# Supplementary Material (ESI) for Journal of Materials Chemistry
# This journal is (C) The Royal Society of Chemistry 2007


data_global
_journal_name_full               J.Mater.Chem.

_journal_coden_Cambridge         1145

_publ_contact_author_name        'Yu-Peng Tian'
_publ_contact_author_address     
;
Department of Chemistry
Anhui University
Longhe Road
Hefei
230039
CHINA
;

_publ_contact_author_email       YPTIAN@AHU.EDU.CN

_publ_section_title              
;
Investigations and facile synthesis of a series of
novel multi-functional two-photon materials
;
loop_
_publ_author_name
'Yu-Peng Tian'
'Ya-Hui Guo'
'Wen-Hao Huang'
'Min-Hua Jiang'
'Lin Li'
;
Ping-Ping Sun
;
'Xutang Tao'
'Li-Min Tao'
'Chuan-Kui Wang'
'Jie-Ying Wu'
'Hui Xing'
;
Jia-Xiang Yang
;
'Ju-Zhou Zhang'
'Hongping zhou'

data_tian245
_database_code_depnum_ccdc_archive 'CCDC 648000'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H18 N4'
_chemical_formula_weight         398.45

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'

_symmetry_cell_setting           Rhombohedral
_symmetry_space_group_name_H-M   'R-3 '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   15.244(5)
_cell_length_b                   15.244(5)
_cell_length_c                   16.059(5)
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 90.000(5)
_cell_angle_gamma                120.000(5)
_cell_volume                     3231.8(18)
_cell_formula_units_Z            6
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.23
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1248
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9673
_exptl_absorpt_correction_T_max  0.9831
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71069
_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            7129
_diffrn_reflns_av_R_equivalents  0.0629
_diffrn_reflns_av_sigmaI/netI    0.0709
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.00
_diffrn_reflns_theta_max         28.57
_reflns_number_total             1806
_reflns_number_gt                701
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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^)+(0.0673P)^2^+10.6538P] 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         1806
_refine_ls_number_parameters     94
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1803
_refine_ls_R_factor_gt           0.0757
_refine_ls_wR_factor_ref         0.2335
_refine_ls_wR_factor_gt          0.1830
_refine_ls_goodness_of_fit_ref   0.939
_refine_ls_restrained_S_all      0.939
_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
N1 N 1.0000 1.0000 0.3515(3) 0.0541(12) Uani 1 3 d S . .
C1 C 0.9201(2) 0.8981(2) 0.3601(2) 0.0508(8) Uani 1 1 d . . .
C6 C 0.9301(3) 0.8298(2) 0.4100(2) 0.0566(9) Uani 1 1 d . . .
H6 H 0.9914 0.8488 0.4363 0.068 Uiso 1 1 calc R . .
C5 C 0.8483(3) 0.7326(3) 0.4208(2) 0.0634(10) Uani 1 1 d . . .
H5 H 0.8559 0.6870 0.4541 0.076 Uiso 1 1 calc R . .
C3 C 0.7483(3) 0.7700(3) 0.3328(3) 0.0725(11) Uani 1 1 d . . .
H3 H 0.6870 0.7508 0.3064 0.087 Uiso 1 1 calc R . .
C2 C 0.8284(3) 0.8657(3) 0.3198(2) 0.0655(10) Uani 1 1 d . . .
H2 H 0.8211 0.9093 0.2836 0.079 Uiso 1 1 calc R . .
C4 C 0.7558(3) 0.7022(3) 0.3833(2) 0.0651(10) Uani 1 1 d . . .
C7 C 0.6636(3) 0.6016(3) 0.3988(3) 0.0848(13) Uani 1 1 d . . .
H7 H 0.6026 0.5924 0.3782 0.102 Uiso 1 1 calc R . .
C8 C 0.6606(4) 0.5292(3) 0.4367(3) 0.0922(14) Uani 1 1 d . . .
H8 H 0.7216 0.5348 0.4535 0.111 Uiso 1 1 calc R . .
C9 C 0.5674(4) 0.4358(4) 0.4565(3) 0.0972(15) Uani 1 1 d . . .
N2 N 0.4961(3) 0.3616(3) 0.4757(3) 0.1148(15) 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
N1 0.0462(16) 0.0462(16) 0.070(3) 0.000 0.000 0.0231(8)
C1 0.0482(19) 0.0459(18) 0.0567(19) -0.0051(15) 0.0008(15) 0.0223(15)
C6 0.061(2) 0.054(2) 0.059(2) -0.0034(16) -0.0038(16) 0.0317(18)
C5 0.081(3) 0.049(2) 0.064(2) 0.0015(17) 0.002(2) 0.036(2)
C3 0.057(2) 0.061(2) 0.085(3) -0.003(2) -0.012(2) 0.0183(19)
C2 0.058(2) 0.057(2) 0.075(2) 0.0018(18) -0.0099(18) 0.0236(18)
C4 0.060(2) 0.049(2) 0.072(2) -0.0101(18) -0.0022(19) 0.0165(18)
C7 0.089(3) 0.069(3) 0.090(3) -0.008(2) -0.014(2) 0.034(2)
C8 0.099(3) 0.071(3) 0.099(3) 0.002(3) 0.003(3) 0.036(3)
C9 0.103(4) 0.063(3) 0.103(4) 0.000(3) 0.003(3) 0.024(3)
N2 0.102(3) 0.066(2) 0.143(4) 0.010(3) -0.003(3) 0.018(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
N1 C1 1.423(3) 2_765 ?
N1 C1 1.423(3) . ?
N1 C1 1.423(3) 3_675 ?
C1 C6 1.381(4) . ?
C1 C2 1.389(4) . ?
C6 C5 1.390(5) . ?
C5 C4 1.383(5) . ?
C3 C4 1.362(5) . ?
C3 C2 1.372(5) . ?
C4 C7 1.494(5) . ?
C7 C8 1.241(5) . ?
C8 C9 1.458(6) . ?
C9 N2 1.151(5) . ?

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
C1 N1 C1 119.07(8) 2_765 . ?
C1 N1 C1 119.07(8) 2_765 3_675 ?
C1 N1 C1 119.07(8) . 3_675 ?
C6 C1 C2 118.3(3) . . ?
C6 C1 N1 121.5(3) . . ?
C2 C1 N1 120.2(3) . . ?
C5 C6 C1 119.8(3) . . ?
C6 C5 C4 121.6(3) . . ?
C4 C3 C2 122.1(4) . . ?
C3 C2 C1 120.6(3) . . ?
C3 C4 C5 117.6(3) . . ?
C3 C4 C7 119.1(4) . . ?
C5 C4 C7 123.3(4) . . ?
C8 C7 C4 126.3(5) . . ?
C7 C8 C9 124.0(5) . . ?
N2 C9 C8 176.5(6) . . ?

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
C1 N1 C1 C6 29.0(6) 2_765 . . . ?
C1 N1 C1 C6 -131.9(3) 3_675 . . . ?
C1 N1 C1 C2 -152.8(3) 2_765 . . . ?
C1 N1 C1 C2 46.4(6) 3_675 . . . ?
C2 C1 C6 C5 -2.1(5) . . . . ?
N1 C1 C6 C5 176.1(3) . . . . ?
C1 C6 C5 C4 -0.6(5) . . . . ?
C4 C3 C2 C1 -2.0(6) . . . . ?
C6 C1 C2 C3 3.4(5) . . . . ?
N1 C1 C2 C3 -174.9(3) . . . . ?
C2 C3 C4 C5 -0.8(6) . . . . ?
C2 C3 C4 C7 176.1(4) . . . . ?
C6 C5 C4 C3 2.0(5) . . . . ?
C6 C5 C4 C7 -174.7(3) . . . . ?
C3 C4 C7 C8 172.9(5) . . . . ?
C5 C4 C7 C8 -10.4(7) . . . . ?
C4 C7 C8 C9 174.4(4) . . . . ?
C7 C8 C9 N2 -149(9) . . . . ?

_diffrn_measured_fraction_theta_max 0.980
_diffrn_reflns_theta_full        28.57
_diffrn_measured_fraction_theta_full 0.980
_refine_diff_density_max         0.449
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.050