# Supplementary Material (ESI) for Journal of Materials Chemistry
# This journal is © The Royal Society of Chemistry 2005

data_global
_journal_name_full               J.Mater.Chem.

_journal_coden_Cambridge         1145

_publ_contact_author_name        "Jiann T'suen Lin"
_publ_contact_author_address     
;
Institute of Chemistry
Academia Sinica
No. 128, Sec. 2, Yang-Chiu-Yan Rd.,
Taipei
115
TAIWAN
;

_publ_contact_author_email       JTLIN@CHEM.SINICA.EDU.TW

_publ_section_title              
;
Synthesis and Characterization of New Fluorescent
Two-Photon Absorption Chromophores
;
loop_
_publ_author_name
"Jiann T'suen Lin"
'Pi-Tai Chou.'
'Ping-Hsin Huang.'
'Shin-Chien Pu.'
;
Jiun Yi Shen
;
'Yuh-Sheng Wen.'
'Yeh.Ming-Chang P'

# Attachment 'Cpd.12.cif'

data_i6989
_database_code_depnum_ccdc_archive 'CCDC 282997'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C52 H36 Cl4 N4 O S2'
_chemical_formula_sum            'C52 H36 Cl4 N4 O S2'
_chemical_formula_weight         938.77

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Cl Cl 0.1484 0.1585 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2

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

_cell_length_a                   9.9509(2)
_cell_length_b                   25.1959(5)
_cell_length_c                   9.0316(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2264.42(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    100.0(1)
_cell_measurement_reflns_used    5468
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      26.35

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             968
_exptl_absorpt_coefficient_mu    0.398
_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      100.0(1)
_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            19843
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_av_sigmaI/netI    0.0355
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.62
_diffrn_reflns_theta_max         25.03
_reflns_number_total             3991
_reflns_number_gt                3528
_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, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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^)+(0.0684P)^2^+1.9570P] 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    mixed
_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   0.01(1)
_refine_ls_number_reflns         3991
_refine_ls_number_parameters     285
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0551
_refine_ls_R_factor_gt           0.0464
_refine_ls_wR_factor_ref         0.1349
_refine_ls_wR_factor_gt          0.1286
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_restrained_S_all      1.110
_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
Cl1 Cl 0.64788(15) 0.94081(6) 0.70872(15) 0.0627(4) Uani 1 1 d . . .
Cl2 Cl 0.92743(14) 0.92224(6) 0.79567(16) 0.0617(4) Uani 1 1 d . . .
S1 S 0.64932(9) 0.55583(4) 0.86038(10) 0.0235(2) Uani 1 1 d . . .
O1 O 1.0000 0.5000 0.7169(4) 0.0210(8) Uani 1 2 d S . .
N3 N 0.9343(3) 0.50930(13) 0.9485(4) 0.0283(7) Uani 1 1 d . . .
N30 N -0.1971(3) 0.68430(11) 0.9359(3) 0.0186(6) Uani 1 1 d . . .
C1 C 0.7820(5) 0.9629(2) 0.8209(6) 0.0547(14) Uani 1 1 d . . .
H1A H 0.7544 0.9619 0.9262 0.066 Uiso 1 1 calc R . .
H1B H 0.8042 1.0001 0.7953 0.066 Uiso 1 1 calc R . .
C2 C 0.9011(4) 0.51390(13) 0.8109(4) 0.0225(8) Uani 1 1 d . . .
C12 C 0.7739(3) 0.53151(13) 0.7481(4) 0.0204(8) Uani 1 1 d . . .
C13 C 0.7381(4) 0.53055(14) 0.6037(4) 0.0231(8) Uani 1 1 d . . .
H13 H 0.7948 0.5180 0.5268 0.028 Uiso 1 1 calc R . .
C14 C 0.6072(3) 0.55029(14) 0.5800(4) 0.0228(8) Uani 1 1 d . . .
H14 H 0.5665 0.5527 0.4851 0.027 Uiso 1 1 calc R . .
C15 C 0.5450(3) 0.56555(13) 0.7084(4) 0.0222(8) Uani 1 1 d . . .
C16 C 0.4162(4) 0.58671(14) 0.7305(4) 0.0229(8) Uani 1 1 d . . .
C17 C 0.3061(3) 0.60516(14) 0.7540(4) 0.0222(8) Uani 1 1 d . . .
C21 C 0.1801(3) 0.62652(13) 0.7949(4) 0.0194(7) Uani 1 1 d . . .
C22 C 0.0711(3) 0.63070(13) 0.6954(4) 0.0212(8) Uani 1 1 d . . .
H22 H 0.0825 0.6200 0.5953 0.025 Uiso 1 1 calc R . .
C23 C -0.0507(3) 0.64994(13) 0.7406(4) 0.0186(7) Uani 1 1 d . . .
H23 H -0.1227 0.6526 0.6719 0.022 Uiso 1 1 calc R . .
C24 C -0.0699(3) 0.66594(13) 0.8893(4) 0.0171(7) Uani 1 1 d . . .
C25 C 0.0377(3) 0.66345(13) 0.9861(4) 0.0184(7) Uani 1 1 d . . .
H25 H 0.0270 0.6756 1.0849 0.022 Uiso 1 1 calc R . .
C26 C 0.1591(4) 0.64375(13) 0.9419(4) 0.0207(8) Uani 1 1 d . . .
H26 H 0.2306 0.6416 1.0113 0.025 Uiso 1 1 calc R . .
C31 C -0.2795(3) 0.71424(13) 0.8377(4) 0.0190(8) Uani 1 1 d . . .
C32 C -0.2270(4) 0.75627(14) 0.7569(4) 0.0237(8) Uani 1 1 d . . .
H32 H -0.1351 0.7656 0.7677 0.028 Uiso 1 1 calc R . .
C33 C -0.3075(4) 0.78440(15) 0.6613(4) 0.0286(9) Uani 1 1 d . . .
H33 H -0.2703 0.8128 0.6054 0.034 Uiso 1 1 calc R . .
C34 C -0.4422(4) 0.77181(16) 0.6457(4) 0.0283(9) Uani 1 1 d . . .
H34 H -0.4975 0.7914 0.5797 0.034 Uiso 1 1 calc R . .
C35 C -0.4956(4) 0.73013(15) 0.7279(4) 0.0267(9) Uani 1 1 d . . .
H35 H -0.5880 0.7214 0.7184 0.032 Uiso 1 1 calc R . .
C36 C -0.4154(3) 0.70137(14) 0.8231(4) 0.0209(8) Uani 1 1 d . . .
H36 H -0.4524 0.6729 0.8786 0.025 Uiso 1 1 calc R . .
C41 C -0.2380(3) 0.67691(14) 1.0859(4) 0.0180(7) Uani 1 1 d . . .
C42 C -0.3127(3) 0.71542(14) 1.1573(4) 0.0205(8) Uani 1 1 d . . .
H42 H -0.3390 0.7465 1.1054 0.025 Uiso 1 1 calc R . .
C43 C -0.3493(4) 0.70881(15) 1.3045(4) 0.0259(8) Uani 1 1 d . . .
H43 H -0.4013 0.7353 1.3525 0.031 Uiso 1 1 calc R . .
C44 C -0.3109(4) 0.66416(16) 1.3813(4) 0.0280(9) Uani 1 1 d . . .
H44 H -0.3335 0.6602 1.4829 0.034 Uiso 1 1 calc R . .
C45 C -0.2389(4) 0.62517(16) 1.3085(4) 0.0277(9) Uani 1 1 d . . .
H45 H -0.2139 0.5939 1.3604 0.033 Uiso 1 1 calc R . .
C46 C -0.2027(3) 0.63073(14) 1.1621(4) 0.0211(8) Uani 1 1 d . . .
H46 H -0.1540 0.6034 1.1134 0.025 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
Cl1 0.0680(9) 0.0670(8) 0.0533(8) 0.0058(7) -0.0032(7) -0.0034(7)
Cl2 0.0549(8) 0.0680(8) 0.0621(8) 0.0019(7) 0.0221(7) 0.0062(7)
S1 0.0177(4) 0.0244(5) 0.0285(5) -0.0038(4) 0.0014(4) 0.0041(4)
O1 0.0145(16) 0.0190(17) 0.029(2) 0.000 0.000 0.0055(14)
N3 0.0191(15) 0.0335(18) 0.0322(19) -0.0001(15) 0.0003(14) 0.0078(14)
N30 0.0158(14) 0.0229(15) 0.0172(15) 0.0041(12) 0.0033(12) 0.0030(12)
C1 0.051(3) 0.057(3) 0.056(3) -0.007(3) 0.007(3) 0.000(3)
C2 0.0186(17) 0.0151(17) 0.034(2) 0.0015(16) 0.0054(16) -0.0004(15)
C12 0.0138(16) 0.0160(16) 0.031(2) 0.0004(15) 0.0054(16) 0.0019(14)
C13 0.0190(18) 0.0213(18) 0.029(2) 0.0015(15) 0.0069(16) 0.0025(15)
C14 0.0206(18) 0.0232(19) 0.0245(19) 0.0018(15) 0.0007(15) 0.0033(16)
C15 0.0148(16) 0.0179(18) 0.034(2) 0.0034(16) -0.0008(15) 0.0000(14)
C16 0.0216(19) 0.0204(17) 0.027(2) 0.0001(15) 0.0014(16) -0.0017(15)
C17 0.0188(19) 0.0195(17) 0.028(2) -0.0011(16) -0.0003(16) -0.0011(15)
C21 0.0139(17) 0.0158(16) 0.0285(19) 0.0012(15) -0.0001(15) 0.0000(13)
C22 0.0216(18) 0.0194(17) 0.0224(18) 0.0009(15) 0.0015(16) -0.0023(15)
C23 0.0166(17) 0.0181(16) 0.0213(18) 0.0014(14) -0.0020(15) 0.0010(14)
C24 0.0155(16) 0.0143(16) 0.0214(18) 0.0011(14) 0.0033(14) 0.0012(14)
C25 0.0205(18) 0.0168(17) 0.0180(17) 0.0007(14) -0.0009(14) 0.0000(15)
C26 0.0170(17) 0.0181(17) 0.0270(19) 0.0024(15) -0.0055(16) 0.0012(15)
C31 0.0179(16) 0.0209(17) 0.0182(18) -0.0019(14) -0.0009(15) 0.0043(14)
C32 0.0214(18) 0.0267(19) 0.023(2) 0.0028(16) 0.0052(15) 0.0039(16)
C33 0.039(2) 0.0237(19) 0.023(2) 0.0041(16) 0.0089(17) 0.0060(17)
C34 0.037(2) 0.032(2) 0.0158(19) -0.0020(16) -0.0036(17) 0.0205(18)
C35 0.0223(18) 0.032(2) 0.026(2) -0.0117(18) -0.0056(17) 0.0085(16)
C36 0.0216(17) 0.0209(18) 0.0204(18) -0.0043(15) 0.0008(15) 0.0013(15)
C41 0.0137(16) 0.0228(18) 0.0176(17) 0.0006(14) -0.0028(14) -0.0029(14)
C42 0.0164(17) 0.0252(18) 0.0201(19) 0.0014(15) -0.0009(14) 0.0015(15)
C43 0.0203(17) 0.034(2) 0.0231(19) -0.0056(16) -0.0037(17) 0.0002(17)
C44 0.0225(19) 0.043(2) 0.0181(18) -0.0002(17) 0.0003(15) -0.0020(17)
C45 0.0238(19) 0.034(2) 0.025(2) 0.0097(17) 0.0010(17) 0.0016(17)
C46 0.0181(17) 0.0210(18) 0.024(2) -0.0002(15) -0.0004(15) 0.0011(14)

_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
Cl1 C1 1.766(6) . ?
Cl2 C1 1.788(5) . ?
S1 C12 1.714(4) . ?
S1 C15 1.739(4) . ?
O1 C2 1.346(4) 2_765 ?
O1 C2 1.346(4) . ?
N3 C2 1.291(5) . ?
N3 N3 1.389(6) 2_765 ?
N30 C24 1.412(4) . ?
N30 C31 1.424(4) . ?
N30 C41 1.427(4) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C12 1.457(5) . ?
C12 C13 1.352(6) . ?
C13 C14 1.411(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.369(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.402(5) . ?
C16 C17 1.209(5) . ?
C17 C21 1.413(5) . ?
C21 C22 1.413(5) . ?
C21 C26 1.413(5) . ?
C22 C23 1.368(5) . ?
C22 H22 0.9500 . ?
C23 C24 1.415(5) . ?
C23 H23 0.9500 . ?
C24 C25 1.384(5) . ?
C25 C26 1.365(5) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C31 C32 1.388(5) . ?
C31 C36 1.396(5) . ?
C32 C33 1.374(5) . ?
C32 H32 0.9500 . ?
C33 C34 1.384(6) . ?
C33 H33 0.9500 . ?
C34 C35 1.392(6) . ?
C34 H34 0.9500 . ?
C35 C36 1.379(5) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
C41 C42 1.381(5) . ?
C41 C46 1.397(5) . ?
C42 C43 1.389(5) . ?
C42 H42 0.9500 . ?
C43 C44 1.376(5) . ?
C43 H43 0.9500 . ?
C44 C45 1.383(6) . ?
C44 H44 0.9500 . ?
C45 C46 1.377(5) . ?
C45 H45 0.9500 . ?
C46 H46 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 S1 C15 90.87(18) . . ?
C2 O1 C2 101.8(4) 2_765 . ?
C2 N3 N3 105.7(2) . 2_765 ?
C24 N30 C31 120.3(3) . . ?
C24 N30 C41 119.8(3) . . ?
C31 N30 C41 119.7(3) . . ?
Cl1 C1 Cl2 111.0(3) . . ?
Cl1 C1 H1A 109.4 . . ?
Cl2 C1 H1A 109.4 . . ?
Cl1 C1 H1B 109.4 . . ?
Cl2 C1 H1B 109.4 . . ?
H1A C1 H1B 108.0 . . ?
N3 C2 O1 113.4(3) . . ?
N3 C2 C12 128.6(3) . . ?
O1 C2 C12 118.0(3) . . ?
C13 C12 C2 126.8(3) . . ?
C13 C12 S1 112.7(3) . . ?
C2 C12 S1 120.5(3) . . ?
C12 C13 C14 112.5(3) . . ?
C12 C13 H13 123.7 . . ?
C14 C13 H13 123.7 . . ?
C15 C14 C13 112.8(3) . . ?
C15 C14 H14 123.6 . . ?
C13 C14 H14 123.6 . . ?
C14 C15 C16 129.9(4) . . ?
C14 C15 S1 111.0(3) . . ?
C16 C15 S1 119.1(3) . . ?
C17 C16 C15 178.1(4) . . ?
C16 C17 C21 174.9(4) . . ?
C17 C21 C22 122.9(3) . . ?
C17 C21 C26 119.6(3) . . ?
C22 C21 C26 117.4(3) . . ?
C23 C22 C21 121.1(3) . . ?
C23 C22 H22 119.4 . . ?
C21 C22 H22 119.4 . . ?
C22 C23 C24 120.3(3) . . ?
C22 C23 H23 119.9 . . ?
C24 C23 H23 119.9 . . ?
C25 C24 N30 121.3(3) . . ?
C25 C24 C23 118.8(3) . . ?
N30 C24 C23 119.8(3) . . ?
C26 C25 C24 121.1(3) . . ?
C26 C25 H25 119.5 . . ?
C24 C25 H25 119.5 . . ?
C25 C26 C21 121.2(3) . . ?
C25 C26 H26 119.4 . . ?
C21 C26 H26 119.4 . . ?
C32 C31 C36 119.5(3) . . ?
C32 C31 N30 121.0(3) . . ?
C36 C31 N30 119.6(3) . . ?
C33 C32 C31 120.3(4) . . ?
C33 C32 H32 119.8 . . ?
C31 C32 H32 119.8 . . ?
C32 C33 C34 120.7(4) . . ?
C32 C33 H33 119.7 . . ?
C34 C33 H33 119.7 . . ?
C33 C34 C35 119.2(3) . . ?
C33 C34 H34 120.4 . . ?
C35 C34 H34 120.4 . . ?
C36 C35 C34 120.5(4) . . ?
C36 C35 H35 119.7 . . ?
C34 C35 H35 119.7 . . ?
C35 C36 C31 119.8(4) . . ?
C35 C36 H36 120.1 . . ?
C31 C36 H36 120.1 . . ?
C42 C41 C46 119.4(3) . . ?
C42 C41 N30 120.3(3) . . ?
C46 C41 N30 120.3(3) . . ?
C41 C42 C43 120.2(3) . . ?
C41 C42 H42 119.9 . . ?
C43 C42 H42 119.9 . . ?
C44 C43 C42 120.6(4) . . ?
C44 C43 H43 119.7 . . ?
C42 C43 H43 119.7 . . ?
C43 C44 C45 119.0(4) . . ?
C43 C44 H44 120.5 . . ?
C45 C44 H44 120.5 . . ?
C46 C45 C44 121.3(4) . . ?
C46 C45 H45 119.3 . . ?
C44 C45 H45 119.3 . . ?
C45 C46 C41 119.4(3) . . ?
C45 C46 H46 120.3 . . ?
C41 C46 H46 120.3 . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.318
_refine_diff_density_min         -0.592
_refine_diff_density_rms         0.068