# Electronic Supplementary Material for CrystEngComm
# This journal is (c) The Royal Society of Chemistry 2009

data_global
_journal_name_full               CrystEngComm

_journal_coden_Cambridge         1350

_publ_contact_author_name        'Chen-Jie Fang'
_publ_contact_author_email       CJFANG@CCMU.EDU.CN

_publ_section_title              
;
An enhanced fluorescence in a tunable
face-to-face pi-pi stacking assembly directed by the H-bonding
;
loop_
_publ_author_name
'Chen-Jie Fang'
'Xiao-Fei Fu'
'Rui Guo'
'Le-Le Li'
'Wei Sun'
'Chun-Hu Xu'
'Chunhua Yan'
'Yan-Feng Yue'

# Attachment 'B910263A.CIF'

data_1
_database_code_depnum_ccdc_archive 'CCDC 721344'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H17 N3 S'
_chemical_formula_weight         307.41

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   P2(1)/n

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

_cell_length_a                   20.622(4)
_cell_length_b                   7.3581(15)
_cell_length_c                   21.626(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.42(3)
_cell_angle_gamma                90.00
_cell_volume                     3191.8(11)
_cell_formula_units_Z            8
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    21988
_cell_measurement_theta_min      3.395
_cell_measurement_theta_max      27.485

_exptl_crystal_description       rod-like
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1296
_exptl_absorpt_coefficient_mu    0.203
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.891
_exptl_absorpt_correction_T_max  0.979
_exptl_absorpt_process_details   
;
multi-scan from symmetry-related measurements
Sortav (Blessing 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  'NONIUS KappaCCD Diffractometer'
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean 0.77
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            48641
_diffrn_reflns_av_R_equivalents  0.0660
_diffrn_reflns_av_sigmaI/netI    0.0615
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         3.40
_diffrn_reflns_theta_max         27.51
_reflns_number_total             7322
_reflns_number_gt                3675
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'KappaCCD (Nonius B. V., 1998)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor, 1997)'
_computing_data_reduction        
'HKL Denzo (Otwinowski & Minor, 1997) & maXus (Mackay et al., 1998)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL V5.1 (Sheldrick, 1998)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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)+(0.0521P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7322
_refine_ls_number_parameters     524
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1081
_refine_ls_R_factor_gt           0.0394
_refine_ls_wR_factor_ref         0.1016
_refine_ls_wR_factor_gt          0.0856
_refine_ls_goodness_of_fit_ref   0.905
_refine_ls_restrained_S_all      0.905
_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
C1 C 0.61793(13) 0.7258(4) 0.00862(11) 0.0810(6) Uani 1 1 d . . .
H1A H 0.6547(10) 0.809(3) 0.0310(9) 0.096(7) Uiso 1 1 d . . .
H1B H 0.6394(10) 0.596(3) 0.0061(9) 0.124(8) Uiso 1 1 d . . .
H1C H 0.5994(10) 0.769(3) -0.0349(10) 0.107(7) Uiso 1 1 d . . .
C2 C 0.56421(10) 0.7229(3) 0.04488(9) 0.0696(5) Uani 1 1 d . . .
H2A H 0.5431(8) 0.841(2) 0.0471(7) 0.074(6) Uiso 1 1 d . . .
H2B H 0.5299(8) 0.637(2) 0.0254(7) 0.066(5) Uiso 1 1 d . . .
C3 C 0.55646(8) 0.6050(2) 0.15009(8) 0.0526(4) Uani 1 1 d . . .
C4 C 0.68997(8) 0.5266(2) 0.27959(8) 0.0499(4) Uani 1 1 d . . .
H4 H 0.6666(7) 0.4593(19) 0.3066(7) 0.057(5) Uiso 1 1 d . . .
C5 C 0.76104(7) 0.55884(18) 0.30561(7) 0.0449(4) Uani 1 1 d . . .
C6 C 0.80772(8) 0.55703(19) 0.26675(7) 0.0469(4) Uani 1 1 d . . .
C7 C 0.79198(10) 0.5068(2) 0.20149(8) 0.0570(4) Uani 1 1 d . . .
H7 H 0.7474(8) 0.4722(19) 0.1822(7) 0.052(5) Uiso 1 1 d . . .
C8 C 0.83953(11) 0.5030(3) 0.16719(10) 0.0709(5) Uani 1 1 d . . .
H8 H 0.8266(8) 0.467(2) 0.1224(9) 0.077(6) Uiso 1 1 d . . .
C9 C 0.90580(12) 0.5522(3) 0.19495(12) 0.0794(6) Uani 1 1 d . . .
H9 H 0.9373(10) 0.554(2) 0.1699(9) 0.094(7) Uiso 1 1 d . . .
C10 C 0.92317(11) 0.6009(3) 0.25618(11) 0.0723(5) Uani 1 1 d . . .
H10 H 0.9667(9) 0.634(2) 0.2774(8) 0.085(6) Uiso 1 1 d . . .
C11 C 0.87589(8) 0.6041(2) 0.29470(8) 0.0533(4) Uani 1 1 d . . .
C12 C 0.89417(9) 0.6531(2) 0.35840(9) 0.0576(5) Uani 1 1 d . . .
H12 H 0.9394(8) 0.688(2) 0.3778(7) 0.070(5) Uiso 1 1 d . . .
C13 C 0.84962(8) 0.6525(2) 0.39720(8) 0.0512(4) Uani 1 1 d . . .
C14 C 0.86887(11) 0.7052(2) 0.46252(9) 0.0639(5) Uani 1 1 d . . .
H14 H 0.9120(9) 0.740(2) 0.4755(7) 0.069(5) Uiso 1 1 d . . .
C15 C 0.82562(12) 0.7044(3) 0.50009(10) 0.0731(6) Uani 1 1 d . . .
H15 H 0.8406(8) 0.737(2) 0.5434(8) 0.079(6) Uiso 1 1 d . . .
C16 C 0.75958(11) 0.6493(3) 0.47522(9) 0.0728(6) Uani 1 1 d . . .
H16 H 0.7297(9) 0.653(3) 0.5027(9) 0.098(7) Uiso 1 1 d . . .
C17 C 0.73815(10) 0.6010(2) 0.41351(9) 0.0618(5) Uani 1 1 d . . .
H17 H 0.6907(9) 0.566(2) 0.3955(8) 0.076(5) Uiso 1 1 d . . .
C18 C 0.78199(7) 0.5999(2) 0.37119(7) 0.0476(4) Uani 1 1 d . . .
C19 C 0.40364(11) 0.3140(3) 0.46884(9) 0.0820(6) Uani 1 1 d . . .
H19A H 0.3679 0.2337 0.4499 0.085(6) Uiso 1 1 calc R . .
H19B H 0.3866 0.4352 0.4699 0.117(8) Uiso 1 1 calc R . .
H19C H 0.4233 0.2746 0.5114 0.114(8) Uiso 1 1 calc R . .
C20 C 0.45543(11) 0.3121(4) 0.43024(9) 0.0729(6) Uani 1 1 d . . .
H20A H 0.4871(9) 0.402(2) 0.4450(8) 0.077(6) Uiso 1 1 d . . .
H20B H 0.4746(9) 0.190(3) 0.4305(8) 0.089(7) Uiso 1 1 d . . .
C21 C 0.45570(8) 0.4405(2) 0.32457(8) 0.0516(4) Uani 1 1 d . . .
C22 C 0.31284(8) 0.4910(2) 0.20278(8) 0.0499(4) Uani 1 1 d . . .
H22 H 0.3297(7) 0.5563(19) 0.1730(7) 0.054(5) Uiso 1 1 d . . .
C23 C 0.24099(7) 0.45780(18) 0.18777(7) 0.0436(4) Uani 1 1 d . . .
C24 C 0.20391(8) 0.46080(18) 0.23551(7) 0.0443(4) Uani 1 1 d . . .
C25 C 0.23099(10) 0.5075(2) 0.30017(8) 0.0538(4) Uani 1 1 d . . .
H25 H 0.2747(8) 0.5377(19) 0.3132(7) 0.050(5) Uiso 1 1 d . . .
C26 C 0.19320(10) 0.5097(2) 0.34369(9) 0.0646(5) Uani 1 1 d . . .
H26 H 0.2144(7) 0.5460(19) 0.3881(7) 0.060(5) Uiso 1 1 d . . .
C27 C 0.12459(11) 0.4653(3) 0.32607(10) 0.0708(6) Uani 1 1 d . . .
H27 H 0.0998(8) 0.469(2) 0.3576(8) 0.071(5) Uiso 1 1 d . . .
C28 C 0.09646(10) 0.4230(2) 0.26551(10) 0.0637(5) Uani 1 1 d . . .
H28 H 0.0509(9) 0.390(2) 0.2539(8) 0.077(6) Uiso 1 1 d . . .
C29 C 0.13406(8) 0.41981(19) 0.21826(8) 0.0491(4) Uani 1 1 d . . .
C30 C 0.10421(9) 0.3751(2) 0.15571(8) 0.0547(4) Uani 1 1 d . . .
H30 H 0.0582(8) 0.3416(18) 0.1455(7) 0.056(4) Uiso 1 1 d . . .
C31 C 0.13932(8) 0.3732(2) 0.10851(7) 0.0492(4) Uani 1 1 d . . .
C32 C 0.10793(11) 0.3261(2) 0.04457(9) 0.0642(5) Uani 1 1 d . . .
H32 H 0.0628(8) 0.297(2) 0.0384(7) 0.070(5) Uiso 1 1 d . . .
C33 C 0.14209(11) 0.3213(3) -0.00125(9) 0.0719(6) Uani 1 1 d . . .
H33 H 0.1210(8) 0.288(2) -0.0428(8) 0.079(6) Uiso 1 1 d . . .
C34 C 0.21035(11) 0.3659(3) 0.01344(9) 0.0690(5) Uani 1 1 d . . .
H34 H 0.2356(8) 0.358(2) -0.0192(8) 0.071(5) Uiso 1 1 d . . .
C35 C 0.24240(10) 0.4107(2) 0.07363(8) 0.0586(5) Uani 1 1 d . . .
H35 H 0.2892(8) 0.4366(19) 0.0824(7) 0.059(5) Uiso 1 1 d . . .
C36 C 0.20875(7) 0.41828(19) 0.12404(7) 0.0449(4) Uani 1 1 d . . .
N1 N 0.59151(8) 0.6678(2) 0.11061(7) 0.0623(4) Uani 1 1 d . . .
H1D H 0.6334(9) 0.685(2) 0.1272(8) 0.077(6) Uiso 1 1 d . . .
N2 N 0.59196(7) 0.5599(2) 0.20861(7) 0.0554(4) Uani 1 1 d . . .
H2D H 0.5737(8) 0.526(2) 0.2350(7) 0.046(5) Uiso 1 1 d . . .
N3 N 0.65950(6) 0.58716(16) 0.22519(6) 0.0520(3) Uani 1 1 d . . .
N4 N 0.42544(8) 0.3580(2) 0.36450(7) 0.0668(5) Uani 1 1 d . . .
H4D H 0.3864(8) 0.327(2) 0.3486(7) 0.058(5) Uiso 1 1 d . . .
N5 N 0.41705(7) 0.4707(2) 0.26581(7) 0.0558(4) Uani 1 1 d . . .
H5D H 0.4316(8) 0.524(2) 0.2385(8) 0.058(6) Uiso 1 1 d . . .
N6 N 0.35048(6) 0.43122(16) 0.25435(6) 0.0523(3) Uani 1 1 d . . .
S1 S 0.47373(2) 0.57202(8) 0.13050(2) 0.08052(19) Uani 1 1 d . . .
S2 S 0.53494(2) 0.51246(7) 0.34370(2) 0.07138(17) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.499(3) . ?
C1 H1A 1.01(2) . ?
C1 H1B 1.06(2) . ?
C1 H1C 0.984(19) . ?
C2 N1 1.459(2) . ?
C2 H2A 0.981(17) . ?
C2 H2B 0.969(17) . ?
C3 N1 1.323(2) . ?
C3 N2 1.348(2) . ?
C3 S1 1.6773(17) . ?
C4 N3 1.2785(19) . ?
C4 C5 1.462(2) . ?
C4 H4 0.975(15) . ?
C5 C18 1.416(2) . ?
C5 C6 1.417(2) . ?
C6 C7 1.422(2) . ?
C6 C11 1.438(2) . ?
C7 C8 1.360(3) . ?
C7 H7 0.952(15) . ?
C8 C9 1.407(3) . ?
C8 H8 0.980(17) . ?
C9 C10 1.338(3) . ?
C9 H9 0.937(19) . ?
C10 C11 1.422(2) . ?
C10 H10 0.940(18) . ?
C11 C12 1.389(2) . ?
C12 C13 1.381(2) . ?
C12 H12 0.966(16) . ?
C13 C14 1.429(2) . ?
C13 C18 1.431(2) . ?
C14 C15 1.339(3) . ?
C14 H14 0.903(16) . ?
C15 C16 1.403(3) . ?
C15 H15 0.947(16) . ?
C16 C17 1.352(2) . ?
C16 H16 0.951(18) . ?
C17 C18 1.428(2) . ?
C17 H17 0.999(17) . ?
C19 C20 1.500(3) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 N4 1.452(2) . ?
C20 H20A 0.930(18) . ?
C20 H20B 0.984(18) . ?
C21 N4 1.324(2) . ?
C21 N5 1.3524(19) . ?
C21 S2 1.6756(17) . ?
C22 N6 1.2798(19) . ?
C22 C23 1.462(2) . ?
C22 H22 0.932(15) . ?
C23 C36 1.415(2) . ?
C23 C24 1.420(2) . ?
C24 C25 1.422(2) . ?
C24 C29 1.434(2) . ?
C25 C26 1.354(2) . ?
C25 H25 0.907(15) . ?
C26 C27 1.415(3) . ?
C26 H26 0.995(15) . ?
C27 C28 1.340(3) . ?
C27 H27 0.944(17) . ?
C28 C29 1.419(2) . ?
C28 H28 0.945(17) . ?
C29 C30 1.390(2) . ?
C30 C31 1.382(2) . ?
C30 H30 0.955(15) . ?
C31 C32 1.427(2) . ?
C31 C36 1.432(2) . ?
C32 C33 1.343(3) . ?
C32 H32 0.933(16) . ?
C33 C34 1.408(3) . ?
C33 H33 0.935(16) . ?
C34 C35 1.357(2) . ?
C34 H34 0.971(15) . ?
C35 C36 1.423(2) . ?
C35 H35 0.959(15) . ?
N1 H1D 0.865(17) . ?
N2 N3 1.3700(17) . ?
N2 H2D 0.794(14) . ?
N4 H4D 0.829(15) . ?
N5 N6 1.3684(17) . ?
N5 H5D 0.822(15) . ?

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 C1 H1A 108.8(10) . . ?
C2 C1 H1B 112.6(11) . . ?
H1A C1 H1B 107.1(16) . . ?
C2 C1 H1C 109.7(12) . . ?
H1A C1 H1C 110.2(16) . . ?
H1B C1 H1C 108.4(16) . . ?
N1 C2 C1 110.42(18) . . ?
N1 C2 H2A 105.9(10) . . ?
C1 C2 H2A 113.8(10) . . ?
N1 C2 H2B 108.7(9) . . ?
C1 C2 H2B 109.7(9) . . ?
H2A C2 H2B 108.2(14) . . ?
N1 C3 N2 115.64(15) . . ?
N1 C3 S1 124.29(14) . . ?
N2 C3 S1 120.02(14) . . ?
N3 C4 C5 122.14(16) . . ?
N3 C4 H4 121.6(9) . . ?
C5 C4 H4 116.3(9) . . ?
C18 C5 C6 120.30(14) . . ?
C18 C5 C4 117.75(14) . . ?
C6 C5 C4 121.90(14) . . ?
C5 C6 C7 124.13(15) . . ?
C5 C6 C11 118.74(14) . . ?
C7 C6 C11 117.11(16) . . ?
C8 C7 C6 121.29(19) . . ?
C8 C7 H7 120.0(9) . . ?
C6 C7 H7 118.6(9) . . ?
C7 C8 C9 120.9(2) . . ?
C7 C8 H8 118.7(10) . . ?
C9 C8 H8 120.3(10) . . ?
C10 C9 C8 120.1(2) . . ?
C10 C9 H9 120.4(12) . . ?
C8 C9 H9 119.5(12) . . ?
C9 C10 C11 121.5(2) . . ?
C9 C10 H10 123.9(11) . . ?
C11 C10 H10 114.6(11) . . ?
C12 C11 C10 121.34(17) . . ?
C12 C11 C6 119.57(16) . . ?
C10 C11 C6 119.09(17) . . ?
C13 C12 C11 122.43(16) . . ?
C13 C12 H12 116.7(9) . . ?
C11 C12 H12 120.9(9) . . ?
C12 C13 C14 121.90(16) . . ?
C12 C13 C18 119.17(15) . . ?
C14 C13 C18 118.92(17) . . ?
C15 C14 C13 121.83(19) . . ?
C15 C14 H14 124.0(11) . . ?
C13 C14 H14 114.2(11) . . ?
C14 C15 C16 119.52(19) . . ?
C14 C15 H15 119.3(10) . . ?
C16 C15 H15 121.1(10) . . ?
C17 C16 C15 121.3(2) . . ?
C17 C16 H16 120.9(12) . . ?
C15 C16 H16 117.7(12) . . ?
C16 C17 C18 121.55(19) . . ?
C16 C17 H17 121.2(10) . . ?
C18 C17 H17 117.3(10) . . ?
C5 C18 C17 123.48(15) . . ?
C5 C18 C13 119.64(14) . . ?
C17 C18 C13 116.81(15) . . ?
C20 C19 H19A 109.5 . . ?
C20 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C20 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N4 C20 C19 110.25(17) . . ?
N4 C20 H20A 106.0(11) . . ?
C19 C20 H20A 109.6(11) . . ?
N4 C20 H20B 107.3(10) . . ?
C19 C20 H20B 110.1(11) . . ?
H20A C20 H20B 113.4(15) . . ?
N4 C21 N5 115.08(15) . . ?
N4 C21 S2 124.33(13) . . ?
N5 C21 S2 120.55(14) . . ?
N6 C22 C23 120.96(16) . . ?
N6 C22 H22 122.1(9) . . ?
C23 C22 H22 117.0(9) . . ?
C36 C23 C24 120.05(14) . . ?
C36 C23 C22 118.28(14) . . ?
C24 C23 C22 121.66(14) . . ?
C23 C24 C25 124.31(14) . . ?
C23 C24 C29 119.05(14) . . ?
C25 C24 C29 116.62(15) . . ?
C26 C25 C24 121.89(18) . . ?
C26 C25 H25 118.2(9) . . ?
C24 C25 H25 119.9(9) . . ?
C25 C26 C27 120.71(19) . . ?
C25 C26 H26 118.7(9) . . ?
C27 C26 H26 120.6(9) . . ?
C28 C27 C26 119.72(19) . . ?
C28 C27 H27 121.9(10) . . ?
C26 C27 H27 118.4(10) . . ?
C27 C28 C29 121.50(19) . . ?
C27 C28 H28 119.8(10) . . ?
C29 C28 H28 118.7(10) . . ?
C30 C29 C28 120.81(16) . . ?
C30 C29 C24 119.64(15) . . ?
C28 C29 C24 119.55(16) . . ?
C31 C30 C29 122.12(16) . . ?
C31 C30 H30 119.2(9) . . ?
C29 C30 H30 118.6(9) . . ?
C30 C31 C32 121.38(16) . . ?
C30 C31 C36 119.44(14) . . ?
C32 C31 C36 119.18(16) . . ?
C33 C32 C31 121.60(19) . . ?
C33 C32 H32 124.3(10) . . ?
C31 C32 H32 114.1(10) . . ?
C32 C33 C34 119.70(19) . . ?
C32 C33 H33 120.5(11) . . ?
C34 C33 H33 119.8(11) . . ?
C35 C34 C33 120.8(2) . . ?
C35 C34 H34 119.3(10) . . ?
C33 C34 H34 119.8(10) . . ?
C34 C35 C36 121.95(18) . . ?
C34 C35 H35 118.9(9) . . ?
C36 C35 H35 119.2(9) . . ?
C23 C36 C35 123.51(14) . . ?
C23 C36 C31 119.64(14) . . ?
C35 C36 C31 116.76(15) . . ?
C3 N1 C2 125.47(16) . . ?
C3 N1 H1D 115.3(11) . . ?
C2 N1 H1D 119.0(11) . . ?
C3 N2 N3 120.48(15) . . ?
C3 N2 H2D 120.5(12) . . ?
N3 N2 H2D 118.8(12) . . ?
C4 N3 N2 116.26(14) . . ?
C21 N4 C20 125.93(17) . . ?
C21 N4 H4D 114.4(11) . . ?
C20 N4 H4D 119.6(11) . . ?
C21 N5 N6 118.88(15) . . ?
C21 N5 H5D 121.3(12) . . ?
N6 N5 H5D 119.3(12) . . ?
C22 N6 N5 117.71(14) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2D S2 0.794(14) 2.655(15) 3.4109(19) 159.8(14) .
N5 H5D S1 0.822(15) 2.697(16) 3.4745(18) 158.6(14) .

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.51
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.032

data_2
_database_code_depnum_ccdc_archive 'CCDC 721345'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C37 H38 N6 O S2'
_chemical_formula_weight         646.85

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'
O O 0.0106 0.0060 '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

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                   18.946(4)
_cell_length_b                   8.8906(18)
_cell_length_c                   20.698(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.51(3)
_cell_angle_gamma                90.00
_cell_volume                     3375.1(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3254
_cell_measurement_theta_min      2.221
_cell_measurement_theta_max      24.891

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1368
_exptl_absorpt_coefficient_mu    0.197
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.821193
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_process_details   ?

_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  'Bruker SMART APEX-CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 15X15microns
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9169
_diffrn_reflns_av_R_equivalents  0.0276
_diffrn_reflns_av_sigmaI/netI    0.0278
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.03
_diffrn_reflns_theta_max         25.06
_reflns_number_total             2985
_reflns_number_gt                2535
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
'SMART :BRUKER MOLECULAR ANALYSIS Research ToolV5.618 Copyr.1997-00 BrukerAXS'
_computing_cell_refinement       
'SMART :BRUKER MOLECULAR ANALYSIS Research ToolV5.618 Copyr.1997-00 BrukerAXS'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL V5.1 (Sheldrick, 1998)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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.

The four hydrogen atoms belonging to this methanol molecule have not been
included in the refinement due to the disorder of the solvent molecule.The
bond lengths of C(19)-O(2) and C(19)-O(1) is rather short, which may be
caused by the H-bonding interations of this group, therefore,restraint DFIX
was used in order to control the geometry. The H-bonds may be affected by
the disorder of the methanol molecule.
;

_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)+(0.0638P)²+2.0864P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2985
_refine_ls_number_parameters     285
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0625
_refine_ls_R_factor_gt           0.0531
_refine_ls_wR_factor_ref         0.1371
_refine_ls_wR_factor_gt          0.1319
_refine_ls_goodness_of_fit_ref   1.146
_refine_ls_restrained_S_all      1.158
_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
C1 C 0.3294(2) 0.4408(5) 0.36240(19) 0.0827(11) Uani 1 1 d . . .
H1A H 0.297(3) 0.422(5) 0.396(2) 0.137(17) Uiso 1 1 d . . .
H1B H 0.3215(18) 0.550(4) 0.3468(16) 0.085(10) Uiso 1 1 d . . .
H1C H 0.378(2) 0.430(4) 0.3838(19) 0.097(12) Uiso 1 1 d . . .
C2 C 0.31400(15) 0.3356(4) 0.30427(15) 0.0590(7) Uani 1 1 d . . .
H2A H 0.3189(15) 0.233(3) 0.3207(14) 0.069(8) Uiso 1 1 d . . .
H2B H 0.3450(18) 0.349(4) 0.2775(17) 0.085(11) Uiso 1 1 d . . .
C3 C 0.18433(13) 0.2692(3) 0.26743(11) 0.0414(5) Uani 1 1 d . . .
C4 C 0.04317(14) 0.4502(3) 0.15220(12) 0.0450(6) Uani 1 1 d . . .
H4 H 0.0061(15) 0.387(3) 0.1576(13) 0.056(7) Uiso 1 1 d . . .
C5 C 0.01967(13) 0.5739(3) 0.10495(11) 0.0430(5) Uani 1 1 d . . .
C6 C 0.06007(14) 0.6184(3) 0.05900(11) 0.0464(6) Uani 1 1 d . . .
C7 C 0.12715(15) 0.5539(3) 0.05551(13) 0.0542(7) Uani 1 1 d . . .
H7 H 0.1460(14) 0.477(3) 0.0838(13) 0.052(7) Uiso 1 1 d . . .
C8 C 0.16370(19) 0.6009(4) 0.01088(15) 0.0674(8) Uani 1 1 d . . .
H8 H 0.207(2) 0.555(4) 0.0062(18) 0.095(12) Uiso 1 1 d . . .
C9 C 0.1357(2) 0.7163(4) -0.03444(16) 0.0741(10) Uani 1 1 d . . .
H9 H 0.1624(18) 0.745(4) -0.0621(17) 0.083(10) Uiso 1 1 d . . .
C10 C 0.0722(2) 0.7794(4) -0.03451(14) 0.0672(9) Uani 1 1 d . . .
H10 H 0.0540(16) 0.851(3) -0.0614(15) 0.064(9) Uiso 1 1 d . . .
C11 C 0.03062(15) 0.7344(3) 0.01135(12) 0.0527(7) Uani 1 1 d . . .
C12 C -0.03630(18) 0.7972(3) 0.01086(14) 0.0618(8) Uani 1 1 d . . .
H12 H -0.0541(18) 0.868(4) -0.0174(16) 0.075(9) Uiso 1 1 d . . .
C13 C -0.07695(15) 0.7542(3) 0.05517(14) 0.0567(7) Uani 1 1 d . . .
C14 C -0.14602(19) 0.8187(4) 0.05308(19) 0.0744(9) Uani 1 1 d . . .
H14 H -0.1649(19) 0.894(4) 0.0185(18) 0.091(11) Uiso 1 1 d . . .
C15 C -0.1849(2) 0.7757(4) 0.0964(2) 0.0831(11) Uani 1 1 d . . .
H15 H -0.233(2) 0.812(4) 0.0944(17) 0.101(12) Uiso 1 1 d . . .
C16 C -0.15588(18) 0.6681(4) 0.14627(19) 0.0733(9) Uani 1 1 d . . .
H16 H -0.1837(18) 0.639(4) 0.1766(16) 0.080(10) Uiso 1 1 d . . .
C17 C -0.09020(16) 0.6042(3) 0.14983(15) 0.0593(7) Uani 1 1 d . . .
H17 H -0.0717(15) 0.538(3) 0.1836(14) 0.062(8) Uiso 1 1 d . . .
C18 C -0.04802(14) 0.6416(3) 0.10398(12) 0.0491(6) Uani 1 1 d . . .
N1 N 0.24033(11) 0.3522(2) 0.26215(10) 0.0513(5) Uani 1 1 d D . .
H1D H 0.2315(14) 0.425(2) 0.2347(11) 0.055(8) Uiso 1 1 d D . .
N2 N 0.11819(11) 0.3044(2) 0.22725(10) 0.0484(5) Uani 1 1 d . . .
H2D H 0.0813(16) 0.248(3) 0.2280(13) 0.058 Uiso 1 1 d . . .
N3 N 0.10892(11) 0.4276(2) 0.18562(10) 0.0454(5) Uani 1 1 d . . .
S1 S 0.18918(4) 0.12160(7) 0.31981(3) 0.0503(2) Uani 1 1 d . . .
O1 O 0.0111(8) 0.0952(10) 0.2820(7) 0.060(3) Uani 0.25 1 d PD . .
O2 O 0.0000 0.1088(8) 0.2500 0.113(8) Uani 0.50 2 d SPD . .
C19 C 0.0000 -0.0450(6) 0.2500 0.132(3) Uani 1 2 d SD . .


_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
C1 C2 1.494(5) . ?
C1 H1A 1.05(5) . ?
C1 H1B 1.02(3) . ?
C1 H1C 0.92(4) . ?
C2 N1 1.456(3) . ?
C2 H2A 0.97(3) . ?
C2 H2B 0.91(3) . ?
C3 N1 1.319(3) . ?
C3 N2 1.355(3) . ?
C3 S1 1.690(2) . ?
C4 N3 1.280(3) . ?
C4 C5 1.465(3) . ?
C4 H4 0.93(3) . ?
C5 C18 1.412(3) . ?
C5 C6 1.419(3) . ?
C6 C7 1.413(4) . ?
C6 C11 1.439(3) . ?
C7 C8 1.352(4) . ?
C7 H7 0.91(3) . ?
C8 C9 1.402(5) . ?
C8 H8 0.94(4) . ?
C9 C10 1.328(5) . ?
C9 H9 0.89(3) . ?
C10 C11 1.433(4) . ?
C10 H10 0.86(3) . ?
C11 C12 1.383(4) . ?
C12 C13 1.391(4) . ?
C12 H12 0.87(3) . ?
C13 C14 1.419(4) . ?
C13 C18 1.430(3) . ?
C14 C15 1.352(5) . ?
C14 H14 0.98(4) . ?
C15 C16 1.413(5) . ?
C15 H15 0.97(4) . ?
C16 C17 1.353(4) . ?
C16 H16 0.95(3) . ?
C17 C18 1.425(4) . ?
C17 H17 0.91(3) . ?
N1 H1D 0.851(10) . ?
N2 N3 1.377(3) . ?
N2 H2D 0.86(3) . ?
O1 O2 0.655(13) . ?
O1 O1 1.29(3) 2 ?
O1 C19 1.403(9) . ?
O2 O1 0.655(13) 2 ?
O2 C19 1.368(8) . ?
C19 O1 1.403(9) 2 ?

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 C1 H1A 114(3) . . ?
C2 C1 H1B 110.9(19) . . ?
H1A C1 H1B 107(3) . . ?
C2 C1 H1C 107(2) . . ?
H1A C1 H1C 110(3) . . ?
H1B C1 H1C 108(3) . . ?
N1 C2 C1 112.6(3) . . ?
N1 C2 H2A 107.4(17) . . ?
C1 C2 H2A 108.8(17) . . ?
N1 C2 H2B 107(2) . . ?
C1 C2 H2B 113(2) . . ?
H2A C2 H2B 108(3) . . ?
N1 C3 N2 117.3(2) . . ?
N1 C3 S1 124.87(18) . . ?
N2 C3 S1 117.79(18) . . ?
N3 C4 C5 124.8(2) . . ?
N3 C4 H4 120.2(16) . . ?
C5 C4 H4 115.0(16) . . ?
C18 C5 C6 120.8(2) . . ?
C18 C5 C4 116.9(2) . . ?
C6 C5 C4 122.2(2) . . ?
C7 C6 C5 124.4(2) . . ?
C7 C6 C11 117.1(2) . . ?
C5 C6 C11 118.5(2) . . ?
C8 C7 C6 122.1(3) . . ?
C8 C7 H7 119.0(16) . . ?
C6 C7 H7 118.9(16) . . ?
C7 C8 C9 120.7(3) . . ?
C7 C8 H8 123(2) . . ?
C9 C8 H8 116(2) . . ?
C10 C9 C8 120.1(3) . . ?
C10 C9 H9 123(2) . . ?
C8 C9 H9 117(2) . . ?
C9 C10 C11 122.0(3) . . ?
C9 C10 H10 122(2) . . ?
C11 C10 H10 116(2) . . ?
C12 C11 C10 122.5(3) . . ?
C12 C11 C6 119.4(2) . . ?
C10 C11 C6 118.1(3) . . ?
C11 C12 C13 122.8(3) . . ?
C11 C12 H12 120(2) . . ?
C13 C12 H12 117(2) . . ?
C12 C13 C14 121.8(3) . . ?
C12 C13 C18 118.7(3) . . ?
C14 C13 C18 119.4(3) . . ?
C15 C14 C13 121.2(3) . . ?
C15 C14 H14 121(2) . . ?
C13 C14 H14 118(2) . . ?
C14 C15 C16 119.9(3) . . ?
C14 C15 H15 123(2) . . ?
C16 C15 H15 117(2) . . ?
C17 C16 C15 120.6(3) . . ?
C17 C16 H16 120(2) . . ?
C15 C16 H16 119(2) . . ?
C16 C17 C18 121.8(3) . . ?
C16 C17 H17 118.9(18) . . ?
C18 C17 H17 119.2(18) . . ?
C5 C18 C17 123.4(2) . . ?
C5 C18 C13 119.6(2) . . ?
C17 C18 C13 117.0(2) . . ?
C3 N1 C2 124.4(2) . . ?
C3 N1 H1D 117.1(18) . . ?
C2 N1 H1D 118.3(18) . . ?
C3 N2 N3 121.4(2) . . ?
C3 N2 H2D 118.8(18) . . ?
N3 N2 H2D 119.8(18) . . ?
C4 N3 N2 114.7(2) . . ?
O2 O1 O1 10.7(12) . 2 ?
O2 O1 C19 73.4(12) . . ?
O1 O1 C19 62.7(5) 2 . ?
O1 O2 O1 159(2) 2 . ?
O1 O2 C19 79.3(12) 2 . ?
O1 O2 C19 79.3(12) . . ?
O2 C19 O1 27.3(5) . . ?
O2 C19 O1 27.3(5) . 2 ?
O1 C19 O1 54.6(11) . 2 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2D O2 0.86(3) 2.11(3) 2.965(5) 169(2) .
N2 H2D O1 0.86(3) 2.37(3) 3.164(13) 153(2) .
N2 H2D O1 0.86(3) 2.18(3) 3.044(13) 173(2) 2
N1 H1D S1 0.851(10) 2.726(19) 3.396(2) 137(2) 4
C9 H9 S1 0.89(3) 2.88(3) 3.706(3) 156(3) 6_565

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.06
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.376
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.046


