# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry
# This journal is © The Royal Society of Chemistry 2012


data_global
_journal_name_full               J.Mater.Chem.
_journal_coden_cambridge         1145
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
_publ_contact_author_email       yshxie@ecust.edu.cn
_publ_contact_author_name        'Yongshu Xie'
loop_
_publ_author_name
'Shangjun Chen'
'Yuheng Yang'
'Yue Wu'
'He Tian'
'Weihong Zhu'

data_pna21
_database_code_depnum_ccdc_archive 'CCDC 835390'
#TrackingRef 'pna21.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H20 N2 O2 S3'
_chemical_formula_weight         512.64

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'
O O 0.0106 0.0060 '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           Orthorhombic
_symmetry_space_group_name_H-M   Pna2(1)

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'

_cell_length_a                   11.241(5)
_cell_length_b                   20.080(8)
_cell_length_c                   10.684(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2411.3(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.17
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1064
_exptl_absorpt_coefficient_mu    0.338
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9325
_exptl_absorpt_correction_T_max  0.9449
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      296(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8007
_diffrn_reflns_av_R_equivalents  0.0280
_diffrn_reflns_av_sigmaI/netI    0.0392
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.03
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3491
_reflns_number_gt                3161
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of 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^)+(0.0428P)^2^+0.2053P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.07(7)
_refine_ls_number_reflns         3491
_refine_ls_number_parameters     318
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0370
_refine_ls_R_factor_gt           0.0315
_refine_ls_wR_factor_ref         0.0811
_refine_ls_wR_factor_gt          0.0770
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.004
_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 0.1713(2) 1.00930(14) 0.2876(3) 0.0473(7) Uani 1 1 d . . .
C2 C 0.0706(3) 0.97580(15) 0.2521(4) 0.0622(9) Uani 1 1 d . . .
H2 H 0.0747 0.9399 0.1974 0.075 Uiso 1 1 calc R . .
C3 C -0.0382(3) 0.99706(19) 0.3003(5) 0.0791(13) Uani 1 1 d . . .
H3 H -0.1055 0.9730 0.2773 0.095 Uiso 1 1 calc R . .
C4 C 0.0453(4) 1.08032(19) 0.4061(4) 0.0756(11) Uani 1 1 d . . .
H4 H 0.0387 1.1172 0.4584 0.091 Uiso 1 1 calc R . .
C5 C 0.1571(3) 1.06274(17) 0.3658(3) 0.0607(9) Uani 1 1 d . . .
H5 H 0.2231 1.0871 0.3917 0.073 Uiso 1 1 calc R . .
C6 C 0.2887(2) 0.98863(13) 0.2403(3) 0.0441(7) Uani 1 1 d . . .
C7 C 0.3199(2) 0.93125(13) 0.1829(3) 0.0421(7) Uani 1 1 d . . .
H7 H 0.2657 0.8979 0.1631 0.050 Uiso 1 1 calc R . .
C8 C 0.4431(2) 0.92672(13) 0.1557(3) 0.0402(6) Uani 1 1 d . . .
C9 C 0.5041(2) 0.98276(13) 0.1893(3) 0.0431(7) Uani 1 1 d . . .
C10 C 0.6330(2) 0.99849(15) 0.1710(4) 0.0606(10) Uani 1 1 d . . .
H10A H 0.6728 0.9978 0.2504 0.091 Uiso 1 1 calc R . .
H10B H 0.6407 1.0419 0.1341 0.091 Uiso 1 1 calc R . .
H10C H 0.6681 0.9659 0.1166 0.091 Uiso 1 1 calc R . .
C11 C 0.9496(2) 0.84650(14) 0.4400(3) 0.0417(7) Uani 1 1 d . . .
C12 C 0.9839(3) 0.87918(18) 0.5474(4) 0.0623(9) Uani 1 1 d . . .
H12 H 0.9277 0.9003 0.5976 0.075 Uiso 1 1 calc R . .
C13 C 1.1023(3) 0.8802(2) 0.5796(4) 0.0748(11) Uani 1 1 d . . .
H13 H 1.1234 0.9031 0.6519 0.090 Uiso 1 1 calc R . .
C14 C 1.1537(3) 0.81927(16) 0.4138(3) 0.0557(8) Uani 1 1 d . . .
H14 H 1.2116 0.7978 0.3666 0.067 Uiso 1 1 calc R . .
C15 C 1.0377(2) 0.81575(14) 0.3733(3) 0.0489(7) Uani 1 1 d . . .
H15 H 1.0192 0.7925 0.3005 0.059 Uiso 1 1 calc R . .
C16 C 0.8260(2) 0.84547(13) 0.3967(3) 0.0393(6) Uani 1 1 d . . .
C17 C 0.7837(2) 0.83793(12) 0.2786(3) 0.0385(6) Uani 1 1 d . . .
H17 H 0.8327 0.8303 0.2099 0.046 Uiso 1 1 calc R . .
C18 C 0.6571(2) 0.84280(12) 0.2691(3) 0.0358(6) Uani 1 1 d . . .
C19 C 0.6057(2) 0.85329(15) 0.3835(3) 0.0421(7) Uani 1 1 d . . .
C20 C 0.4767(3) 0.85657(19) 0.4191(3) 0.0604(9) Uani 1 1 d . . .
H20A H 0.4513 0.9022 0.4203 0.091 Uiso 1 1 calc R . .
H20B H 0.4660 0.8374 0.5006 0.091 Uiso 1 1 calc R . .
H20C H 0.4303 0.8322 0.3590 0.091 Uiso 1 1 calc R . .
C21 C 0.5949(2) 0.83567(13) 0.1507(3) 0.0365(6) Uani 1 1 d . . .
C22 C 0.5002(2) 0.86728(13) 0.1008(3) 0.0375(6) Uani 1 1 d . . .
C23 C 0.4618(3) 0.84023(14) -0.0210(3) 0.0412(7) Uani 1 1 d . . .
C24 C 0.3674(3) 0.86001(15) -0.0952(3) 0.0499(8) Uani 1 1 d . . .
H24 H 0.3169 0.8940 -0.0695 0.060 Uiso 1 1 calc R . .
C25 C 0.3495(3) 0.82805(18) -0.2092(3) 0.0614(9) Uani 1 1 d . . .
H25 H 0.2865 0.8411 -0.2599 0.074 Uiso 1 1 calc R . .
C26 C 0.4227(3) 0.77773(17) -0.2482(3) 0.0653(9) Uani 1 1 d . . .
H26 H 0.4081 0.7571 -0.3246 0.078 Uiso 1 1 calc R . .
C27 C 0.5170(3) 0.75720(16) -0.1771(3) 0.0576(9) Uani 1 1 d . . .
H27 H 0.5676 0.7234 -0.2037 0.069 Uiso 1 1 calc R . .
C28 C 0.5335(3) 0.78890(15) -0.0647(3) 0.0443(7) Uani 1 1 d . . .
N1 N -0.0540(3) 1.04832(17) 0.3755(4) 0.0799(10) Uani 1 1 d . . .
N2 N 1.1880(2) 0.85122(15) 0.5157(3) 0.0673(8) Uani 1 1 d . . .
O1 O 0.76092(19) 0.79267(11) -0.0030(2) 0.0573(5) Uani 1 1 d . . .
O2 O 0.6362(2) 0.70819(10) 0.0972(2) 0.0607(6) Uani 1 1 d . . .
S1 S 0.41149(6) 1.03949(3) 0.25764(10) 0.0518(2) Uani 1 1 d . . .
S2 S 0.71011(7) 0.85831(4) 0.49926(8) 0.0532(2) Uani 1 1 d . . .
S3 S 0.64709(6) 0.77371(3) 0.04470(7) 0.04225(18) 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
C1 0.0429(15) 0.0400(15) 0.059(2) 0.0093(15) -0.0085(16) 0.0080(12)
C2 0.0425(16) 0.0441(17) 0.100(3) 0.007(2) -0.006(2) 0.0059(12)
C3 0.0437(18) 0.061(2) 0.132(4) 0.025(3) -0.002(2) 0.0031(17)
C4 0.077(3) 0.072(2) 0.078(3) -0.003(2) 0.007(2) 0.024(2)
C5 0.0524(19) 0.064(2) 0.066(2) -0.0056(18) -0.0062(18) 0.0157(16)
C6 0.0377(14) 0.0391(14) 0.056(2) 0.0016(14) -0.0111(15) 0.0015(11)
C7 0.0389(14) 0.0362(15) 0.0511(18) 0.0016(13) -0.0095(14) -0.0007(12)
C8 0.0396(15) 0.0371(15) 0.0439(16) 0.0023(13) -0.0105(14) 0.0003(11)
C9 0.0357(13) 0.0354(14) 0.0582(19) 0.0002(13) -0.0096(15) -0.0019(11)
C10 0.0410(15) 0.0460(17) 0.095(3) -0.0106(19) -0.0022(18) -0.0037(13)
C11 0.0396(15) 0.0449(16) 0.0405(15) -0.0001(13) -0.0026(14) -0.0004(12)
C12 0.0500(17) 0.087(2) 0.0499(18) -0.026(2) -0.0122(17) 0.0106(17)
C13 0.057(2) 0.109(3) 0.058(2) -0.033(2) -0.0196(18) 0.012(2)
C14 0.0442(17) 0.061(2) 0.061(2) -0.0129(17) -0.0052(17) 0.0092(15)
C15 0.0405(16) 0.0570(18) 0.0492(18) -0.0142(15) -0.0053(15) 0.0031(14)
C16 0.0347(14) 0.0436(16) 0.0397(16) -0.0057(13) -0.0024(13) 0.0040(12)
C17 0.0339(13) 0.0425(14) 0.0391(15) -0.0035(13) -0.0006(13) 0.0002(11)
C18 0.0330(13) 0.0349(13) 0.0394(15) 0.0017(12) -0.0021(14) 0.0004(10)
C19 0.0349(15) 0.0527(18) 0.0386(16) 0.0005(14) -0.0008(13) 0.0041(13)
C20 0.0406(17) 0.090(3) 0.050(2) 0.0100(18) 0.0051(16) 0.0100(16)
C21 0.0359(14) 0.0352(14) 0.0383(15) 0.0001(12) 0.0021(13) -0.0021(11)
C22 0.0343(14) 0.0393(15) 0.0389(15) 0.0013(13) -0.0042(13) -0.0047(11)
C23 0.0450(15) 0.0409(15) 0.0377(16) 0.0062(12) -0.0029(13) -0.0097(12)
C24 0.0494(18) 0.0505(17) 0.0498(18) 0.0125(15) -0.0144(16) -0.0123(14)
C25 0.067(2) 0.070(2) 0.047(2) 0.0187(17) -0.0243(18) -0.0247(18)
C26 0.090(3) 0.070(2) 0.0364(17) -0.0012(18) -0.013(2) -0.0209(19)
C27 0.077(2) 0.0574(19) 0.0386(17) -0.0047(15) -0.0027(18) -0.0094(17)
C28 0.0529(17) 0.0436(16) 0.0363(15) 0.0046(13) -0.0034(15) -0.0079(14)
N1 0.064(2) 0.069(2) 0.107(3) 0.022(2) 0.015(2) 0.0220(17)
N2 0.0464(15) 0.087(2) 0.068(2) -0.0184(17) -0.0173(16) 0.0094(14)
O1 0.0490(11) 0.0698(13) 0.0532(13) -0.0051(11) 0.0106(11) 0.0051(10)
O2 0.0857(17) 0.0414(12) 0.0550(13) 0.0047(10) -0.0010(13) 0.0121(11)
S1 0.0424(4) 0.0384(4) 0.0746(5) -0.0092(4) -0.0103(4) -0.0006(3)
S2 0.0436(4) 0.0798(6) 0.0362(4) -0.0067(4) -0.0007(4) 0.0116(4)
S3 0.0494(4) 0.0414(4) 0.0360(3) -0.0017(3) 0.0016(4) 0.0043(3)

_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 C5 1.370(4) . ?
C1 C2 1.370(4) . ?
C1 C6 1.472(4) . ?
C2 C3 1.394(5) . ?
C3 N1 1.318(6) . ?
C4 N1 1.329(5) . ?
C4 C5 1.375(5) . ?
C6 C7 1.352(4) . ?
C6 S1 1.727(3) . ?
C7 C8 1.418(4) . ?
C8 C9 1.366(4) . ?
C8 C22 1.476(4) . ?
C9 C10 1.495(4) . ?
C9 S1 1.707(3) . ?
C11 C15 1.367(4) . ?
C11 C12 1.377(4) . ?
C11 C16 1.465(4) . ?
C12 C13 1.374(4) . ?
C13 N2 1.316(4) . ?
C14 N2 1.321(5) . ?
C14 C15 1.376(4) . ?
C16 C17 1.356(4) . ?
C16 S2 1.721(3) . ?
C17 C18 1.430(3) . ?
C18 C19 1.368(4) . ?
C18 C21 1.453(4) . ?
C19 C20 1.500(4) . ?
C19 S2 1.708(3) . ?
C21 C22 1.349(4) . ?
C21 S3 1.782(3) . ?
C22 C23 1.474(4) . ?
C23 C24 1.383(4) . ?
C23 C28 1.389(4) . ?
C24 C25 1.391(5) . ?
C25 C26 1.368(5) . ?
C26 C27 1.368(5) . ?
C27 C28 1.372(4) . ?
C28 S3 1.758(3) . ?
O1 S3 1.429(2) . ?
O2 S3 1.436(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
C5 C1 C2 117.2(3) . . ?
C5 C1 C6 122.3(3) . . ?
C2 C1 C6 120.5(3) . . ?
C1 C2 C3 118.2(4) . . ?
N1 C3 C2 125.6(4) . . ?
N1 C4 C5 124.5(4) . . ?
C1 C5 C4 119.9(4) . . ?
C7 C6 C1 129.0(2) . . ?
C7 C6 S1 110.2(2) . . ?
C1 C6 S1 120.8(2) . . ?
C6 C7 C8 113.7(2) . . ?
C9 C8 C7 112.5(2) . . ?
C9 C8 C22 123.5(2) . . ?
C7 C8 C22 123.9(2) . . ?
C8 C9 C10 128.7(3) . . ?
C8 C9 S1 110.9(2) . . ?
C10 C9 S1 120.4(2) . . ?
C15 C11 C12 116.6(3) . . ?
C15 C11 C16 121.0(3) . . ?
C12 C11 C16 122.4(3) . . ?
C13 C12 C11 119.1(3) . . ?
N2 C13 C12 125.0(3) . . ?
N2 C14 C15 124.2(3) . . ?
C11 C15 C14 119.9(3) . . ?
C17 C16 C11 128.9(3) . . ?
C17 C16 S2 110.1(2) . . ?
C11 C16 S2 121.0(2) . . ?
C16 C17 C18 114.0(3) . . ?
C19 C18 C17 111.6(2) . . ?
C19 C18 C21 126.1(2) . . ?
C17 C18 C21 122.3(2) . . ?
C18 C19 C20 129.9(3) . . ?
C18 C19 S2 111.4(2) . . ?
C20 C19 S2 118.6(2) . . ?
C22 C21 C18 132.7(3) . . ?
C22 C21 S3 109.7(2) . . ?
C18 C21 S3 117.62(19) . . ?
C21 C22 C23 114.0(3) . . ?
C21 C22 C8 124.5(3) . . ?
C23 C22 C8 121.4(2) . . ?
C24 C23 C28 117.7(3) . . ?
C24 C23 C22 128.7(3) . . ?
C28 C23 C22 113.6(2) . . ?
C23 C24 C25 118.7(3) . . ?
C26 C25 C24 121.3(3) . . ?
C27 C26 C25 121.3(3) . . ?
C26 C27 C28 116.8(3) . . ?
C27 C28 C23 124.1(3) . . ?
C27 C28 S3 126.8(3) . . ?
C23 C28 S3 109.1(2) . . ?
C3 N1 C4 114.5(3) . . ?
C13 N2 C14 115.3(3) . . ?
C9 S1 C6 92.69(14) . . ?
C19 S2 C16 92.86(15) . . ?
O1 S3 O2 117.38(14) . . ?
O1 S3 C28 111.55(15) . . ?
O2 S3 C28 110.92(14) . . ?
O1 S3 C21 109.62(13) . . ?
O2 S3 C21 111.31(14) . . ?
C28 S3 C21 93.55(14) . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.033