# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 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_a
_database_code_depnum_ccdc_archive 'CCDC 1437142'
_audit_update_record             
;
2015-11-16 deposited with the CCDC.
2016-04-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        DFTCNQ-DPTTA
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C46 H24 F2 N4 S4'
_chemical_formula_weight         798.93

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'
F F 0.0171 0.0103 '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                   7.9146(16)
_cell_length_b                   10.340(2)
_cell_length_c                   11.030(2)
_cell_angle_alpha                89.02(3)
_cell_angle_beta                 80.45(3)
_cell_angle_gamma                82.36(3)
_cell_volume                     882.2(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2805
_cell_measurement_theta_min      1.8723
_cell_measurement_theta_max      27.4767

_exptl_crystal_description       rod
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.504
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             410
_exptl_absorpt_coefficient_mu    0.323
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7160
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  Confocal
_diffrn_measurement_device_type  'MM007HF + CCD (Saturn724+)'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11582
_diffrn_reflns_av_R_equivalents  0.0732
_diffrn_reflns_av_sigmaI/netI    0.0747
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.87
_diffrn_reflns_theta_max         27.49
_reflns_number_total             4029
_reflns_number_gt                3283
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'SHELX-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELX-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
;
 Mercury: visualization and analysis of crystal structures, C. F. Macrae,
 P. R. Edgington, P. McCabe, E. Pidcock, G. P. Shields, R. Taylor,
 M. Towler and J. van de Streek, J. Appl. Cryst., 39, 453-457, 2006.
;
_computing_publication_material  'SHELX-97 (Sheldrick, 2008)'

_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)+(0.0518P)²+0.4374P] 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         4029
_refine_ls_number_parameters     263
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0691
_refine_ls_R_factor_gt           0.0546
_refine_ls_wR_factor_ref         0.1350
_refine_ls_wR_factor_gt          0.1251
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_restrained_S_all      1.088
_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 0.08318(8) 0.79398(6) 0.47977(5) 0.01631(16) Uani 1 1 d . . .
S2 S -0.08725(8) 1.01115(6) 0.32219(5) 0.01564(16) Uani 1 1 d . . .
F1 F 0.36274(19) 0.24944(13) 0.46270(13) 0.0194(4) Uani 0.932(4) 1 d PD A 1
N1 N 0.6458(3) 0.1239(2) 0.8723(2) 0.0264(5) Uani 1 1 d . . .
N2 N 0.7828(3) -0.2805(2) 0.78502(19) 0.0232(5) Uani 1 1 d . . .
C1 C 0.7210(3) -0.1840(2) 0.7497(2) 0.0186(5) Uani 1 1 d . . .
C2 C 0.6472(3) -0.0574(2) 0.7142(2) 0.0159(5) Uani 1 1 d . . .
C3 C 0.6470(3) 0.0439(2) 0.8014(2) 0.0193(5) Uani 1 1 d . . .
C4 C 0.5756(3) -0.0294(2) 0.6085(2) 0.0146(5) Uani 1 1 d . . .
C5 C 0.5032(3) 0.1002(2) 0.5829(2) 0.0156(5) Uani 1 1 d D . .
H5 H 0.5046 0.1674 0.6375 0.019 Uiso 0.932(4) 1 d PR A .
C6 C 0.4329(3) 0.1257(2) 0.4812(2) 0.0168(5) Uani 1 1 d D . .
H1 H 0.3871 0.2114 0.4679 0.020 Uiso 0.068(4) 1 d PR . .
C7 C 0.1792(3) 0.6879(2) 0.5820(2) 0.0154(5) Uani 1 1 d . . .
C8 C 0.2091(3) 0.5606(2) 0.5322(2) 0.0167(5) Uani 1 1 d . . .
H8 H 0.2615 0.4877 0.5724 0.020 Uiso 1 1 calc R . .
C9 C 0.1561(3) 0.5513(2) 0.4206(2) 0.0177(5) Uani 1 1 d . . .
H9 H 0.1697 0.4712 0.3768 0.021 Uiso 1 1 calc R . .
C10 C 0.0802(3) 0.6693(2) 0.3763(2) 0.0147(5) Uani 1 1 d . . .
C11 C 0.0092(3) 0.6751(2) 0.2670(2) 0.0169(5) Uani 1 1 d . . .
H11 H 0.0192 0.5912 0.2307 0.020 Uiso 1 1 calc R . .
C12 C -0.0708(3) 0.7701(2) 0.1988(2) 0.0191(5) Uani 1 1 d . . .
H12 H -0.1022 0.7351 0.1279 0.023 Uiso 1 1 calc R . .
C13 C -0.1174(3) 0.9065(2) 0.2083(2) 0.0160(5) Uani 1 1 d . . .
C14 C -0.1989(3) 0.9794(2) 0.1200(2) 0.0196(5) Uani 1 1 d . . .
H14 H -0.2254 0.9409 0.0491 0.023 Uiso 1 1 calc R . .
C15 C -0.2367(3) 1.1107(2) 0.1447(2) 0.0189(5) Uani 1 1 d . . .
H15 H -0.2921 1.1705 0.0927 0.023 Uiso 1 1 calc R . .
C16 C -0.1862(3) 1.1490(2) 0.2536(2) 0.0154(5) Uani 1 1 d . . .
C17 C -0.2140(3) 1.2759(2) 0.3036(2) 0.0156(5) Uani 1 1 d . . .
C18 C -0.2796(3) 1.3833(2) 0.2238(2) 0.0165(5) Uani 1 1 d . . .
C19 C -0.4348(3) 1.4637(2) 0.2607(2) 0.0191(5) Uani 1 1 d . . .
H19 H -0.5046 1.4481 0.3369 0.023 Uiso 1 1 calc R . .
C20 C -0.4886(3) 1.5658(2) 0.1874(2) 0.0208(5) Uani 1 1 d . . .
H20 H -0.5935 1.6211 0.2145 0.025 Uiso 1 1 calc R . .
C21 C -0.3899(3) 1.5879(2) 0.0747(2) 0.0200(5) Uani 1 1 d . . .
H21 H -0.4271 1.6579 0.0244 0.024 Uiso 1 1 calc R . .
C22 C -0.2372(3) 1.5074(2) 0.0361(2) 0.0191(5) Uani 1 1 d . . .
H22 H -0.1698 1.5216 -0.0415 0.023 Uiso 1 1 calc R . .
C23 C -0.1816(3) 1.4060(2) 0.1100(2) 0.0178(5) Uani 1 1 d . . .
H23 H -0.0761 1.3516 0.0829 0.021 Uiso 1 1 calc R . .
F1A F 0.497(2) 0.2124(14) 0.6418(16) 0.013(5) Uani 0.068(4) 1 d PD 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 C10 1.742(2) . ?
S1 C7 1.753(2) . ?
S2 C13 1.738(2) . ?
S2 C16 1.755(2) . ?
F1 C6 1.351(3) . ?
F1 H1 0.4218 . ?
N1 C3 1.146(3) . ?
N2 C1 1.143(3) . ?
C1 C2 1.436(3) . ?
C2 C4 1.388(3) . ?
C2 C3 1.434(3) . ?
C4 C5 1.429(3) . ?
C4 C6 1.431(3) 2_656 ?
C5 F1A 1.331(13) . ?
C5 C6 1.340(3) . ?
C5 H5 0.9299 . ?
C6 C4 1.431(3) 2_656 ?
C6 H1 0.9300 . ?
C7 C17 1.402(3) 2_576 ?
C7 C8 1.410(3) . ?
C8 C9 1.374(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.404(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.409(3) . ?
C11 C12 1.378(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.411(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.410(3) . ?
C14 C15 1.373(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.405(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.408(3) . ?
C17 C7 1.402(3) 2_576 ?
C17 C18 1.498(3) . ?
C18 C19 1.392(3) . ?
C18 C23 1.396(3) . ?
C19 C20 1.384(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.387(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.382(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.387(3) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
F1A H5 0.4638 . ?

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
C10 S1 C7 93.17(11) . . ?
C13 S2 C16 93.01(12) . . ?
C6 F1 H1 2.9 . . ?
N2 C1 C2 175.0(3) . . ?
C4 C2 C3 120.3(2) . . ?
C4 C2 C1 125.8(2) . . ?
C3 C2 C1 113.9(2) . . ?
N1 C3 C2 179.1(3) . . ?
C2 C4 C5 121.2(2) . . ?
C2 C4 C6 123.5(2) . 2_656 ?
C5 C4 C6 115.3(2) . 2_656 ?
F1A C5 C6 108.1(8) . . ?
F1A C5 C4 131.2(9) . . ?
C6 C5 C4 120.6(2) . . ?
F1A C5 H5 12.0 . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.6 . . ?
C5 C6 F1 118.3(2) . . ?
C5 C6 C4 124.0(2) . 2_656 ?
F1 C6 C4 117.7(2) . 2_656 ?
C5 C6 H1 117.9 . . ?
F1 C6 H1 1.3 . . ?
C4 C6 H1 118.0 2_656 . ?
C17 C7 C8 126.1(2) 2_576 . ?
C17 C7 S1 125.07(18) 2_576 . ?
C8 C7 S1 108.80(18) . . ?
C9 C8 C7 114.2(2) . . ?
C9 C8 H8 122.9 . . ?
C7 C8 H8 122.9 . . ?
C8 C9 C10 114.7(2) . . ?
C8 C9 H9 122.6 . . ?
C10 C9 H9 122.6 . . ?
C9 C10 C11 121.9(2) . . ?
C9 C10 S1 109.10(18) . . ?
C11 C10 S1 128.98(18) . . ?
C12 C11 C10 137.0(2) . . ?
C12 C11 H11 111.5 . . ?
C10 C11 H11 111.5 . . ?
C11 C12 C13 135.7(2) . . ?
C11 C12 H12 112.1 . . ?
C13 C12 H12 112.1 . . ?
C14 C13 C12 122.5(2) . . ?
C14 C13 S2 109.19(18) . . ?
C12 C13 S2 128.32(19) . . ?
C15 C14 C13 114.6(2) . . ?
C15 C14 H14 122.7 . . ?
C13 C14 H14 122.7 . . ?
C14 C15 C16 114.2(2) . . ?
C14 C15 H15 122.9 . . ?
C16 C15 H15 122.9 . . ?
C15 C16 C17 126.5(2) . . ?
C15 C16 S2 109.04(18) . . ?
C17 C16 S2 124.47(18) . . ?
C7 C17 C16 126.5(2) 2_576 . ?
C7 C17 C18 117.0(2) 2_576 . ?
C16 C17 C18 116.4(2) . . ?
C19 C18 C23 118.5(2) . . ?
C19 C18 C17 122.0(2) . . ?
C23 C18 C17 119.5(2) . . ?
C20 C19 C18 120.7(2) . . ?
C20 C19 H19 119.6 . . ?
C18 C19 H19 119.6 . . ?
C19 C20 C21 120.3(2) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 H20 119.9 . . ?
C22 C21 C20 119.5(2) . . ?
C22 C21 H21 120.2 . . ?
C20 C21 H21 120.2 . . ?
C21 C22 C23 120.4(2) . . ?
C21 C22 H22 119.8 . . ?
C23 C22 H22 119.8 . . ?
C22 C23 C18 120.5(2) . . ?
C22 C23 H23 119.7 . . ?
C18 C23 H23 119.7 . . ?
C5 F1A H5 24.7 . . ?

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
N2 C1 C2 C4 176(3) . . . . ?
N2 C1 C2 C3 -6(3) . . . . ?
C4 C2 C3 N1 125(18) . . . . ?
C1 C2 C3 N1 -53(18) . . . . ?
C3 C2 C4 C5 1.1(3) . . . . ?
C1 C2 C4 C5 179.1(2) . . . . ?
C3 C2 C4 C6 -178.4(2) . . . 2_656 ?
C1 C2 C4 C6 -0.4(4) . . . 2_656 ?
C2 C4 C5 F1A 4.4(11) . . . . ?
C6 C4 C5 F1A -176.1(11) 2_656 . . . ?
C2 C4 C5 C6 -179.3(2) . . . . ?
C6 C4 C5 C6 0.2(4) 2_656 . . . ?
F1A C5 C6 F1 -4.4(9) . . . . ?
C4 C5 C6 F1 178.55(19) . . . . ?
F1A C5 C6 C4 176.8(9) . . . 2_656 ?
C4 C5 C6 C4 -0.2(4) . . . 2_656 ?
C10 S1 C7 C17 -176.7(2) . . . 2_576 ?
C10 S1 C7 C8 1.20(18) . . . . ?
C17 C7 C8 C9 177.2(2) 2_576 . . . ?
S1 C7 C8 C9 -0.6(3) . . . . ?
C7 C8 C9 C10 -0.5(3) . . . . ?
C8 C9 C10 C11 -176.0(2) . . . . ?
C8 C9 C10 S1 1.4(3) . . . . ?
C7 S1 C10 C9 -1.49(18) . . . . ?
C7 S1 C10 C11 175.7(2) . . . . ?
C9 C10 C11 C12 -179.4(3) . . . . ?
S1 C10 C11 C12 3.8(4) . . . . ?
C10 C11 C12 C13 0.2(5) . . . . ?
C11 C12 C13 C14 179.1(3) . . . . ?
C11 C12 C13 S2 -0.5(4) . . . . ?
C16 S2 C13 C14 1.12(19) . . . . ?
C16 S2 C13 C12 -179.3(2) . . . . ?
C12 C13 C14 C15 179.3(2) . . . . ?
S2 C13 C14 C15 -1.1(3) . . . . ?
C13 C14 C15 C16 0.4(3) . . . . ?
C14 C15 C16 C17 -177.6(2) . . . . ?
C14 C15 C16 S2 0.5(3) . . . . ?
C13 S2 C16 C15 -0.93(18) . . . . ?
C13 S2 C16 C17 177.2(2) . . . . ?
C15 C16 C17 C7 173.3(2) . . . 2_576 ?
S2 C16 C17 C7 -4.6(4) . . . 2_576 ?
C15 C16 C17 C18 -9.7(4) . . . . ?
S2 C16 C17 C18 172.41(17) . . . . ?
C7 C17 C18 C19 -61.4(3) 2_576 . . . ?
C16 C17 C18 C19 121.2(3) . . . . ?
C7 C17 C18 C23 117.3(3) 2_576 . . . ?
C16 C17 C18 C23 -60.0(3) . . . . ?
C23 C18 C19 C20 -1.6(4) . . . . ?
C17 C18 C19 C20 177.1(2) . . . . ?
C18 C19 C20 C21 1.4(4) . . . . ?
C19 C20 C21 C22 -0.2(4) . . . . ?
C20 C21 C22 C23 -0.7(4) . . . . ?
C21 C22 C23 C18 0.4(4) . . . . ?
C19 C18 C23 C22 0.8(4) . . . . ?
C17 C18 C23 C22 -178.1(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.375
_refine_diff_density_min         -0.411
_refine_diff_density_rms         0.082
####################################################################### 
# 
# 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_sa2870
_database_code_depnum_ccdc_archive 'CCDC 1437143'
_audit_update_record             
;
2015-11-16 deposited with the CCDC.
2016-04-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        SNTCNQ-DPTTA
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C34 H22 S4, C12 H2 N6 S'
_chemical_formula_sum            'C46 H24 N6 S5'
_chemical_formula_weight         821.01

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                   7.7712(16)
_cell_length_b                   11.266(2)
_cell_length_c                   11.337(2)
_cell_angle_alpha                74.094(8)
_cell_angle_beta                 78.856(9)
_cell_angle_gamma                80.050(9)
_cell_volume                     928.9(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3348
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      27.48

_exptl_crystal_description       rod
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.468
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             422
_exptl_absorpt_coefficient_mu    0.358
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5622
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'


_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12106
_diffrn_reflns_av_R_equivalents  0.0458
_diffrn_reflns_av_sigmaI/netI    0.0405
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.69
_diffrn_reflns_theta_max         27.50
_reflns_number_total             4247
_reflns_number_gt                4042
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'Olex2 ver 1.1'
_computing_molecular_graphics    'Olex2 ver 1.1'
_computing_publication_material  'SHELX97 (Sheldrick, 2008)'


_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)+(0.0415P)²+0.5985P] 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         4247
_refine_ls_number_parameters     290
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0520
_refine_ls_R_factor_gt           0.0489
_refine_ls_wR_factor_ref         0.1154
_refine_ls_wR_factor_gt          0.1133
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_restrained_S_all      1.111
_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 0.43249(7) 1.02898(4) 0.18205(4) 0.02930(14) Uani 1 1 d . . .
S2 S 0.39412(6) 0.82026(4) 0.07670(4) 0.02693(13) Uani 1 1 d . . .
S3 S 0.07027(14) 0.89429(9) 0.73502(9) 0.0331(2) Uani 0.50 1 d P A 1
N1 N 0.1129(4) 1.0206(3) 0.7599(3) 0.0312(7) Uani 0.50 1 d P A 1
N2 N -0.0161(4) 0.8261(3) 0.8722(3) 0.0293(7) Uani 0.50 1 d P A 1
N3 N -0.1887(4) 0.6130(3) 1.0202(3) 0.0950(12) Uani 1 1 d . A .
N4 N -0.2733(3) 0.7289(2) 1.3602(3) 0.0660(7) Uani 1 1 d . A .
C1 C 0.5190(3) 1.2552(2) 0.2088(2) 0.0363(5) Uani 1 1 d . . .
H1 H 0.5108 1.2981 0.2715 0.044 Uiso 1 1 calc R . .
C2 C 0.4508(3) 1.14125(18) 0.25736(18) 0.0298(4) Uani 1 1 d . . .
C3 C 0.3845(3) 1.0992(2) 0.38504(19) 0.0346(4) Uani 1 1 d . . .
H3 H 0.3818 1.1463 0.4434 0.042 Uiso 1 1 calc R . .
C4 C 0.3248(3) 0.98567(19) 0.41796(18) 0.0325(4) Uani 1 1 d . . .
H4 H 0.2771 0.9477 0.5008 0.039 Uiso 1 1 calc R . .
C5 C 0.3397(2) 0.92949(18) 0.31910(17) 0.0281(4) Uani 1 1 d . . .
C6 C 0.2926(2) 0.81202(18) 0.32851(17) 0.0283(4) Uani 1 1 d . B .
C7 C 0.3071(2) 0.75440(17) 0.23126(17) 0.0277(4) Uani 1 1 d . . .
C8 C 0.2558(3) 0.63832(19) 0.23891(19) 0.0331(4) Uani 1 1 d . . .
H8 H 0.2048 0.5869 0.3145 0.040 Uiso 1 1 calc R . .
C9 C 0.2859(3) 0.60575(19) 0.1279(2) 0.0346(4) Uani 1 1 d . . .
H9 H 0.2572 0.5298 0.1202 0.041 Uiso 1 1 calc R . .
C10 C 0.3627(3) 0.69414(18) 0.02612(19) 0.0299(4) Uani 1 1 d . . .
C11 C 0.4052(3) 0.67758(19) -0.0950(2) 0.0359(5) Uani 1 1 d . . .
H11 H 0.3741 0.6013 -0.0999 0.043 Uiso 1 1 calc R . .
C12 C 0.2247(3) 0.73813(19) 0.45654(18) 0.0315(4) Uani 1 1 d . . .
C13 C 0.3360(3) 0.64619(19) 0.5235(2) 0.0359(5) Uani 1 1 d . B .
H13 H 0.4557 0.6288 0.4877 0.043 Uiso 1 1 calc R . .
C14 C 0.2756(3) 0.5790(2) 0.6419(2) 0.0377(5) Uani 1 1 d . . .
H14 H 0.3547 0.5167 0.6866 0.045 Uiso 1 1 calc R B .
C15 C 0.1044(4) 0.6010(2) 0.6953(2) 0.0512(6) Uani 1 1 d . B .
H15 H 0.0684 0.5688 0.7816 0.061 Uiso 0.57(2) 1 calc PR B 1
H15A H 0.0509 0.5417 0.7632 0.061 Uiso 0.43(2) 1 calc PR B 2
C16 C -0.0198(9) 0.6744(6) 0.6168(8) 0.0437(19) Uani 0.57(2) 1 d P B 1
H16 H -0.1434 0.6755 0.6447 0.052 Uiso 0.57(2) 1 calc PR B 1
C17 C 0.0434(9) 0.7443(7) 0.4990(8) 0.0375(14) Uani 0.57(2) 1 d P B 1
H17 H -0.0373 0.7961 0.4475 0.045 Uiso 0.57(2) 1 calc PR B 1
C18 C 0.0642(3) 1.02052(19) 0.8722(2) 0.0325(4) Uani 1 1 d . . .
H18 H 0.1071 1.0337 0.7849 0.039 Uiso 0.50 1 d PR A 2
C19 C -0.0096(3) 0.9122(2) 0.9346(2) 0.0366(5) Uani 1 1 d . A .
H19 H -0.0153 0.8528 0.8893 0.044 Uiso 0.50 1 d PR C 2
C20 C -0.0785(3) 0.88595(19) 1.0664(2) 0.0338(4) Uani 1 1 d . . .
C21 C -0.1540(3) 0.7802(2) 1.1268(2) 0.0393(5) Uani 1 1 d . A .
C22 C -0.1716(3) 0.6880(2) 1.0654(3) 0.0561(7) Uani 1 1 d . . .
C23 C -0.2205(3) 0.7530(2) 1.2570(3) 0.0439(6) Uani 1 1 d . . .
C16A C 0.0130(12) 0.7147(14) 0.6449(7) 0.047(3) Uani 0.43(2) 1 d P B 2
H16A H -0.0882 0.7475 0.6935 0.057 Uiso 0.43(2) 1 calc PR B 2
C17A C 0.0663(12) 0.7820(14) 0.5244(8) 0.042(2) Uani 0.43(2) 1 d P B 2
H17A H -0.0032 0.8564 0.4884 0.050 Uiso 0.43(2) 1 calc PR B 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 C2 1.7464(19) . ?
S1 C5 1.755(2) . ?
S2 C10 1.7400(19) . ?
S2 C7 1.7551(19) . ?
S3 N2 1.606(3) . ?
S3 N1 1.623(3) . ?
S3 C19 2.282(2) . ?
S3 H19 1.7117 . ?
N1 C18 1.255(4) . ?
N1 H18 0.3456 . ?
N2 C19 1.360(4) . ?
N2 H19 0.4008 . ?
N3 C22 1.139(3) . ?
N4 C23 1.136(3) . ?
C1 C11 1.382(3) 2_675 ?
C1 C2 1.403(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.416(3) . ?
C3 C4 1.367(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.408(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.404(3) . ?
C6 C7 1.403(3) . ?
C6 C12 1.507(3) . ?
C7 C8 1.407(3) . ?
C8 C9 1.372(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.410(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.405(3) . ?
C11 C1 1.382(3) 2_675 ?
C11 H11 0.9500 . ?
C12 C13 1.382(3) . ?
C12 C17 1.394(6) . ?
C12 C17A 1.409(9) . ?
C13 C14 1.385(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.362(3) . ?
C14 H14 0.9500 . ?
C15 C16A 1.383(11) . ?
C15 C16 1.435(9) . ?
C15 H15 0.9500 . ?
C15 H15A 0.9500 . ?
C16 C17 1.396(8) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C19 1.389(3) . ?
C18 C20 1.443(3) 2_577 ?
C18 H18 0.9600 . ?
C19 C20 1.452(3) . ?
C19 H19 0.9598 . ?
C20 C21 1.367(3) . ?
C20 C18 1.443(3) 2_577 ?
C21 C23 1.433(4) . ?
C21 C22 1.437(3) . ?
C16A C17A 1.390(11) . ?
C16A H16A 0.9500 . ?
C17A H17A 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
C2 S1 C5 93.34(9) . . ?
C10 S2 C7 93.04(9) . . ?
N2 S3 N1 100.50(17) . . ?
N2 S3 C19 35.90(13) . . ?
N1 S3 C19 64.61(13) . . ?
N2 S3 H19 13.4 . . ?
N1 S3 H19 87.1 . . ?
C19 S3 H19 22.5 . . ?
C18 N1 S3 109.9(2) . . ?
C18 N1 H18 27.0 . . ?
S3 N1 H18 136.9 . . ?
C19 N2 S3 100.3(2) . . ?
C19 N2 H19 2.8 . . ?
S3 N2 H19 98.6 . . ?
C11 C1 C2 137.59(19) 2_675 . ?
C11 C1 H1 111.2 2_675 . ?
C2 C1 H1 111.2 . . ?
C1 C2 C3 121.96(18) . . ?
C1 C2 S1 129.52(16) . . ?
C3 C2 S1 108.51(15) . . ?
C4 C3 C2 114.87(18) . . ?
C4 C3 H3 122.6 . . ?
C2 C3 H3 122.6 . . ?
C3 C4 C5 114.55(18) . . ?
C3 C4 H4 122.7 . . ?
C5 C4 H4 122.7 . . ?
C6 C5 C4 125.87(18) . . ?
C6 C5 S1 125.40(15) . . ?
C4 C5 S1 108.72(15) . . ?
C7 C6 C5 126.66(18) . . ?
C7 C6 C12 116.37(17) . . ?
C5 C6 C12 116.93(17) . . ?
C6 C7 C8 127.20(18) . . ?
C6 C7 S2 123.82(15) . . ?
C8 C7 S2 108.99(15) . . ?
C9 C8 C7 114.25(18) . . ?
C9 C8 H8 122.9 . . ?
C7 C8 H8 122.9 . . ?
C8 C9 C10 114.53(18) . . ?
C8 C9 H9 122.7 . . ?
C10 C9 H9 122.7 . . ?
C11 C10 C9 123.21(18) . . ?
C11 C10 S2 127.59(16) . . ?
C9 C10 S2 109.19(15) . . ?
C1 C11 C10 135.79(19) 2_675 . ?
C1 C11 H11 112.1 2_675 . ?
C10 C11 H11 112.1 . . ?
C13 C12 C17 118.2(3) . . ?
C13 C12 C17A 116.4(4) . . ?
C17 C12 C17A 26.3(4) . . ?
C13 C12 C6 120.52(18) . . ?
C17 C12 C6 120.1(3) . . ?
C17A C12 C6 120.7(4) . . ?
C12 C13 C14 121.0(2) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 H13 119.5 . . ?
C15 C14 C13 120.9(2) . . ?
C15 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C14 C15 C16A 116.2(4) . . ?
C14 C15 C16 117.9(3) . . ?
C16A C15 C16 29.6(4) . . ?
C14 C15 H15 121.1 . . ?
C16A C15 H15 114.5 . . ?
C16 C15 H15 121.1 . . ?
C14 C15 H15A 121.9 . . ?
C16A C15 H15A 121.9 . . ?
C16 C15 H15A 112.3 . . ?
H15 C15 H15A 28.3 . . ?
C17 C16 C15 119.1(5) . . ?
C17 C16 H16 120.5 . . ?
C15 C16 H16 120.5 . . ?
C12 C17 C16 120.2(5) . . ?
C12 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
N1 C18 C19 109.5(2) . . ?
N1 C18 C20 128.1(2) . 2_577 ?
C19 C18 C20 122.4(2) . 2_577 ?
N1 C18 H18 9.4 . . ?
C19 C18 H18 118.9 . . ?
C20 C18 H18 118.7 2_577 . ?
N2 C19 C18 119.8(2) . . ?
N2 C19 C20 118.1(2) . . ?
C18 C19 C20 122.09(18) . . ?
N2 C19 S3 43.80(15) . . ?
C18 C19 S3 75.98(14) . . ?
C20 C19 S3 161.93(16) . . ?
N2 C19 H19 1.2 . . ?
C18 C19 H19 119.1 . . ?
C20 C19 H19 118.8 . . ?
S3 C19 H19 43.1 . . ?
C21 C20 C18 122.7(2) . 2_577 ?
C21 C20 C19 121.8(2) . . ?
C18 C20 C19 115.48(19) 2_577 . ?
C20 C21 C23 122.1(2) . . ?
C20 C21 C22 122.9(2) . . ?
C23 C21 C22 114.9(2) . . ?
N3 C22 C21 177.8(4) . . ?
N4 C23 C21 178.6(2) . . ?
C15 C16A C17A 121.3(6) . . ?
C15 C16A H16A 119.4 . . ?
C17A C16A H16A 119.4 . . ?
C16A C17A C12 119.1(7) . . ?
C16A C17A H17A 120.5 . . ?
C12 C17A H17A 120.5 . . ?

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
N2 S3 N1 C18 -0.5(3) . . . . ?
C19 S3 N1 C18 0.16(19) . . . . ?
N1 S3 N2 C19 1.0(2) . . . . ?
C11 C1 C2 C3 178.4(2) 2_675 . . . ?
C11 C1 C2 S1 -0.8(4) 2_675 . . . ?
C5 S1 C2 C1 179.0(2) . . . . ?
C5 S1 C2 C3 -0.25(15) . . . . ?
C1 C2 C3 C4 -179.2(2) . . . . ?
S1 C2 C3 C4 0.1(2) . . . . ?
C2 C3 C4 C5 0.2(3) . . . . ?
C3 C4 C5 C6 178.21(19) . . . . ?
C3 C4 C5 S1 -0.3(2) . . . . ?
C2 S1 C5 C6 -178.22(18) . . . . ?
C2 S1 C5 C4 0.33(15) . . . . ?
C4 C5 C6 C7 -179.73(19) . . . . ?
S1 C5 C6 C7 -1.4(3) . . . . ?
C4 C5 C6 C12 -1.8(3) . . . . ?
S1 C5 C6 C12 176.48(14) . . . . ?
C5 C6 C7 C8 -178.10(19) . . . . ?
C12 C6 C7 C8 4.0(3) . . . . ?
C5 C6 C7 S2 1.5(3) . . . . ?
C12 C6 C7 S2 -176.44(14) . . . . ?
C10 S2 C7 C6 179.99(17) . . . . ?
C10 S2 C7 C8 -0.37(15) . . . . ?
C6 C7 C8 C9 179.88(19) . . . . ?
S2 C7 C8 C9 0.3(2) . . . . ?
C7 C8 C9 C10 0.0(3) . . . . ?
C8 C9 C10 C11 179.4(2) . . . . ?
C8 C9 C10 S2 -0.3(2) . . . . ?
C7 S2 C10 C11 -179.3(2) . . . . ?
C7 S2 C10 C9 0.40(16) . . . . ?
C9 C10 C11 C1 -178.9(2) . . . 2_675 ?
S2 C10 C11 C1 0.8(4) . . . 2_675 ?
C7 C6 C12 C13 79.8(2) . . . . ?
C5 C6 C12 C13 -98.3(2) . . . . ?
C7 C6 C12 C17 -87.6(6) . . . . ?
C5 C6 C12 C17 94.3(6) . . . . ?
C7 C6 C12 C17A -118.2(8) . . . . ?
C5 C6 C12 C17A 63.7(9) . . . . ?
C17 C12 C13 C14 -13.3(6) . . . . ?
C17A C12 C13 C14 16.3(9) . . . . ?
C6 C12 C13 C14 179.06(19) . . . . ?
C12 C13 C14 C15 0.5(3) . . . . ?
C13 C14 C15 C16A -19.6(9) . . . . ?
C13 C14 C15 C16 13.7(6) . . . . ?
C14 C15 C16 C17 -15.3(8) . . . . ?
C16A C15 C16 C17 79.3(9) . . . . ?
C13 C12 C17 C16 11.3(7) . . . . ?
C17A C12 C17 C16 -81.7(14) . . . . ?
C6 C12 C17 C16 179.0(4) . . . . ?
C15 C16 C17 C12 2.8(7) . . . . ?
S3 N1 C18 C19 -0.2(3) . . . . ?
S3 N1 C18 C20 179.49(18) . . . 2_577 ?
S3 N2 C19 C18 -1.4(3) . . . . ?
S3 N2 C19 C20 179.61(16) . . . . ?
N1 C18 C19 N2 1.2(3) . . . . ?
C20 C18 C19 N2 -178.6(2) 2_577 . . . ?
N1 C18 C19 C20 -179.9(2) . . . . ?
C20 C18 C19 C20 0.4(3) 2_577 . . . ?
N1 C18 C19 S3 0.2(2) . . . . ?
C20 C18 C19 S3 -179.59(19) 2_577 . . . ?
N1 S3 C19 N2 -178.9(3) . . . . ?
N2 S3 C19 C18 178.7(3) . . . . ?
N1 S3 C19 C18 -0.14(17) . . . . ?
N2 S3 C19 C20 -1.1(5) . . . . ?
N1 S3 C19 C20 -180.0(5) . . . . ?
N2 C19 C20 C21 -2.3(3) . . . . ?
C18 C19 C20 C21 178.76(19) . . . . ?
S3 C19 C20 C21 -1.4(6) . . . . ?
N2 C19 C20 C18 178.6(2) . . . 2_577 ?
C18 C19 C20 C18 -0.3(3) . . . 2_577 ?
S3 C19 C20 C18 179.5(4) . . . 2_577 ?
C18 C20 C21 C23 -1.6(3) 2_577 . . . ?
C19 C20 C21 C23 179.33(19) . . . . ?
C18 C20 C21 C22 178.8(2) 2_577 . . . ?
C19 C20 C21 C22 -0.3(3) . . . . ?
C20 C21 C22 N3 -174(7) . . . . ?
C23 C21 C22 N3 7(7) . . . . ?
C20 C21 C23 N4 -162(11) . . . . ?
C22 C21 C23 N4 18(11) . . . . ?
C14 C15 C16A C17A 22.1(11) . . . . ?
C16 C15 C16A C17A -78.9(10) . . . . ?
C15 C16A C17A C12 -5.4(11) . . . . ?
C13 C12 C17A C16A -13.8(11) . . . . ?
C17 C12 C17A C16A 87.0(16) . . . . ?
C6 C12 C17A C16A -176.5(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.591
_refine_diff_density_min         -0.425
_refine_diff_density_rms         0.057
####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 1437144'
_audit_update_record             
;
2015-11-16 deposited with the CCDC.
2016-04-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        TFTCNQ-DPTTA
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C46 H22 F4 N4 S4'
_chemical_formula_weight         834.92

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'
F F 0.0171 0.0103 '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                   7.9463(16)
_cell_length_b                   10.099(2)
_cell_length_c                   11.251(2)
_cell_angle_alpha                88.15(3)
_cell_angle_beta                 81.09(3)
_cell_angle_gamma                82.60(3)
_cell_volume                     884.5(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2627
_cell_measurement_theta_min      1.8323
_cell_measurement_theta_max      27.4625

_exptl_crystal_description       rod
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.567
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             426
_exptl_absorpt_coefficient_mu    0.334
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6057
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  Confocal
_diffrn_measurement_device_type  'MM007HF + CCD (Saturn724+)'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12225
_diffrn_reflns_av_R_equivalents  0.0871
_diffrn_reflns_av_sigmaI/netI    0.0801
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.83
_diffrn_reflns_theta_max         27.48
_reflns_number_total             4042
_reflns_number_gt                3349
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'SHELX-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELX-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
;
 Mercury: visualization and analysis of crystal structures, C. F. Macrae,
 P. R. Edgington, P. McCabe, E. Pidcock, G. P. Shields, R. Taylor,
 M. Towler and J. van de Streek, J. Appl. Cryst., 39, 453-457, 2006.
;
_computing_publication_material  'SHELX-97 (Sheldrick, 2008)'

_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)+(0.0976P)²+0.7539P] 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         4042
_refine_ls_number_parameters     262
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0967
_refine_ls_R_factor_gt           0.0821
_refine_ls_wR_factor_ref         0.2124
_refine_ls_wR_factor_gt          0.1990
_refine_ls_goodness_of_fit_ref   1.135
_refine_ls_restrained_S_all      1.135
_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 0.40836(11) 0.20893(9) 0.01663(7) 0.0234(3) Uani 1 1 d . . .
S2 S 0.58320(11) -0.00641(9) 0.17655(7) 0.0234(2) Uani 1 1 d . . .
F1 F 0.0045(3) 0.7974(2) -0.15275(17) 0.0268(5) Uani 1 1 d . . .
F2 F 0.1385(3) 0.7465(2) 0.04249(17) 0.0272(5) Uani 1 1 d . . .
N1 N -0.1521(5) 0.8875(3) -0.3814(3) 0.0368(8) Uani 1 1 d . . .
N2 N -0.2920(4) 1.2860(3) -0.2793(3) 0.0303(7) Uani 1 1 d . . .
C1 C 0.0702(4) 0.8733(3) 0.0239(3) 0.0236(7) Uani 1 1 d . . .
C2 C 0.0002(4) 0.9000(3) -0.0784(3) 0.0218(7) Uani 1 1 d . . .
C3 C -0.0747(4) 1.0288(3) -0.1099(3) 0.0207(7) Uani 1 1 d . . .
C4 C -0.2246(4) 1.1865(4) -0.2481(3) 0.0238(7) Uani 1 1 d . . .
C5 C -0.1457(4) 1.0580(3) -0.2172(3) 0.0233(7) Uani 1 1 d . . .
C6 C -0.1461(5) 0.9593(4) -0.3060(3) 0.0268(8) Uani 1 1 d . . .
C7 C 0.3154(4) 0.3154(3) -0.0869(3) 0.0225(7) Uani 1 1 d . . .
C8 C 0.2819(4) 0.4462(4) -0.0427(3) 0.0233(7) Uani 1 1 d . . .
H8 H 0.2309 0.5195 -0.0854 0.028 Uiso 1 1 calc R . .
C9 C 0.3302(4) 0.4579(4) 0.0684(3) 0.0231(7) Uani 1 1 d . . .
H9 H 0.3141 0.5401 0.1098 0.028 Uiso 1 1 calc R . .
C10 C 0.4054(4) 0.3380(3) 0.1155(3) 0.0210(7) Uani 1 1 d . . .
C11 C 0.4740(5) 0.3360(4) 0.2251(3) 0.0254(7) Uani 1 1 d . . .
H11 H 0.4586 0.4220 0.2598 0.030 Uiso 1 1 calc R . .
C12 C 0.5565(5) 0.2417(4) 0.2935(3) 0.0251(7) Uani 1 1 d . . .
H12 H 0.5854 0.2789 0.3630 0.030 Uiso 1 1 calc R . .
C13 C 0.6097(4) 0.1017(4) 0.2860(3) 0.0244(7) Uani 1 1 d . . .
C14 C 0.6935(5) 0.0309(4) 0.3735(3) 0.0271(8) Uani 1 1 d . . .
H14 H 0.7198 0.0724 0.4418 0.032 Uiso 1 1 calc R . .
C15 C 0.7350(5) -0.1038(4) 0.3528(3) 0.0266(8) Uani 1 1 d . . .
H15 H 0.7919 -0.1635 0.4050 0.032 Uiso 1 1 calc R . .
C16 C 0.6844(4) -0.1443(3) 0.2463(3) 0.0232(7) Uani 1 1 d . . .
C17 C 0.7150(4) -0.2753(3) 0.2008(3) 0.0216(7) Uani 1 1 d . . .
C18 C 0.7797(4) -0.3832(3) 0.2821(3) 0.0226(7) Uani 1 1 d . . .
C19 C 0.6813(5) -0.4051(4) 0.3940(3) 0.0251(7) Uani 1 1 d . . .
H19 H 0.5770 -0.3489 0.4185 0.030 Uiso 1 1 calc R . .
C20 C 0.7350(4) -0.5079(4) 0.4689(3) 0.0259(7) Uani 1 1 d . . .
H20 H 0.6674 -0.5222 0.5445 0.031 Uiso 1 1 calc R . .
C21 C 0.8881(5) -0.5906(4) 0.4341(3) 0.0266(8) Uani 1 1 d . . .
H21 H 0.9242 -0.6617 0.4854 0.032 Uiso 1 1 calc R . .
C22 C 0.9868(4) -0.5690(4) 0.3252(3) 0.0254(7) Uani 1 1 d . . .
H22 H 1.0914 -0.6250 0.3015 0.030 Uiso 1 1 calc R . .
C23 C 0.9342(4) -0.4656(4) 0.2501(3) 0.0257(7) Uani 1 1 d . . .
H23 H 1.0042 -0.4506 0.1757 0.031 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 C10 1.737(3) . ?
S1 C7 1.744(3) . ?
S2 C13 1.726(3) . ?
S2 C16 1.742(3) . ?
F1 C2 1.346(4) . ?
F2 C1 1.348(4) . ?
N1 C6 1.144(5) . ?
N2 C4 1.148(5) . ?
C1 C2 1.359(5) . ?
C1 C3 1.414(5) 2_575 ?
C2 C3 1.416(5) . ?
C3 C1 1.414(5) 2_575 ?
C3 C5 1.417(4) . ?
C4 C5 1.424(5) . ?
C5 C6 1.434(5) . ?
C7 C8 1.405(5) . ?
C7 C17 1.421(5) 2_655 ?
C8 C9 1.376(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.405(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.421(5) . ?
C11 C12 1.370(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.424(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.400(5) . ?
C14 C15 1.376(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.410(5) . ?
C15 H15 0.9500 . ?
C16 C17 1.412(5) . ?
C17 C7 1.421(5) 2_655 ?
C17 C18 1.492(5) . ?
C18 C23 1.396(5) . ?
C18 C19 1.403(5) . ?
C19 C20 1.383(5) . ?
C19 H19 0.9500 . ?
C20 C21 1.394(5) . ?
C20 H20 0.9500 . ?
C21 C22 1.376(5) . ?
C21 H21 0.9500 . ?
C22 C23 1.385(5) . ?
C22 H22 0.9500 . ?
C23 H23 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
C10 S1 C7 92.59(16) . . ?
C13 S2 C16 93.02(17) . . ?
F2 C1 C2 117.4(3) . . ?
F2 C1 C3 119.3(3) . 2_575 ?
C2 C1 C3 123.3(3) . 2_575 ?
F1 C2 C1 117.2(3) . . ?
F1 C2 C3 119.3(3) . . ?
C1 C2 C3 123.5(3) . . ?
C1 C3 C2 113.2(3) 2_575 . ?
C1 C3 C5 122.9(3) 2_575 . ?
C2 C3 C5 123.9(3) . . ?
N2 C4 C5 175.4(4) . . ?
C3 C5 C4 124.1(3) . . ?
C3 C5 C6 122.9(3) . . ?
C4 C5 C6 113.0(3) . . ?
N1 C6 C5 175.2(4) . . ?
C8 C7 C17 125.6(3) . 2_655 ?
C8 C7 S1 109.9(3) . . ?
C17 C7 S1 124.4(3) 2_655 . ?
C9 C8 C7 113.4(3) . . ?
C9 C8 H8 123.3 . . ?
C7 C8 H8 123.3 . . ?
C8 C9 C10 114.5(3) . . ?
C8 C9 H9 122.8 . . ?
C10 C9 H9 122.8 . . ?
C9 C10 C11 121.0(3) . . ?
C9 C10 S1 109.6(2) . . ?
C11 C10 S1 129.3(3) . . ?
C12 C11 C10 136.4(3) . . ?
C12 C11 H11 111.8 . . ?
C10 C11 H11 111.8 . . ?
C11 C12 C13 135.7(3) . . ?
C11 C12 H12 112.1 . . ?
C13 C12 H12 112.1 . . ?
C14 C13 C12 122.2(3) . . ?
C14 C13 S2 109.6(3) . . ?
C12 C13 S2 128.2(3) . . ?
C15 C14 C13 114.7(3) . . ?
C15 C14 H14 122.7 . . ?
C13 C14 H14 122.7 . . ?
C14 C15 C16 113.2(3) . . ?
C14 C15 H15 123.4 . . ?
C16 C15 H15 123.4 . . ?
C15 C16 C17 125.5(3) . . ?
C15 C16 S2 109.5(3) . . ?
C17 C16 S2 125.0(3) . . ?
C16 C17 C7 126.5(3) . 2_655 ?
C16 C17 C18 116.8(3) . . ?
C7 C17 C18 116.7(3) 2_655 . ?
C23 C18 C19 118.4(3) . . ?
C23 C18 C17 122.3(3) . . ?
C19 C18 C17 119.3(3) . . ?
C20 C19 C18 120.4(3) . . ?
C20 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C19 C20 C21 120.2(3) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 H20 119.9 . . ?
C22 C21 C20 119.8(3) . . ?
C22 C21 H21 120.1 . . ?
C20 C21 H21 120.1 . . ?
C21 C22 C23 120.2(3) . . ?
C21 C22 H22 119.9 . . ?
C23 C22 H22 119.9 . . ?
C22 C23 C18 120.9(3) . . ?
C22 C23 H23 119.5 . . ?
C18 C23 H23 119.5 . . ?

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
F2 C1 C2 F1 0.1(5) . . . . ?
C3 C1 C2 F1 180.0(3) 2_575 . . . ?
F2 C1 C2 C3 -179.5(3) . . . . ?
C3 C1 C2 C3 0.4(6) 2_575 . . . ?
F1 C2 C3 C1 -179.9(3) . . . 2_575 ?
C1 C2 C3 C1 -0.4(5) . . . 2_575 ?
F1 C2 C3 C5 -0.5(5) . . . . ?
C1 C2 C3 C5 179.0(3) . . . . ?
C1 C3 C5 C4 -2.2(5) 2_575 . . . ?
C2 C3 C5 C4 178.5(3) . . . . ?
C1 C3 C5 C6 178.3(3) 2_575 . . . ?
C2 C3 C5 C6 -1.0(5) . . . . ?
N2 C4 C5 C3 -170(4) . . . . ?
N2 C4 C5 C6 10(5) . . . . ?
C3 C5 C6 N1 -180(100) . . . . ?
C4 C5 C6 N1 1(5) . . . . ?
C10 S1 C7 C8 -1.0(3) . . . . ?
C10 S1 C7 C17 176.8(3) . . . 2_655 ?
C17 C7 C8 C9 -177.5(3) 2_655 . . . ?
S1 C7 C8 C9 0.3(4) . . . . ?
C7 C8 C9 C10 0.8(4) . . . . ?
C8 C9 C10 C11 175.1(3) . . . . ?
C8 C9 C10 S1 -1.5(4) . . . . ?
C7 S1 C10 C9 1.4(3) . . . . ?
C7 S1 C10 C11 -174.8(3) . . . . ?
C9 C10 C11 C12 -178.4(4) . . . . ?
S1 C10 C11 C12 -2.5(6) . . . . ?
C10 C11 C12 C13 -0.8(8) . . . . ?
C11 C12 C13 C14 -179.6(4) . . . . ?
C11 C12 C13 S2 -0.4(6) . . . . ?
C16 S2 C13 C14 -0.4(3) . . . . ?
C16 S2 C13 C12 -179.7(3) . . . . ?
C12 C13 C14 C15 179.6(3) . . . . ?
S2 C13 C14 C15 0.3(4) . . . . ?
C13 C14 C15 C16 0.1(5) . . . . ?
C14 C15 C16 C17 177.9(3) . . . . ?
C14 C15 C16 S2 -0.4(4) . . . . ?
C13 S2 C16 C15 0.5(3) . . . . ?
C13 S2 C16 C17 -177.8(3) . . . . ?
C15 C16 C17 C7 -171.7(3) . . . 2_655 ?
S2 C16 C17 C7 6.4(5) . . . 2_655 ?
C15 C16 C17 C18 10.8(5) . . . . ?
S2 C16 C17 C18 -171.2(2) . . . . ?
C16 C17 C18 C23 -122.2(4) . . . . ?
C7 C17 C18 C23 60.0(4) 2_655 . . . ?
C16 C17 C18 C19 59.0(4) . . . . ?
C7 C17 C18 C19 -118.8(4) 2_655 . . . ?
C23 C18 C19 C20 -1.4(5) . . . . ?
C17 C18 C19 C20 177.3(3) . . . . ?
C18 C19 C20 C21 0.2(5) . . . . ?
C19 C20 C21 C22 0.6(5) . . . . ?
C20 C21 C22 C23 -0.2(5) . . . . ?
C21 C22 C23 C18 -1.0(5) . . . . ?
C19 C18 C23 C22 1.8(5) . . . . ?
C17 C18 C23 C22 -176.9(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.952
_refine_diff_density_min         -0.678
_refine_diff_density_rms         0.126
