# Supplementary Material (ESI) for Journal of Materials Chemistry
# This journal is (C) The Royal Society of Chemistry 2008

data_global
_journal_name_full               J.Mater.Chem.
_journal_coden_cambridge         1145

_publ_section_title              
;A New Type of Light-Emitting Naphtho[2,3-c][1,2,5]thiadiazole Derivatives:
Synthesis, Photophysical Characterization and Transporting Property
;
_publ_contact_author_name        'Prof. Yong Qiu'
_publ_contact_author_email       QIUY@MAIL.TSINGHUA.EDU.CN
loop_
_publ_author_name
'Yong Qiu'
'Guifang Dong'
'Lian Duan'
'Juan Qiao'
'Liduo Wang'
;
Ruji Wang
;
'Peng Wei'
'Deqiang Zhang'

# Attachment 'Single-crystal of 1.CIF'

data_weip-2
_database_code_depnum_ccdc_archive 'CCDC 661950'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C50 H34 N2 S'
_chemical_formula_sum            'C50 H34 N2 S'
_chemical_formula_weight         694.85

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
_symmetry_space_group_name_Hall  '-P 1'

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

_cell_length_a                   6.0191(11)
_cell_length_b                   9.059(2)
_cell_length_c                   17.191(6)
_cell_angle_alpha                100.69(2)
_cell_angle_beta                 95.305(19)
_cell_angle_gamma                91.741(15)
_cell_volume                     916.1(4)
_cell_formula_units_Z            1
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    43
_cell_measurement_theta_min      4.43
_cell_measurement_theta_max      12.39

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             364
_exptl_absorpt_coefficient_mu    0.127
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      295(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  'Bruker P4'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         3
_diffrn_standards_interval_count 97
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            4199
_diffrn_reflns_av_R_equivalents  0.0554
_diffrn_reflns_av_sigmaI/netI    0.1218
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.29
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3211
_reflns_number_gt                1256
_reflns_threshold_expression     I>2\s(I)

_computing_data_collection       'XSCANS (Bruker, 1997)'
_computing_cell_refinement       'XSCANS (Bruker, 1997)'
_computing_data_reduction        'XSCANS (Bruker, 1997)'
_computing_structure_solution    'SHELXTL (Bruker, 1997)'
_computing_structure_refinement  'SHELXTL (Bruker, 1997)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  'SHELXTL (Bruker, 1997)'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
It was tried for compound 1 as an ordered structure to refine with space
group P1. The thermal parameters of several atoms were not reasonable, too
large or too small, even the anisotropic thermal parameters of a carbon atom
of the NTD group were non-positive definite. So, the disordered structure
with space group P-1 was used here.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0010P)^2^+2.0000P] where P=(Fo^2^+2Fc^2^)/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     SHELXL
_refine_ls_extinction_coef       0.0311(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         3211
_refine_ls_number_parameters     309
_refine_ls_number_restraints     40
_refine_ls_R_factor_all          0.2145
_refine_ls_R_factor_gt           0.1114
_refine_ls_wR_factor_ref         0.2355
_refine_ls_wR_factor_gt          0.2111
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_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 1.0047(5) 0.6501(3) 0.60819(17) 0.0931(10) Uani 0.50 1 d PD A 1
N1 N 0.8362(9) 0.5124(6) 0.6211(3) 0.078(3) Uani 0.50 1 d PD A 1
N2 N 0.8661(9) 0.6956(7) 0.5293(3) 0.113(3) Uani 0.50 1 d PD A 1
C2' C 0.6725(6) 0.6094(4) 0.5128(2) 0.0733(14) Uani 0.50 1 d P A 1
C3' C 0.6646(6) 0.4976(4) 0.5617(2) 0.0702(13) Uani 0.50 1 d P . 1
C1 C 0.5115(7) 0.6160(4) 0.4514(2) 0.0672(13) Uani 1 1 d . . .
C2 C 0.6725(6) 0.6094(4) 0.5128(2) 0.0733(14) Uani 0.50 1 d PD A 2
C3 C 0.6646(6) 0.4976(4) 0.5617(2) 0.0702(13) Uani 0.50 1 d PD . 2
C4 C 0.8493(10) 0.5002(8) 0.6183(5) 0.094(4) Uani 0.50 1 d PD A 2
H4A H 0.8741 0.4082 0.6372 0.112 Uiso 0.50 1 d PR A 2
C5 C 1.0111(15) 0.6163(7) 0.6399(4) 0.111(5) Uani 0.50 1 d PD A 2
H5A H 1.0915 0.6305 0.6918 0.133 Uiso 0.50 1 d PR A 2
C6 C 1.0273(13) 0.7176(9) 0.5888(4) 0.123(5) Uani 0.50 1 d PD A 2
H6A H 1.1487 0.7920 0.6005 0.147 Uiso 0.50 1 d PR A 2
C7 C 0.8512(9) 0.7176(7) 0.5308(5) 0.064(3) Uani 0.50 1 d PD A 2
H7A H 0.8733 0.7842 0.4945 0.077 Uiso 0.50 1 d PR A 2
C8 C 0.5119(6) 0.7320(4) 0.4024(2) 0.0760(14) Uani 0.50 1 d PD A 3
C9 C 0.3404(11) 0.8316(6) 0.4016(4) 0.075(3) Uani 0.50 1 d PD A 3
H9A H 0.2104 0.8162 0.4281 0.090 Uiso 0.50 1 d PR A 3
C10 C 0.3613(10) 0.9510(6) 0.3629(4) 0.069(3) Uani 0.50 1 d PD A 3
H10A H 0.2514 1.0258 0.3685 0.083 Uiso 0.50 1 d PR A 3
C11 C 0.5330(6) 0.9682(4) 0.3155(2) 0.0704(13) Uani 0.50 1 d PD A 3
C12 C 0.6947(12) 0.8630(6) 0.3145(5) 0.117(4) Uani 0.50 1 d PD A 3
H12A H 0.8143 0.8702 0.2819 0.140 Uiso 0.50 1 d PR A 3
C13 C 0.6835(11) 0.7451(7) 0.3551(4) 0.082(3) Uani 0.50 1 d PD A 3
H13A H 0.7887 0.6671 0.3495 0.098 Uiso 0.50 1 d PR A 3
C8' C 0.5119(6) 0.7320(4) 0.4024(2) 0.0760(14) Uani 0.50 1 d PD A 4
C9' C 0.4609(17) 0.8789(5) 0.4349(4) 0.101(4) Uani 0.50 1 d PD A 4
H9'A H 0.4039 0.8965 0.4860 0.121 Uiso 0.50 1 d PR A 4
C10' C 0.4784(18) 0.9961(8) 0.3941(3) 0.113(4) Uani 0.50 1 d PD A 4
H10B H 0.4641 1.0986 0.4195 0.136 Uiso 0.50 1 d PR A 4
C11' C 0.5330(6) 0.9682(4) 0.3155(2) 0.0704(13) Uani 0.50 1 d PD A 4
C12' C 0.6091(14) 0.8273(5) 0.2884(4) 0.071(3) Uani 0.50 1 d PD A 4
H12B H 0.6711 0.8085 0.2382 0.085 Uiso 0.50 1 d PR A 4
C13' C 0.5945(13) 0.7096(6) 0.3287(3) 0.061(3) Uani 0.50 1 d PD A 4
H13B H 0.6429 0.6128 0.3053 0.073 Uiso 0.50 1 d PR A 4
C14 C 0.5336(7) 1.0995(4) 0.2755(2) 0.0642(12) Uani 1 1 d . . .
H14A H 0.4683 1.1834 0.3022 0.077 Uiso 1 1 calc R A 3
C15 C 0.6117(6) 1.1174(4) 0.2078(2) 0.0608(12) Uani 1 1 d . A .
C16 C 0.5689(7) 1.2636(4) 0.1780(2) 0.0604(12) Uani 1 1 d . . .
C17 C 0.3787(8) 1.3389(5) 0.1909(3) 0.0836(15) Uani 1 1 d . A .
H17A H 0.2696 1.2987 0.2169 0.100 Uiso 1 1 calc R . .
C18 C 0.3443(8) 1.4758(5) 0.1656(3) 0.0960(16) Uani 1 1 d . . .
H18A H 0.2207 1.5306 0.1788 0.115 Uiso 1 1 calc R A .
C19 C 0.4936(9) 1.5263(5) 0.1217(3) 0.1014(18) Uani 1 1 d . A .
H19A H 0.4672 1.6129 0.1012 0.122 Uiso 1 1 calc R . .
C20 C 0.6831(8) 1.4515(5) 0.1072(3) 0.0924(16) Uani 1 1 d . . .
H20A H 0.7869 1.4904 0.0785 0.111 Uiso 1 1 calc R A .
C21 C 0.7246(8) 1.3199(4) 0.1338(3) 0.0799(14) Uani 1 1 d . A .
H21A H 0.8534 1.2693 0.1226 0.096 Uiso 1 1 calc R . .
C22 C 0.7473(7) 1.0118(4) 0.1585(2) 0.0616(12) Uani 1 1 d . . .
C23 C 0.6614(7) 0.9385(4) 0.0846(3) 0.0776(14) Uani 1 1 d . A .
H23A H 0.5166 0.9569 0.0661 0.093 Uiso 1 1 calc R . .
C24 C 0.7819(8) 0.8378(5) 0.0361(3) 0.0885(17) Uani 1 1 d . . .
H24A H 0.7201 0.7905 -0.0143 0.106 Uiso 1 1 calc R A .
C25 C 0.9945(9) 0.8095(5) 0.0641(3) 0.0968(17) Uani 1 1 d . A .
H25A H 1.0775 0.7416 0.0327 0.116 Uiso 1 1 calc R . .
C26 C 1.0861(8) 0.8819(6) 0.1392(3) 0.104(2) Uani 1 1 d . . .
H26A H 1.2299 0.8618 0.1578 0.125 Uiso 1 1 calc R A .
C27 C 0.9654(7) 0.9833(5) 0.1863(3) 0.0727(14) Uani 1 1 d . A .
H27A H 1.0282 1.0325 0.2361 0.087 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0760(17) 0.1013(19) 0.0965(19) 0.0052(16) 0.0068(15) 0.0043(15)
N1 0.134(6) 0.068(4) 0.039(3) 0.012(3) 0.038(4) 0.034(4)
N2 0.164(6) 0.097(5) 0.113(5) 0.060(4) 0.094(5) 0.071(5)
C2' 0.084(3) 0.059(2) 0.084(3) 0.026(2) 0.021(2) 0.010(2)
C3' 0.091(3) 0.071(2) 0.056(2) 0.0282(19) 0.009(2) 0.019(2)
C1 0.080(3) 0.059(2) 0.071(2) 0.0260(19) 0.022(2) 0.012(2)
C2 0.084(3) 0.059(2) 0.084(3) 0.026(2) 0.021(2) 0.010(2)
C3 0.091(3) 0.071(2) 0.056(2) 0.0282(19) 0.009(2) 0.019(2)
C4 0.051(6) 0.066(6) 0.163(11) 0.035(7) -0.026(7) 0.011(5)
C5 0.144(10) 0.115(9) 0.066(7) -0.004(6) 0.026(7) -0.043(8)
C6 0.131(10) 0.134(10) 0.113(9) 0.026(8) 0.050(8) 0.028(8)
C7 0.045(5) 0.035(4) 0.108(8) 0.013(5) -0.009(5) -0.007(4)
C8 0.090(3) 0.066(2) 0.084(3) 0.032(2) 0.025(2) 0.034(2)
C9 0.072(5) 0.084(5) 0.084(5) 0.042(4) 0.031(5) 0.004(5)
C10 0.086(5) 0.048(4) 0.086(5) 0.028(4) 0.040(4) 0.032(4)
C11 0.091(3) 0.058(2) 0.072(2) 0.0252(19) 0.020(2) 0.024(2)
C12 0.127(7) 0.100(6) 0.161(8) 0.080(5) 0.091(6) 0.039(6)
C13 0.099(7) 0.057(5) 0.094(6) 0.029(5) 0.001(6) 0.006(5)
C8' 0.090(3) 0.066(2) 0.084(3) 0.032(2) 0.025(2) 0.034(2)
C9' 0.157(9) 0.062(5) 0.100(6) 0.032(5) 0.059(6) 0.023(6)
C10' 0.183(11) 0.075(6) 0.089(7) 0.016(6) 0.046(8) 0.026(7)
C11' 0.091(3) 0.058(2) 0.072(2) 0.0252(19) 0.020(2) 0.024(2)
C12' 0.109(7) 0.066(5) 0.049(4) 0.030(4) 0.024(5) 0.020(5)
C13' 0.090(6) 0.026(4) 0.064(5) 0.008(4) 0.005(5) -0.005(4)
C14 0.069(3) 0.055(2) 0.073(3) 0.0217(19) 0.010(2) 0.011(2)
C15 0.059(2) 0.056(2) 0.071(2) 0.0215(19) 0.006(2) 0.003(2)
C16 0.065(3) 0.046(2) 0.073(2) 0.0180(18) 0.006(2) 0.0128(19)
C17 0.087(3) 0.065(2) 0.108(3) 0.034(2) 0.022(3) 0.007(2)
C18 0.106(3) 0.078(3) 0.122(4) 0.041(3) 0.052(3) 0.037(3)
C19 0.126(4) 0.078(3) 0.116(4) 0.046(3) 0.026(3) 0.025(3)
C20 0.097(3) 0.083(3) 0.115(3) 0.051(2) 0.039(3) 0.013(3)
C21 0.082(3) 0.068(2) 0.104(3) 0.044(2) 0.026(3) 0.012(2)
C22 0.066(3) 0.058(2) 0.068(2) 0.0245(19) 0.016(2) 0.006(2)
C23 0.073(3) 0.081(3) 0.091(3) 0.042(2) 0.018(2) 0.015(2)
C24 0.090(3) 0.092(3) 0.086(3) 0.023(3) 0.009(3) 0.008(3)
C25 0.114(4) 0.078(3) 0.106(4) 0.019(3) 0.044(3) 0.015(3)
C26 0.080(3) 0.123(4) 0.115(4) 0.029(3) 0.025(3) 0.019(3)
C27 0.067(3) 0.074(3) 0.076(3) 0.014(2) 0.005(2) -0.001(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 N1 1.643(6) . ?
S1 N2 1.650(6) . ?
N1 C3 1.369(6) . ?
N2 C2 1.360(6) . ?
C2 C1 1.377(5) . ?
C2 C7 1.405(6) . ?
C2 C3 1.432(5) . ?
C3 C4 1.406(6) . ?
C3 C1 1.428(5) 2_666 ?
C1 C3 1.428(5) 2_666 ?
C1 C8 1.464(5) . ?
C4 C5 1.385(7) . ?
C4 H4A 0.9600 . ?
C5 C6 1.389(8) . ?
C5 H5A 0.9601 . ?
C6 C7 1.386(7) . ?
C6 H6A 0.9600 . ?
C7 H7A 0.9599 . ?
C8 C13' 1.386(6) . ?
C8 C13 1.388(7) . ?
C8 C9 1.392(6) . ?
C8 C9' 1.400(6) . ?
C9 C10 1.379(7) . ?
C9 H9A 0.9600 . ?
C10 C11 1.397(6) . ?
C10 H10A 0.9600 . ?
C11 C12 1.382(6) . ?
C11 C12' 1.382(6) . ?
C11 C10' 1.399(6) . ?
C11 C14 1.480(5) . ?
C12 C13 1.383(7) . ?
C12 H12A 0.9601 . ?
C13 H13A 0.9600 . ?
C9' C10' 1.383(7) . ?
C9' H9'A 0.9602 . ?
C10' H10B 0.9600 . ?
C12' C13' 1.381(7) . ?
C12' H12B 0.9600 . ?
C13' H13B 0.9600 . ?
C14 C15 1.331(6) . ?
C14 H14A 0.9300 . ?
C15 C22 1.474(5) . ?
C15 C16 1.526(5) . ?
C16 C17 1.365(6) . ?
C16 C21 1.401(6) . ?
C17 C18 1.403(6) . ?
C17 H17A 0.9300 . ?
C18 C19 1.346(7) . ?
C18 H18A 0.9300 . ?
C19 C20 1.364(7) . ?
C19 H19A 0.9300 . ?
C20 C21 1.375(6) . ?
C20 H20A 0.9300 . ?
C21 H21A 0.9300 . ?
C22 C23 1.366(5) . ?
C22 C27 1.403(6) . ?
C23 C24 1.387(6) . ?
C23 H23A 0.9300 . ?
C24 C25 1.374(7) . ?
C24 H24A 0.9300 . ?
C25 C26 1.391(7) . ?
C25 H25A 0.9300 . ?
C26 C27 1.378(6) . ?
C26 H26A 0.9300 . ?
C27 H27A 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
N1 S1 N2 99.1(3) . . ?
C3 N1 S1 106.5(4) . . ?
C2 N2 S1 107.8(4) . . ?
N2 C2 C1 124.9(4) . . ?
C1 C2 C7 119.8(4) . . ?
N2 C2 C3 112.0(4) . . ?
C1 C2 C3 122.8(3) . . ?
C7 C2 C3 117.4(4) . . ?
N1 C3 C1 124.4(4) . 2_666 ?
C4 C3 C1 122.6(4) . 2_666 ?
N1 C3 C2 114.1(4) . . ?
C4 C3 C2 115.7(4) . . ?
C1 C3 C2 121.5(3) 2_666 . ?
C2 C1 C3 115.7(3) . 2_666 ?
C2 C1 C8 123.8(4) . . ?
C3 C1 C8 120.5(4) 2_666 . ?
C5 C4 C3 124.9(7) . . ?
C5 C4 H4A 118.4 . . ?
C3 C4 H4A 116.1 . . ?
C4 C5 C6 117.5(7) . . ?
C4 C5 H5A 118.7 . . ?
C6 C5 H5A 123.3 . . ?
C7 C6 C5 117.6(7) . . ?
C7 C6 H6A 123.9 . . ?
C5 C6 H6A 117.9 . . ?
C6 C7 C2 124.6(7) . . ?
C6 C7 H7A 115.0 . . ?
C2 C7 H7A 119.0 . . ?
C13 C8 C9 118.2(5) . . ?
C13' C8 C9' 117.0(5) . . ?
C13' C8 C1 122.6(4) . . ?
C13 C8 C1 120.7(4) . . ?
C9 C8 C1 121.1(4) . . ?
C9' C8 C1 119.6(4) . . ?
C10 C9 C8 119.2(6) . . ?
C10 C9 H9A 121.3 . . ?
C8 C9 H9A 119.5 . . ?
C9 C10 C11 123.5(5) . . ?
C9 C10 H10A 118.3 . . ?
C11 C10 H10A 118.2 . . ?
C12 C11 C10 115.4(5) . . ?
C12' C11 C10' 116.1(5) . . ?
C12 C11 C14 126.3(4) . . ?
C12' C11 C14 127.4(4) . . ?
C10 C11 C14 118.2(4) . . ?
C10' C11 C14 115.9(4) . . ?
C11 C12 C13 122.5(6) . . ?
C11 C12 H12A 117.8 . . ?
C13 C12 H12A 119.6 . . ?
C12 C13 C8 120.6(6) . . ?
C12 C13 H13A 121.5 . . ?
C8 C13 H13A 117.8 . . ?
C10' C9' C8 122.2(6) . . ?
C10' C9' H9'A 119.6 . . ?
C8 C9' H9'A 118.1 . . ?
C9' C10' C11 120.1(6) . . ?
C9' C10' H10B 121.6 . . ?
C11 C10' H10B 118.1 . . ?
C13' C12' C11 123.3(6) . . ?
C13' C12' H12B 117.7 . . ?
C11 C12' H12B 118.9 . . ?
C12' C13' C8 120.0(5) . . ?
C12' C13' H13B 119.4 . . ?
C8 C13' H13B 120.6 . . ?
C15 C14 C11 130.8(4) . . ?
C15 C14 H14A 114.6 . . ?
C11 C14 H14A 114.6 . . ?
C14 C15 C22 126.5(4) . . ?
C14 C15 C16 118.5(3) . . ?
C22 C15 C16 115.0(3) . . ?
C17 C16 C21 118.7(4) . . ?
C17 C16 C15 121.8(4) . . ?
C21 C16 C15 119.4(4) . . ?
C16 C17 C18 121.4(4) . . ?
C16 C17 H17A 119.3 . . ?
C18 C17 H17A 119.3 . . ?
C19 C18 C17 118.8(5) . . ?
C19 C18 H18A 120.6 . . ?
C17 C18 H18A 120.6 . . ?
C18 C19 C20 120.5(5) . . ?
C18 C19 H19A 119.7 . . ?
C20 C19 H19A 119.7 . . ?
C19 C20 C21 121.6(5) . . ?
C19 C20 H20A 119.2 . . ?
C21 C20 H20A 119.2 . . ?
C20 C21 C16 118.7(4) . . ?
C20 C21 H21A 120.6 . . ?
C16 C21 H21A 120.6 . . ?
C23 C22 C27 118.6(4) . . ?
C23 C22 C15 120.3(4) . . ?
C27 C22 C15 121.1(3) . . ?
C22 C23 C24 122.5(4) . . ?
C22 C23 H23A 118.7 . . ?
C24 C23 H23A 118.7 . . ?
C25 C24 C23 118.5(4) . . ?
C25 C24 H24A 120.7 . . ?
C23 C24 H24A 120.7 . . ?
C24 C25 C26 120.3(5) . . ?
C24 C25 H25A 119.9 . . ?
C26 C25 H25A 119.9 . . ?
C27 C26 C25 120.5(5) . . ?
C27 C26 H26A 119.7 . . ?
C25 C26 H26A 119.7 . . ?
C26 C27 C22 119.6(4) . . ?
C26 C27 H27A 120.2 . . ?
C22 C27 H27A 120.2 . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.057

# Attachment 'Single-crystal of 3.CIF'

data_try
_database_code_depnum_ccdc_archive 'CCDC 661951'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C34 H22 N2 S'
_chemical_formula_sum            'C34 H22 N2 S'
_chemical_formula_weight         490.60

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           Monoclinic
_symmetry_space_group_name_H-M   C2/c
_symmetry_space_group_name_Hall  '-C 2yc'

loop_
_symmetry_equiv_pos_as_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                   9.3698(10)
_cell_length_b                   28.450(3)
_cell_length_c                   9.4857(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.178(3)
_cell_angle_gamma                90.00
_cell_volume                     2415.8(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    1212
_cell_measurement_theta_min      2.3
_cell_measurement_theta_max      23.9

_exptl_crystal_description       sheet
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1024
_exptl_absorpt_coefficient_mu    0.162
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      295(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  'Bruker SMART APEX-CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean 15X15microns
_diffrn_standards_number         none
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            6151
_diffrn_reflns_av_R_equivalents  0.0371
_diffrn_reflns_av_sigmaI/netI    0.0437
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.39
_diffrn_reflns_theta_max         26.37
_reflns_number_total             2463
_reflns_number_gt                1585
_reflns_threshold_expression     I>2\s(I)

_computing_data_collection       'SMART (Bruker, 1997)'
_computing_cell_refinement       'SAINT (Bruker, 1997)'
_computing_data_reduction        'SAINT (Bruker, 1997)'
_computing_structure_solution    'SHELXTL (Bruker, 1997)'
_computing_structure_refinement  'SHELXTL (Bruker, 1997)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  'SHELXTL (Bruker, 1997)'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
It was tried for compound 3 as an ordered structure to refine with space
group Cc. The thermal parameters of several atoms were not reasonable, too
large or too small, even the anisotropic thermal parameters of 2 carbon
atoms of the NTD group were non-positive definite and gave unreasonable
C-C bonds. So, the disordered structure with space group C2/c was used here.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0010P)^2^+7.5000P] where P=(Fo^2^+2Fc^2^)/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         2463
_refine_ls_number_parameters     192
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1079
_refine_ls_R_factor_gt           0.0727
_refine_ls_wR_factor_ref         0.1501
_refine_ls_wR_factor_gt          0.1376
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.048
_refine_ls_shift/su_mean         0.002

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 0.21148(13) 0.51529(5) 0.89514(15) 0.0686(4) Uani 0.50 1 d PD A 1
N1 N 0.2912(4) 0.56086(12) 0.8409(4) 0.0574(7) Uani 0.50 1 d PD A 1
N2 N 0.3064(3) 0.47088(12) 0.8565(4) 0.0514(7) Uani 0.50 1 d PD A 1
C1 C 0.5000 0.56580(10) 0.7500 0.0492(8) Uani 1 2 d S . .
C2 C 0.3984(2) 0.48902(7) 0.8030(2) 0.0489(6) Uani 1 1 d . . .
C3 C 0.3962(2) 0.53998(7) 0.7992(2) 0.0487(6) Uani 1 1 d . A .
C5 C 0.2772(6) 0.56078(19) 0.8525(6) 0.0574(7) Uani 0.50 1 d P A 2
H5A H 0.2752 0.5935 0.8500 0.069 Uiso 0.50 1 d PR A 2
C6 C 0.1730(5) 0.53937(17) 0.8987(5) 0.0626(14) Uani 0.50 1 d P A 2
H6A H 0.1029 0.5556 0.9317 0.075 Uiso 0.50 1 d PR A 2
C7 C 0.1865(5) 0.48861(16) 0.9175(5) 0.0631(14) Uani 0.50 1 d P A 2
H7A H 0.1183 0.4722 0.9529 0.076 Uiso 0.50 1 d PR A 2
C8 C 0.2820(5) 0.46631(18) 0.8710(6) 0.0514(7) Uani 0.50 1 d P A 2
H8A H 0.2840 0.4336 0.8735 0.062 Uiso 0.50 1 d PR A 2
C4 C 0.5000 0.46287(10) 0.7500 0.0483(8) Uani 1 2 d S . .
C9 C 0.5000 0.61817(10) 0.7500 0.0470(8) Uani 1 2 d S . .
C10 C 0.4685(2) 0.64351(7) 0.6197(2) 0.0548(6) Uani 1 1 d . . .
H10A H 0.4470 0.6275 0.5304 0.066 Uiso 1 1 calc R . .
C11 C 0.4681(2) 0.69203(7) 0.6192(2) 0.0503(6) Uani 1 1 d . . .
H11A H 0.4460 0.7079 0.5296 0.060 Uiso 1 1 calc R . .
C12 C 0.5000 0.71783(10) 0.7500 0.0443(8) Uani 1 2 d S . .
C13 C 0.5000 0.77025(10) 0.7500 0.0440(8) Uani 1 2 d S . .
C14 C 0.4321(2) 0.79569(8) 0.6226(3) 0.0571(7) Uani 1 1 d . . .
H14A H 0.3857 0.7798 0.5354 0.069 Uiso 1 1 calc R . .
C15 C 0.4326(3) 0.84438(8) 0.6239(3) 0.0663(8) Uani 1 1 d . . .
H15A H 0.3864 0.8607 0.5376 0.080 Uiso 1 1 calc R . .
C16 C 0.5000 0.86879(11) 0.7500 0.0644(10) Uani 1 2 d S . .
H16A H 0.5000 0.9025 0.7500 0.077 Uiso 1 2 d SR . .
C17 C 0.5000 0.41087(10) 0.7500 0.0466(8) Uani 1 2 d S . .
C18 C 0.6315(2) 0.38572(7) 0.8055(2) 0.0499(6) Uani 1 1 d . A .
H18A H 0.7212 0.4017 0.8436 0.060 Uiso 1 1 calc R . .
C19 C 0.6305(2) 0.33697(7) 0.8049(2) 0.0491(6) Uani 1 1 d . . .
H19A H 0.7203 0.3210 0.8426 0.059 Uiso 1 1 calc R A .
C20 C 0.5000 0.31114(10) 0.7500 0.0446(8) Uani 1 2 d S . .
C21 C 0.5000 0.25869(10) 0.7500 0.0456(8) Uani 1 2 d S . .
C22 C 0.6309(3) 0.23363(8) 0.7970(3) 0.0688(8) Uani 1 1 d . A .
H22A H 0.7212 0.2497 0.8293 0.083 Uiso 1 1 calc R . .
C23 C 0.6310(3) 0.18492(8) 0.7970(3) 0.0746(9) Uani 1 1 d . . .
H23A H 0.7211 0.1688 0.8294 0.090 Uiso 1 1 calc R A .
C24 C 0.5000 0.16037(12) 0.7500 0.0662(11) Uani 1 2 d S . .
H24A H 0.5000 0.1266 0.7500 0.079 Uiso 1 2 d SR . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0634(6) 0.0671(8) 0.0906(7) -0.0121(7) 0.0465(5) -0.0029(6)
N1 0.0651(12) 0.0459(11) 0.0672(13) -0.0057(10) 0.0288(10) -0.0055(10)
N2 0.0490(12) 0.0469(12) 0.0708(13) -0.0048(10) 0.0368(10) -0.0077(10)
C1 0.0552(16) 0.0404(15) 0.0491(16) 0.000 0.0107(14) 0.000
C2 0.0520(11) 0.0452(11) 0.0492(11) 0.0002(10) 0.0144(9) -0.0021(9)
C3 0.0520(11) 0.0427(11) 0.0510(11) -0.0041(9) 0.0147(9) 0.0023(9)
C5 0.0651(12) 0.0459(11) 0.0672(13) -0.0057(10) 0.0288(10) -0.0055(10)
C6 0.058(2) 0.055(3) 0.083(3) -0.012(2) 0.034(2) 0.014(2)
C7 0.070(3) 0.046(2) 0.080(3) 0.004(2) 0.033(2) -0.020(2)
C8 0.0490(12) 0.0469(12) 0.0708(13) -0.0048(10) 0.0368(10) -0.0077(10)
C4 0.0516(15) 0.0423(16) 0.0509(16) 0.000 0.0150(13) 0.000
C9 0.0474(15) 0.0384(15) 0.0542(17) 0.000 0.0133(13) 0.000
C10 0.0690(13) 0.0493(12) 0.0459(11) -0.0045(10) 0.0168(10) 0.0049(11)
C11 0.0653(12) 0.0435(11) 0.0430(11) 0.0028(9) 0.0172(9) 0.0056(10)
C12 0.0424(13) 0.0460(16) 0.0482(15) 0.000 0.0189(12) 0.000
C13 0.0457(13) 0.0405(15) 0.0518(15) 0.000 0.0238(12) 0.000
C14 0.0636(12) 0.0480(12) 0.0594(13) -0.0014(10) 0.0175(11) 0.0057(10)
C15 0.0701(14) 0.0471(13) 0.0838(16) 0.0096(12) 0.0260(12) 0.0060(11)
C16 0.0592(17) 0.0416(17) 0.099(2) 0.000 0.0331(17) 0.000
C17 0.0543(15) 0.0394(15) 0.0510(16) 0.000 0.0229(12) 0.000
C18 0.0458(10) 0.0487(12) 0.0565(12) -0.0079(10) 0.0173(9) -0.0070(9)
C19 0.0471(10) 0.0454(11) 0.0557(12) -0.0018(10) 0.0163(9) 0.0038(9)
C20 0.0498(14) 0.0455(16) 0.0437(14) 0.000 0.0219(12) 0.000
C21 0.0508(14) 0.0453(16) 0.0448(15) 0.000 0.0205(12) 0.000
C22 0.0498(12) 0.0500(13) 0.1021(19) 0.0048(13) 0.0152(13) -0.0016(11)
C23 0.0577(13) 0.0489(13) 0.110(2) 0.0040(14) 0.0141(14) 0.0058(11)
C24 0.070(2) 0.0460(18) 0.084(2) 0.000 0.0246(18) 0.000

_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 N2 1.648(4) . ?
S1 N1 1.652(4) . ?
N1 C3 1.307(5) . ?
N2 C2 1.235(4) . ?
C1 C3 1.404(3) 2_656 ?
C1 C3 1.404(3) . ?
C1 C9 1.490(4) . ?
C2 C4 1.413(3) . ?
C2 C3 1.450(3) . ?
C2 C8 1.561(6) . ?
C3 C5 1.478(6) . ?
C5 C6 1.330(8) . ?
C5 H5A 0.9301 . ?
C6 C7 1.456(6) . ?
C6 H6A 0.9299 . ?
C7 C8 1.278(7) . ?
C7 H7A 0.9299 . ?
C8 H8A 0.9301 . ?
C4 C2 1.413(3) 2_656 ?
C4 C17 1.479(4) . ?
C9 C10 1.386(3) . ?
C9 C10 1.386(3) 2_656 ?
C10 C11 1.380(3) . ?
C10 H10A 0.9300 . ?
C11 C12 1.396(2) . ?
C11 H11A 0.9300 . ?
C12 C11 1.396(2) 2_656 ?
C12 C13 1.491(4) . ?
C13 C14 1.391(3) 2_656 ?
C13 C14 1.391(3) . ?
C14 C15 1.385(3) . ?
C14 H14A 0.9300 . ?
C15 C16 1.366(3) . ?
C15 H15A 0.9300 . ?
C16 C15 1.366(3) 2_656 ?
C16 H16A 0.9602 . ?
C17 C18 1.387(2) 2_656 ?
C17 C18 1.387(2) . ?
C18 C19 1.387(3) . ?
C18 H18A 0.9300 . ?
C19 C20 1.389(2) . ?
C19 H19A 0.9300 . ?
C20 C19 1.389(2) 2_656 ?
C20 C21 1.492(4) . ?
C21 C22 1.374(3) 2_656 ?
C21 C22 1.374(3) . ?
C22 C23 1.386(3) . ?
C22 H22A 0.9300 . ?
C23 C24 1.367(3) . ?
C23 H23A 0.9300 . ?
C24 C23 1.367(3) 2_656 ?
C24 H24A 0.9602 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 S1 N1 102.0(2) . . ?
C3 N1 S1 100.8(2) . . ?
C2 N2 S1 105.0(2) . . ?
C3 C1 C3 116.9(3) 2_656 . ?
C3 C1 C9 121.56(13) 2_656 . ?
C3 C1 C9 121.56(13) . . ?
N2 C2 C4 123.5(2) . . ?
N2 C2 C3 115.0(2) . . ?
C4 C2 C3 121.6(2) . . ?
C4 C2 C8 123.7(3) . . ?
C3 C2 C8 114.7(3) . . ?
N1 C3 C1 121.3(2) . . ?
N1 C3 C2 116.9(2) . . ?
C1 C3 C2 121.7(2) . . ?
C1 C3 C5 124.8(3) . . ?
C2 C3 C5 113.5(3) . . ?
C6 C5 C3 129.1(5) . . ?
C6 C5 H5A 117.1 . . ?
C3 C5 H5A 113.8 . . ?
C5 C6 C7 116.7(5) . . ?
C5 C6 H6A 122.9 . . ?
C7 C6 H6A 119.8 . . ?
C8 C7 C6 119.6(5) . . ?
C8 C7 H7A 120.1 . . ?
C6 C7 H7A 119.9 . . ?
C7 C8 C2 125.7(4) . . ?
C7 C8 H8A 119.9 . . ?
C2 C8 H8A 114.4 . . ?
C2 C4 C2 116.4(3) . 2_656 ?
C2 C4 C17 121.78(13) . . ?
C2 C4 C17 121.78(13) 2_656 . ?
C10 C9 C10 117.3(3) . 2_656 ?
C10 C9 C1 121.36(13) . . ?
C10 C9 C1 121.36(13) 2_656 . ?
C11 C10 C9 121.5(2) . . ?
C11 C10 H10A 119.2 . . ?
C9 C10 H10A 119.2 . . ?
C10 C11 C12 121.5(2) . . ?
C10 C11 H11A 119.2 . . ?
C12 C11 H11A 119.2 . . ?
C11 C12 C11 116.6(3) 2_656 . ?
C11 C12 C13 121.72(13) 2_656 . ?
C11 C12 C13 121.72(13) . . ?
C14 C13 C14 117.3(3) 2_656 . ?
C14 C13 C12 121.36(13) 2_656 . ?
C14 C13 C12 121.36(13) . . ?
C15 C14 C13 120.9(2) . . ?
C15 C14 H14A 119.6 . . ?
C13 C14 H14A 119.6 . . ?
C16 C15 C14 121.1(2) . . ?
C16 C15 H15A 119.5 . . ?
C14 C15 H15A 119.5 . . ?
C15 C16 C15 118.9(3) . 2_656 ?
C15 C16 H16A 120.6 . . ?
C15 C16 H16A 120.6 2_656 . ?
C18 C17 C18 117.9(3) 2_656 . ?
C18 C17 C4 121.05(13) 2_656 . ?
C18 C17 C4 121.05(13) . . ?
C17 C18 C19 120.67(19) . . ?
C17 C18 H18A 119.7 . . ?
C19 C18 H18A 119.7 . . ?
C18 C19 C20 122.32(19) . . ?
C18 C19 H19A 118.8 . . ?
C20 C19 H19A 118.8 . . ?
C19 C20 C19 116.1(3) . 2_656 ?
C19 C20 C21 121.93(13) . . ?
C19 C20 C21 121.93(13) 2_656 . ?
C22 C21 C22 117.5(3) 2_656 . ?
C22 C21 C20 121.26(14) 2_656 . ?
C22 C21 C20 121.26(14) . . ?
C21 C22 C23 121.3(2) . . ?
C21 C22 H22A 119.3 . . ?
C23 C22 H22A 119.3 . . ?
C24 C23 C22 120.7(2) . . ?
C24 C23 H23A 119.7 . . ?
C22 C23 H23A 119.7 . . ?
C23 C24 C23 118.6(3) . 2_656 ?
C23 C24 H24A 120.7 . . ?
C23 C24 H24A 120.7 2_656 . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.160
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.041