9600 . ?
C37 H37C 0.9600 . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
C47 H47A 0.9600 . ?
C47 H47B 0.9600 . ?
C47 H47C 0.9600 . ?
C48 H48A 0.9600 . ?
C48 H48B 0.9600 . ?
C48 H48C 0.9600 . ?
C46 H46A 0.9600 . ?
C46 H46B 0.9600 . ?
C46 H46C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N5 S2 N4 101.51(14) . . ?
N2 S1 N1 101.83(17) . . ?
C29 N8 C39 108.3(2) . . ?
C29 N8 C26 127.8(2) . . ?
C39 N8 C26 123.9(2) . . ?
C30 C29 N8 130.2(2) . . ?
C30 C29 C34 120.8(2) . . ?
N8 C29 C34 108.9(2) . . ?
C33 C34 C29 119.2(2) . . ?
C33 C34 C44 133.8(2) . . ?
C29 C34 C44 106.9(2) . . ?
C20 N6 C9 119.3(2) . . ?
C20 N6 C23 120.9(2) . . ?
C9 N6 C23 119.6(2) . . ?
C40 C39 N8 130.3(2) . . ?
C40 C39 C44 120.7(2) . . ?
N8 C39 C44 108.9(2) . . ?
C43 C44 C39 119.4(2) . . ?
C43 C44 C34 133.7(2) . . ?
C39 C44 C34 106.9(2) . . ?
C40 C41 C42 123.1(3) . . ?
C40 C41 H41 118.4 . . ?
C42 C41 H41 118.4 . . ?
C16 C15 C14 117.4(3) . . ?
C16 C15 C17 124.1(3) . . ?
C14 C15 C17 118.5(3) . . ?
C24 C25 C26 119.9(3) . . ?
C24 C25 H25 120.0 . . ?
C26 C25 H25 120.0 . . ?
C30 C31 C32 123.9(3) . . ?
C30 C31 H31 118.0 . . ?
C32 C31 H31 118.0 . . ?
C32 C33 C34 121.2(2) . . ?
C32 C33 H33 119.4 . . ?
C34 C33 H33 119.4 . . ?
C41 C40 C39 118.3(3) . . ?
C41 C40 H40 120.8 . . ?
C39 C40 H40 120.8 . . ?
C43 C42 C41 117.5(2) . . ?
C43 C42 C45 123.5(2) . . ?
C41 C42 C45 119.0(3) . . ?
C7 C8 C9 120.6(3) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 H8 119.7 . . ?
C27 C26 C25 119.1(2) . . ?
C27 C26 N8 119.6(2) . . ?
C25 C26 N8 121.3(2) . . ?
C33 C32 C31 117.1(2) . . ?
C33 C32 C35 123.1(2) . . ?
C31 C32 C35 119.8(2) . . ?
C24 C23 C28 118.7(2) . . ?
C24 C23 N6 121.0(3) . . ?
C28 C23 N6 120.3(3) . . ?
N5 C13 N7 123.2(3) . . ?
N5 C13 C12 112.8(3) . . ?
N7 C13 C12 124.0(3) . . ?
C28 C27 C26 120.7(3) . . ?
C28 C27 H27 119.7 . . ?
C26 C27 H27 119.7 . . ?
C18 C17 C22 117.0(3) . . ?
C18 C17 C15 121.3(3) . . ?
C22 C17 C15 121.6(3) . . ?
C19 C20 C21 118.2(3) . . ?
C19 C20 N6 121.4(3) . . ?
C21 C20 N6 120.4(3) . . ?
C42 C43 C44 121.0(2) . . ?
C42 C43 H43 119.5 . . ?
C44 C43 H43 119.5 . . ?
C25 C24 C23 121.0(3) . . ?
C25 C24 H24 119.5 . . ?
C23 C24 H24 119.5 . . ?
C13 N5 S2 106.2(2) . . ?
C8 C9 C10 118.4(3) . . ?
C8 C9 N6 121.3(2) . . ?
C10 C9 N6 120.4(3) . . ?
C5 C4 C3 118.5(3) . . ?
C5 C4 C6 123.2(2) . . ?
C3 C4 C6 118.3(3) . . ?
C48 C45 C47 111.1(4) . . ?
C48 C45 C46 106.0(4) . . ?
C47 C45 C46 107.2(3) . . ?
C48 C45 C42 111.9(3) . . ?
C47 C45 C42 109.8(3) . . ?
C46 C45 C42 110.6(3) . . ?
C37 C35 C38 109.0(3) . . ?
C37 C35 C32 110.4(3) . . ?
C38 C35 C32 112.0(2) . . ?
C37 C35 C36 107.9(3) . . ?
C38 C35 C36 107.9(3) . . ?
C32 C35 C36 109.4(3) . . ?
C27 C28 C23 120.6(3) . . ?
C27 C28 H28 119.7 . . ?
C23 C28 H28 119.7 . . ?
C11 C6 C7 117.8(3) . . ?
C11 C6 C4 120.9(2) . . ?
C7 C6 C4 121.3(3) . . ?
C4 C5 C1 117.7(3) . . ?
C4 C5 H5 121.2 . . ?
C1 C5 H5 121.2 . . ?
C8 C7 C6 121.1(3) . . ?
C8 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
N1 C1 C5 127.6(3) . . ?
N1 C1 C2 114.0(3) . . ?
C5 C1 C2 118.4(3) . . ?
C21 C22 C17 121.3(3) . . ?
C21 C22 H22 119.3 . . ?
C17 C22 H22 119.3 . . ?
C11 C10 C9 120.6(3) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C19 C18 C17 121.5(3) . . ?
C19 C18 H18 119.2 . . ?
C17 C18 H18 119.2 . . ?
N7 C14 C15 127.2(3) . . ?
N7 C14 H14 116.4 . . ?
C15 C14 H14 116.4 . . ?
C10 C11 C6 121.5(3) . . ?
C10 C11 H11 119.3 . . ?
C6 C11 H11 119.3 . . ?
C14 N7 C13 114.3(3) . . ?
C15 C16 C12 118.8(3) . . ?
C15 C16 H16 120.6 . . ?
C12 C16 H16 120.6 . . ?
C20 C19 C18 120.5(3) . . ?
C20 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
C3 N3 C2 114.8(3) . . ?
C31 C30 C29 117.7(3) . . ?
C31 C30 H30 121.1 . . ?
C29 C30 H30 121.1 . . ?
N4 C12 C16 128.6(3) . . ?
N4 C12 C13 113.0(3) . . ?
C16 C12 C13 118.4(3) . . ?
C12 N4 S2 106.4(2) . . ?
C22 C21 C20 121.3(3) . . ?
C22 C21 H21 119.4 . . ?
C20 C21 H21 119.4 . . ?
N2 C2 N3 123.2(3) . . ?
N2 C2 C1 112.8(4) . . ?
N3 C2 C1 124.1(3) . . ?
N3 C3 C4 126.5(3) . . ?
N3 C3 H3 116.8 . . ?
C4 C3 H3 116.8 . . ?
C1 N1 S1 105.6(3) . . ?
C2 N2 S1 105.8(3) . . ?
C35 C38 H38A 109.5 . . ?
C35 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C35 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C35 C37 H37A 109.5 . . ?
C35 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
C35 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C35 C36 H36A 109.5 . . ?
C35 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C35 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C45 C47 H47A 109.5 . . ?
C45 C47 H47B 109.5 . . ?
H47A C47 H47B 109.5 . . ?
C45 C47 H47C 109.5 . . ?
H47A C47 H47C 109.5 . . ?
H47B C47 H47C 109.5 . . ?
C45 C48 H48A 109.5 . . ?
C45 C48 H48B 109.5 . . ?
H48A C48 H48B 109.5 . . ?
C45 C48 H48C 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 109.5 . . ?
C45 C46 H46A 109.5 . . ?
C45 C46 H46B 109.5 . . ?
H46A C46 H46B 109.5 . . ?
C45 C46 H46C 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 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
C39 N8 C29 C30 -178.5(3) . . . . ?
C26 N8 C29 C30 3.2(5) . . . . ?
C39 N8 C29 C34 -1.2(3) . . . . ?
C26 N8 C29 C34 -179.4(2) . . . . ?
C30 C29 C34 C33 -1.8(4) . . . . ?
N8 C29 C34 C33 -179.4(2) . . . . ?
C30 C29 C34 C44 178.7(3) . . . . ?
N8 C29 C34 C44 1.1(3) . . . . ?
C29 N8 C39 C40 -175.6(3) . . . . ?
C26 N8 C39 C40 2.7(5) . . . . ?
C29 N8 C39 C44 0.8(3) . . . . ?
C26 N8 C39 C44 179.2(2) . . . . ?
C40 C39 C44 C43 -0.9(4) . . . . ?
N8 C39 C44 C43 -177.8(2) . . . . ?
C40 C39 C44 C34 176.7(3) . . . . ?
N8 C39 C44 C34 -0.2(3) . . . . ?
C33 C34 C44 C43 -2.8(5) . . . . ?
C29 C34 C44 C43 176.5(3) . . . . ?
C33 C34 C44 C39 -179.9(3) . . . . ?
C29 C34 C44 C39 -0.6(3) . . . . ?
C29 C34 C33 C32 1.4(4) . . . . ?
C44 C34 C33 C32 -179.3(3) . . . . ?
C42 C41 C40 C39 -0.1(5) . . . . ?
N8 C39 C40 C41 176.8(3) . . . . ?
C44 C39 C40 C41 0.7(4) . . . . ?
C40 C41 C42 C43 -0.3(5) . . . . ?
C40 C41 C42 C45 178.9(3) . . . . ?
C24 C25 C26 C27 -3.4(4) . . . . ?
C24 C25 C26 N8 174.6(3) . . . . ?
C29 N8 C26 C27 -134.9(3) . . . . ?
C39 N8 C26 C27 47.1(4) . . . . ?
C29 N8 C26 C25 47.1(4) . . . . ?
C39 N8 C26 C25 -130.9(3) . . . . ?
C34 C33 C32 C31 0.0(4) . . . . ?
C34 C33 C32 C35 179.9(3) . . . . ?
C30 C31 C32 C33 -0.9(5) . . . . ?
C30 C31 C32 C35 179.2(3) . . . . ?
C20 N6 C23 C24 -45.1(4) . . . . ?
C9 N6 C23 C24 131.4(3) . . . . ?
C20 N6 C23 C28 136.6(3) . . . . ?
C9 N6 C23 C28 -46.8(4) . . . . ?
C25 C26 C27 C28 3.2(4) . . . . ?
N8 C26 C27 C28 -174.9(3) . . . . ?
C16 C15 C17 C18 33.9(5) . . . . ?
C14 C15 C17 C18 -145.5(3) . . . . ?
C16 C15 C17 C22 -147.8(3) . . . . ?
C14 C15 C17 C22 32.8(4) . . . . ?
C9 N6 C20 C19 144.9(3) . . . . ?
C23 N6 C20 C19 -38.6(4) . . . . ?
C9 N6 C20 C21 -33.3(4) . . . . ?
C23 N6 C20 C21 143.2(3) . . . . ?
C41 C42 C43 C44 0.1(4) . . . . ?
C45 C42 C43 C44 -179.0(3) . . . . ?
C39 C44 C43 C42 0.5(4) . . . . ?
C34 C44 C43 C42 -176.3(3) . . . . ?
C26 C25 C24 C23 0.7(4) . . . . ?
C28 C23 C24 C25 2.2(4) . . . . ?
N6 C23 C24 C25 -176.1(3) . . . . ?
N7 C13 N5 S2 -179.3(3) . . . . ?
C12 C13 N5 S2 0.2(4) . . . . ?
N4 S2 N5 C13 0.2(3) . . . . ?
C7 C8 C9 C10 0.9(4) . . . . ?
C7 C8 C9 N6 -178.1(3) . . . . ?
C20 N6 C9 C8 141.7(3) . . . . ?
C23 N6 C9 C8 -34.9(4) . . . . ?
C20 N6 C9 C10 -37.2(4) . . . . ?
C23 N6 C9 C10 146.2(3) . . . . ?
C43 C42 C45 C48 -14.3(6) . . . . ?
C41 C42 C45 C48 166.6(5) . . . . ?
C43 C42 C45 C47 109.6(4) . . . . ?
C41 C42 C45 C47 -69.5(4) . . . . ?
C43 C42 C45 C46 -132.3(4) . . . . ?
C41 C42 C45 C46 48.7(4) . . . . ?
C33 C32 C35 C37 122.6(3) . . . . ?
C31 C32 C35 C37 -57.5(4) . . . . ?
C33 C32 C35 C38 0.9(4) . . . . ?
C31 C32 C35 C38 -179.2(3) . . . . ?
C33 C32 C35 C36 -118.7(3) . . . . ?
C31 C32 C35 C36 61.1(4) . . . . ?
C26 C27 C28 C23 -0.3(4) . . . . ?
C24 C23 C28 C27 -2.4(4) . . . . ?
N6 C23 C28 C27 175.9(3) . . . . ?
C5 C4 C6 C11 -141.8(3) . . . . ?
C3 C4 C6 C11 38.2(4) . . . . ?
C5 C4 C6 C7 38.1(4) . . . . ?
C3 C4 C6 C7 -141.9(3) . . . . ?
C3 C4 C5 C1 -0.5(4) . . . . ?
C6 C4 C5 C1 179.5(3) . . . . ?
C9 C8 C7 C6 0.3(4) . . . . ?
C11 C6 C7 C8 -0.7(4) . . . . ?
C4 C6 C7 C8 179.4(3) . . . . ?
C4 C5 C1 N1 179.0(3) . . . . ?
C4 C5 C1 C2 -1.7(4) . . . . ?
C18 C17 C22 C21 1.7(4) . . . . ?
C15 C17 C22 C21 -176.7(3) . . . . ?
C8 C9 C10 C11 -1.6(5) . . . . ?
N6 C9 C10 C11 177.4(3) . . . . ?
C22 C17 C18 C19 -2.8(5) . . . . ?
C15 C17 C18 C19 175.6(3) . . . . ?
C16 C15 C14 N7 -0.6(5) . . . . ?
C17 C15 C14 N7 178.8(3) . . . . ?
C9 C10 C11 C6 1.1(5) . . . . ?
C7 C6 C11 C10 0.0(4) . . . . ?
C4 C6 C11 C10 179.9(3) . . . . ?
C15 C14 N7 C13 0.5(6) . . . . ?
N5 C13 N7 C14 179.2(3) . . . . ?
C12 C13 N7 C14 -0.2(5) . . . . ?
C14 C15 C16 C12 0.3(5) . . . . ?
C17 C15 C16 C12 -179.1(3) . . . . ?
C21 C20 C19 C18 2.0(5) . . . . ?
N6 C20 C19 C18 -176.3(3) . . . . ?
C17 C18 C19 C20 1.0(5) . . . . ?
C32 C31 C30 C29 0.5(5) . . . . ?
N8 C29 C30 C31 177.9(3) . . . . ?
C34 C29 C30 C31 0.9(4) . . . . ?
C15 C16 C12 N4 -178.8(3) . . . . ?
C15 C16 C12 C13 0.0(5) . . . . ?
N5 C13 C12 N4 -0.6(4) . . . . ?
N7 C13 C12 N4 178.9(3) . . . . ?
N5 C13 C12 C16 -179.5(3) . . . . ?
N7 C13 C12 C16 0.0(5) . . . . ?
C16 C12 N4 S2 179.5(3) . . . . ?
C13 C12 N4 S2 0.7(4) . . . . ?
N5 S2 N4 C12 -0.5(3) . . . . ?
C17 C22 C21 C20 1.3(5) . . . . ?
C19 C20 C21 C22 -3.1(5) . . . . ?
N6 C20 C21 C22 175.2(3) . . . . ?
C3 N3 C2 N2 179.8(3) . . . . ?
C3 N3 C2 C1 -0.5(5) . . . . ?
N1 C1 C2 N2 1.6(4) . . . . ?
C5 C1 C2 N2 -177.8(3) . . . . ?
N1 C1 C2 N3 -178.2(3) . . . . ?
C5 C1 C2 N3 2.4(5) . . . . ?
C2 N3 C3 C4 -2.1(5) . . . . ?
C5 C4 C3 N3 2.7(5) . . . . ?
C6 C4 C3 N3 -177.3(3) . . . . ?
C5 C1 N1 S1 178.8(3) . . . . ?
C2 C1 N1 S1 -0.5(4) . . . . ?
N2 S1 N1 C1 -0.5(3) . . . . ?
N3 C2 N2 S1 178.0(3) . . . . ?
C1 C2 N2 S1 -1.8(3) . . . . ?
N1 S1 N2 C2 1.4(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.664
_refine_diff_density_min         -0.356
_refine_diff_density_rms         0.051
