# Supplementary Material (ESI) for Dalton Transactions
# This journal is (c) The Royal Society of Chemistry 2011

data_global

_journal_coden_Cambridge         222
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

loop_
_publ_author_name
'Zhang, Hongyu'
'Wang, Yue'
'Li, Di'
'Zhang, Zuolun'
'Zhao, Shanshan'

_publ_contact_author_name        'Zhang, Hongyu'
_publ_contact_author_email       hongyuzhang@jlu.edu.cn

_publ_section_title              
;
Diboron-Contained Fluorophores
with Extended Ladder-Type p-Conjugated Skeleton
;

# Attachment '- 3 and 5.cif'

data_3
_database_code_depnum_ccdc_archive 'CCDC 794633'
#TrackingRef '- 3 and 5.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C52 H52 B2 N2 S2'
_chemical_formula_weight         790.72

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'
B B 0.0013 0.0007 '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   P21/c

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

_cell_length_a                   9.0889(18)
_cell_length_b                   14.676(3)
_cell_length_c                   16.295(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.18(3)
_cell_angle_gamma                90.00
_cell_volume                     2167.8(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4954
_cell_measurement_theta_min      2.99
_cell_measurement_theta_max      27.48

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.211
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             840
_exptl_absorpt_coefficient_mu    0.161
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.9700
_exptl_absorpt_correction_T_max  0.9762
_exptl_absorpt_process_details   'Higashi (1995)'

_exptl_special_details           
;
?
;

_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  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       'Omega scan'
_diffrn_detector_area_resol_mean 10.0
_diffrn_standards_number         none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        none
_diffrn_reflns_number            20384
_diffrn_reflns_av_R_equivalents  0.1747
_diffrn_reflns_av_sigmaI/netI    0.1493
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.99
_diffrn_reflns_theta_max         27.48
_reflns_number_total             4954
_reflns_number_gt                2001
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'RAPID-AUTO (Rigaku, 1998)'
_computing_cell_refinement       RAPID-AUTO
_computing_data_reduction        RAPID-AUTO
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics    SHELXP97
_computing_publication_material  SHELXL97

_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.
;

_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^)+(0.0946P)^2^+0.0000P] 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     none
_refine_ls_extinction_coef       0
_refine_ls_number_reflns         4954
_refine_ls_number_parameters     268
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2464
_refine_ls_R_factor_gt           0.1086
_refine_ls_wR_factor_ref         0.2605
_refine_ls_wR_factor_gt          0.2000
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_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
B1 B 0.3345(7) 0.0508(4) 0.1764(4) 0.0595(16) Uani 1 1 d . . .
C1 C 0.8371(6) 0.0659(4) -0.2623(3) 0.0728(16) Uani 1 1 d . . .
H1 H 0.8618 0.0210 -0.2992 0.087 Uiso 1 1 calc R . .
C2 C 0.8862(7) 0.1540(4) -0.2725(3) 0.0855(19) Uani 1 1 d . . .
H2 H 0.9453 0.1668 -0.3153 0.103 Uiso 1 1 calc R . .
C3 C 0.8499(7) 0.2230(4) -0.2210(4) 0.0810(18) Uani 1 1 d . . .
H3 H 0.8847 0.2817 -0.2288 0.097 Uiso 1 1 calc R . .
C4 C 0.7619(6) 0.2054(3) -0.1576(3) 0.0704(15) Uani 1 1 d . . .
H4 H 0.7351 0.2515 -0.1225 0.085 Uiso 1 1 calc R . .
C5 C 0.7144(6) 0.1163(3) -0.1480(3) 0.0567(13) Uani 1 1 d . . .
C6 C 0.7511(6) 0.0429(3) -0.1978(3) 0.0599(13) Uani 1 1 d . . .
C7 C 0.6236(6) 0.0830(3) -0.0848(3) 0.0564(13) Uani 1 1 d . . .
C8 C 0.4884(5) 0.0332(3) 0.0284(3) 0.0545(13) Uani 1 1 d . . .
C9 C 0.2557(6) 0.1399(3) 0.1326(3) 0.0601(14) Uani 1 1 d . . .
C10 C 0.3337(6) 0.2223(3) 0.1273(3) 0.0600(14) Uani 1 1 d . . .
C11 C 0.2694(7) 0.2975(3) 0.0866(3) 0.0658(15) Uani 1 1 d . . .
H11 H 0.3231 0.3514 0.0858 0.079 Uiso 1 1 calc R . .
C12 C 0.1302(8) 0.2953(4) 0.0478(3) 0.0747(16) Uani 1 1 d . . .
C13 C 0.0513(7) 0.2149(4) 0.0528(3) 0.0733(16) Uani 1 1 d . . .
H13 H -0.0439 0.2119 0.0279 0.088 Uiso 1 1 calc R . .
C14 C 0.1096(7) 0.1386(3) 0.0939(3) 0.0662(14) Uani 1 1 d . . .
C15 C 0.4870(7) 0.2383(3) 0.1681(3) 0.0731(17) Uani 1 1 d . . .
H15A H 0.5316 0.2893 0.1426 0.110 Uiso 1 1 calc R . .
H15B H 0.5463 0.1849 0.1622 0.110 Uiso 1 1 calc R . .
H15C H 0.4800 0.2509 0.2255 0.110 Uiso 1 1 calc R . .
C16 C 0.0627(7) 0.3785(4) 0.0053(4) 0.095(2) Uani 1 1 d . . .
H16A H 0.0221 0.4175 0.0452 0.143 Uiso 1 1 calc R . .
H16B H -0.0142 0.3600 -0.0348 0.143 Uiso 1 1 calc R . .
H16C H 0.1373 0.4110 -0.0216 0.143 Uiso 1 1 calc R . .
C17 C 0.0086(7) 0.0567(4) 0.0976(4) 0.101(2) Uani 1 1 d . . .
H17A H 0.0546 0.0047 0.0745 0.151 Uiso 1 1 calc R . .
H17B H -0.0832 0.0692 0.0667 0.151 Uiso 1 1 calc R . .
H17C H -0.0095 0.0444 0.1538 0.151 Uiso 1 1 calc R . .
C18 C 0.4400(6) 0.0693(3) 0.2599(3) 0.0594(14) Uani 1 1 d . . .
C19 C 0.3767(6) 0.1202(3) 0.3229(3) 0.0629(14) Uani 1 1 d . . .
C20 C 0.4512(7) 0.1292(3) 0.4009(3) 0.0692(16) Uani 1 1 d . . .
H20 H 0.4080 0.1634 0.4407 0.083 Uiso 1 1 calc R . .
C21 C 0.5865(7) 0.0891(3) 0.4205(3) 0.0683(15) Uani 1 1 d . . .
C22 C 0.6499(6) 0.0420(3) 0.3590(3) 0.0656(14) Uani 1 1 d . . .
H22 H 0.7435 0.0173 0.3701 0.079 Uiso 1 1 calc R . .
C23 C 0.5796(6) 0.0300(3) 0.2808(3) 0.0603(14) Uani 1 1 d . . .
C24 C 0.2308(6) 0.1702(4) 0.3116(3) 0.0820(18) Uani 1 1 d . . .
H24A H 0.1970 0.1849 0.3645 0.123 Uiso 1 1 calc R . .
H24B H 0.1594 0.1321 0.2819 0.123 Uiso 1 1 calc R . .
H24C H 0.2436 0.2253 0.2812 0.123 Uiso 1 1 calc R . .
C25 C 0.6594(7) 0.0973(4) 0.5068(3) 0.0850(18) Uani 1 1 d . . .
H25A H 0.7417 0.0562 0.5130 0.128 Uiso 1 1 calc R . .
H25B H 0.5895 0.0822 0.5460 0.128 Uiso 1 1 calc R . .
H25C H 0.6934 0.1587 0.5159 0.128 Uiso 1 1 calc R . .
C26 C 0.6623(6) -0.0266(4) 0.2217(3) 0.0806(17) Uani 1 1 d . . .
H26A H 0.7559 -0.0444 0.2478 0.121 Uiso 1 1 calc R . .
H26B H 0.6775 0.0087 0.1735 0.121 Uiso 1 1 calc R . .
H26C H 0.6058 -0.0800 0.2063 0.121 Uiso 1 1 calc R . .
N3 N 0.4140(4) 0.0045(2) 0.0945(2) 0.0555(11) Uani 1 1 d . . .
S1 S 0.56340(16) 0.13549(7) 0.00040(8) 0.0661(5) Uani 1 1 d . . .

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
B1 0.068(4) 0.051(3) 0.064(4) -0.004(3) 0.033(3) 0.003(3)
C1 0.083(4) 0.070(3) 0.070(3) 0.002(3) 0.036(3) 0.002(3)
C2 0.098(5) 0.083(4) 0.081(4) 0.014(3) 0.039(4) -0.016(4)
C3 0.091(5) 0.069(3) 0.087(4) 0.009(3) 0.032(4) -0.010(3)
C4 0.087(4) 0.057(3) 0.070(3) 0.004(3) 0.027(3) -0.006(3)
C5 0.073(4) 0.048(3) 0.051(3) 0.000(2) 0.017(3) 0.003(2)
C6 0.065(4) 0.063(3) 0.054(3) 0.004(2) 0.019(3) 0.004(3)
C7 0.073(4) 0.042(3) 0.056(3) -0.001(2) 0.018(3) 0.000(2)
C8 0.065(3) 0.043(2) 0.058(3) 0.002(2) 0.024(3) 0.003(2)
C9 0.078(4) 0.050(3) 0.056(3) -0.004(2) 0.025(3) 0.002(3)
C10 0.075(4) 0.050(3) 0.056(3) 0.002(2) 0.016(3) 0.005(3)
C11 0.088(5) 0.052(3) 0.060(3) 0.001(2) 0.025(3) 0.008(3)
C12 0.096(5) 0.064(3) 0.068(4) 0.004(3) 0.024(4) 0.020(3)
C13 0.077(4) 0.076(4) 0.067(3) -0.004(3) 0.008(3) 0.015(3)
C14 0.072(4) 0.063(3) 0.064(3) -0.006(3) 0.012(3) 0.004(3)
C15 0.093(5) 0.056(3) 0.073(4) 0.009(3) 0.021(4) -0.004(3)
C16 0.109(5) 0.082(4) 0.098(5) 0.017(3) 0.021(4) 0.030(4)
C17 0.095(5) 0.089(4) 0.117(5) 0.002(4) -0.004(4) -0.005(4)
C18 0.079(4) 0.044(2) 0.058(3) 0.002(2) 0.023(3) 0.003(3)
C19 0.076(4) 0.054(3) 0.060(3) 0.000(2) 0.019(3) -0.001(3)
C20 0.101(5) 0.051(3) 0.058(3) -0.008(2) 0.024(3) 0.000(3)
C21 0.085(5) 0.057(3) 0.064(4) 0.004(3) 0.015(3) -0.002(3)
C22 0.078(4) 0.053(3) 0.067(4) 0.002(3) 0.015(3) 0.004(3)
C23 0.075(4) 0.045(3) 0.063(3) 0.006(2) 0.019(3) 0.006(3)
C24 0.093(5) 0.091(4) 0.066(3) 0.000(3) 0.027(3) 0.027(4)
C25 0.101(5) 0.082(4) 0.072(4) -0.005(3) 0.005(4) -0.002(3)
C26 0.085(4) 0.076(4) 0.083(4) 0.000(3) 0.020(3) 0.019(3)
N3 0.072(3) 0.047(2) 0.049(2) 0.0014(17) 0.021(2) 0.0047(19)
S1 0.0935(11) 0.0444(7) 0.0644(8) -0.0040(6) 0.0328(8) -0.0052(7)

_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
B1 C18 1.628(8) . ?
B1 C9 1.630(8) . ?
B1 C6 1.630(7) 3_655 ?
B1 N3 1.704(6) . ?
C1 C2 1.382(7) . ?
C1 C6 1.397(6) . ?
C1 H1 0.9300 . ?
C2 C3 1.371(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.375(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.389(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.403(6) . ?
C5 C7 1.450(6) . ?
C6 B1 1.630(7) 3_655 ?
C7 N3 1.335(5) 3_655 ?
C7 S1 1.712(4) . ?
C8 C8 1.371(8) 3_655 ?
C8 N3 1.378(5) . ?
C8 S1 1.725(4) . ?
C9 C10 1.407(6) . ?
C9 C14 1.428(7) . ?
C10 C11 1.393(7) . ?
C10 C15 1.519(7) . ?
C11 C12 1.373(8) . ?
C11 H11 0.9300 . ?
C12 C13 1.387(7) . ?
C12 C16 1.512(7) . ?
C13 C14 1.389(7) . ?
C13 H13 0.9300 . ?
C14 C17 1.517(7) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C23 1.413(7) . ?
C18 C19 1.425(6) . ?
C19 C20 1.401(7) . ?
C19 C24 1.515(7) . ?
C20 C21 1.380(7) . ?
C20 H20 0.9300 . ?
C21 C22 1.378(7) . ?
C21 C25 1.514(7) . ?
C22 C23 1.395(7) . ?
C22 H22 0.9300 . ?
C23 C26 1.512(6) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
N3 C7 1.335(5) 3_655 ?

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
C18 B1 C9 116.5(4) . . ?
C18 B1 C6 102.9(4) . 3_655 ?
C9 B1 C6 124.7(5) . 3_655 ?
C18 B1 N3 117.6(4) . . ?
C9 B1 N3 100.0(4) . . ?
C6 B1 N3 93.8(3) 3_655 . ?
C2 C1 C6 121.3(5) . . ?
C2 C1 H1 119.3 . . ?
C6 C1 H1 119.3 . . ?
C3 C2 C1 121.5(5) . . ?
C3 C2 H2 119.2 . . ?
C1 C2 H2 119.2 . . ?
C2 C3 C4 120.0(5) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C3 C4 C5 117.7(5) . . ?
C3 C4 H4 121.2 . . ?
C5 C4 H4 121.2 . . ?
C4 C5 C6 124.6(4) . . ?
C4 C5 C7 126.5(4) . . ?
C6 C5 C7 108.8(4) . . ?
C1 C6 C5 114.8(4) . . ?
C1 C6 B1 131.8(4) . 3_655 ?
C5 C6 B1 112.8(4) . 3_655 ?
N3 C7 C5 113.2(4) 3_655 . ?
N3 C7 S1 115.8(3) 3_655 . ?
C5 C7 S1 131.0(3) . . ?
C8 C8 N3 114.8(5) 3_655 . ?
C8 C8 S1 110.8(4) 3_655 . ?
N3 C8 S1 134.3(3) . . ?
C10 C9 C14 116.1(5) . . ?
C10 C9 B1 120.6(5) . . ?
C14 C9 B1 123.2(5) . . ?
C11 C10 C9 121.0(6) . . ?
C11 C10 C15 115.1(5) . . ?
C9 C10 C15 123.8(5) . . ?
C12 C11 C10 122.7(5) . . ?
C12 C11 H11 118.6 . . ?
C10 C11 H11 118.6 . . ?
C11 C12 C13 117.1(5) . . ?
C11 C12 C16 121.5(6) . . ?
C13 C12 C16 121.4(6) . . ?
C12 C13 C14 122.2(6) . . ?
C12 C13 H13 118.9 . . ?
C14 C13 H13 118.9 . . ?
C13 C14 C9 120.8(5) . . ?
C13 C14 C17 116.5(6) . . ?
C9 C14 C17 122.6(5) . . ?
C10 C15 H15A 109.5 . . ?
C10 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C10 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C12 C16 H16A 109.5 . . ?
C12 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C12 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C23 C18 C19 116.3(5) . . ?
C23 C18 B1 126.7(4) . . ?
C19 C18 B1 116.5(5) . . ?
C20 C19 C18 120.6(5) . . ?
C20 C19 C24 115.2(4) . . ?
C18 C19 C24 124.2(5) . . ?
C21 C20 C19 122.3(5) . . ?
C21 C20 H20 118.9 . . ?
C19 C20 H20 118.9 . . ?
C22 C21 C20 117.3(5) . . ?
C22 C21 C25 122.5(6) . . ?
C20 C21 C25 120.3(5) . . ?
C21 C22 C23 122.7(5) . . ?
C21 C22 H22 118.6 . . ?
C23 C22 H22 118.6 . . ?
C22 C23 C18 120.8(5) . . ?
C22 C23 C26 115.8(5) . . ?
C18 C23 C26 123.4(5) . . ?
C19 C24 H24A 109.5 . . ?
C19 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C19 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C21 C25 H25A 109.5 . . ?
C21 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C21 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C23 C26 H26A 109.5 . . ?
C23 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C23 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C7 N3 C8 109.7(4) 3_655 . ?
C7 N3 B1 110.9(3) 3_655 . ?
C8 N3 B1 138.6(3) . . ?
C7 S1 C8 88.8(2) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.050

###End

data_5
_database_code_depnum_ccdc_archive 'CCDC 794634'
#TrackingRef '- 3 and 5.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H10 N2 S2'
_chemical_formula_weight         294.40

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   P21/c

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

_cell_length_a                   5.735(4)
_cell_length_b                   5.124(3)
_cell_length_c                   23.1380(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.01(3)
_cell_angle_gamma                90.00
_cell_volume                     667.5(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1529
_cell_measurement_theta_min      3.59
_cell_measurement_theta_max      27.45

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.465
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             304
_exptl_absorpt_coefficient_mu    0.388
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.9513
_exptl_absorpt_correction_T_max  0.9586
_exptl_absorpt_process_details   'Higashi (1995)'

_exptl_special_details           
;
?
;

_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  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       'Omega scan'
_diffrn_detector_area_resol_mean 10.0
_diffrn_standards_number         none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        none
_diffrn_reflns_number            6138
_diffrn_reflns_av_R_equivalents  0.0174
_diffrn_reflns_av_sigmaI/netI    0.0151
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         3.59
_diffrn_reflns_theta_max         27.45
_reflns_number_total             1529
_reflns_number_gt                1336
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'RAPID-AUTO (Rigaku, 1998)'
_computing_cell_refinement       RAPID-AUTO
_computing_data_reduction        RAPID-AUTO
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics    SHELXP97
_computing_publication_material  SHELXL97

_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.
;

_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^)+(0.0745P)^2^+0.1595P] 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       0
_refine_ls_number_reflns         1529
_refine_ls_number_parameters     91
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0395
_refine_ls_wR_factor_ref         0.1176
_refine_ls_wR_factor_gt          0.1135
_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 0.70755(7) 0.76293(9) 0.984715(19) 0.04279(19) Uani 1 1 d . . .
N1 N 1.0778(3) 0.8516(3) 0.93546(6) 0.0402(3) Uani 1 1 d . . .
C1 C 0.9479(3) 0.4750(4) 0.84219(8) 0.0471(4) Uani 1 1 d . . .
H1 H 1.0824 0.5769 0.8426 0.057 Uiso 1 1 calc R . .
C2 C 0.8849(4) 0.2864(4) 0.79903(9) 0.0555(5) Uani 1 1 d . . .
H2 H 0.9776 0.2627 0.7706 0.067 Uiso 1 1 calc R . .
C3 C 0.6858(4) 0.1333(4) 0.79793(9) 0.0548(5) Uani 1 1 d . . .
H3 H 0.6450 0.0070 0.7689 0.066 Uiso 1 1 calc R . .
C4 C 0.5488(4) 0.1683(4) 0.83968(9) 0.0548(5) Uani 1 1 d . . .
H4 H 0.4150 0.0650 0.8391 0.066 Uiso 1 1 calc R . .
C5 C 0.6089(3) 0.3573(4) 0.88286(8) 0.0482(4) Uani 1 1 d . . .
H5 H 0.5138 0.3811 0.9108 0.058 Uiso 1 1 calc R . .
C6 C 0.8097(3) 0.5114(3) 0.88481(7) 0.0368(4) Uani 1 1 d . . .
C7 C 0.8817(3) 0.7084(3) 0.93099(7) 0.0345(3) Uani 1 1 d . . .
C8 C 0.9109(3) 0.9911(3) 1.01589(6) 0.0359(4) Uani 1 1 d . . .

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 0.0378(3) 0.0492(3) 0.0449(3) -0.00335(16) 0.01706(19) -0.00760(16)
N1 0.0416(7) 0.0443(8) 0.0350(6) -0.0017(6) 0.0082(6) 0.0039(6)
C1 0.0482(9) 0.0483(10) 0.0483(9) -0.0035(8) 0.0178(7) -0.0033(8)
C2 0.0643(13) 0.0557(11) 0.0498(10) -0.0096(8) 0.0196(9) 0.0020(9)
C3 0.0622(12) 0.0465(10) 0.0520(10) -0.0089(8) 0.0013(9) 0.0036(9)
C4 0.0480(10) 0.0512(10) 0.0623(12) -0.0019(9) 0.0032(9) -0.0087(9)
C5 0.0441(9) 0.0532(10) 0.0480(9) -0.0010(8) 0.0108(7) -0.0053(8)
C6 0.0371(8) 0.0376(8) 0.0358(7) 0.0048(6) 0.0074(6) 0.0042(6)
C7 0.0314(7) 0.0387(8) 0.0349(7) 0.0053(6) 0.0101(6) 0.0023(6)
C8 0.0314(7) 0.0411(8) 0.0367(7) 0.0040(6) 0.0103(6) -0.0006(6)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C8 1.7105(19) . ?
S1 C7 1.7593(17) . ?
N1 C7 1.330(2) . ?
N1 C8 1.376(2) 3_777 ?
C1 C2 1.387(3) . ?
C1 C6 1.391(2) . ?
C1 H1 0.9300 . ?
C2 C3 1.381(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.368(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.387(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.390(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.471(2) . ?
C8 C8 1.372(3) 3_777 ?
C8 N1 1.376(2) 3_777 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 S1 C7 88.46(8) . . ?
C7 N1 C8 107.10(14) . 3_777 ?
C2 C1 C6 119.89(18) . . ?
C2 C1 H1 120.1 . . ?
C6 C1 H1 120.1 . . ?
C3 C2 C1 120.65(19) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C4 C3 C2 119.78(19) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C5 120.19(19) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C4 C5 C6 120.69(18) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C5 C6 C1 118.79(17) . . ?
C5 C6 C7 121.97(15) . . ?
C1 C6 C7 119.23(16) . . ?
N1 C7 C6 123.44(14) . . ?
N1 C7 S1 116.30(13) . . ?
C6 C7 S1 120.26(12) . . ?
C8 C8 N1 118.42(19) 3_777 3_777 ?
C8 C8 S1 109.71(16) 3_777 . ?
N1 C8 S1 131.87(12) 3_777 . ?

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
C6 C1 C2 C3 -0.1(3) . . . . ?
C1 C2 C3 C4 0.2(3) . . . . ?
C2 C3 C4 C5 0.2(3) . . . . ?
C3 C4 C5 C6 -0.7(3) . . . . ?
C4 C5 C6 C1 0.8(3) . . . . ?
C4 C5 C6 C7 -178.29(17) . . . . ?
C2 C1 C6 C5 -0.4(3) . . . . ?
C2 C1 C6 C7 178.73(16) . . . . ?
C8 N1 C7 C6 -178.77(14) 3_777 . . . ?
C8 N1 C7 S1 0.54(17) 3_777 . . . ?
C5 C6 C7 N1 177.23(16) . . . . ?
C1 C6 C7 N1 -1.9(2) . . . . ?
C5 C6 C7 S1 -2.1(2) . . . . ?
C1 C6 C7 S1 178.86(13) . . . . ?
C8 S1 C7 N1 -0.47(13) . . . . ?
C8 S1 C7 C6 178.86(13) . . . . ?
C7 S1 C8 C8 0.24(16) . . . 3_777 ?
C7 S1 C8 N1 -179.75(16) . . . 3_777 ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.45
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.458
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.064