# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry
# This journal is © The Royal Society of Chemistry 2011


data_global
_journal_name_full               J.Mater.Chem.
_journal_coden_cambridge         1145

_publ_contact_author             
;
Ma,Yuguang
State Key Lab for Supramolecular Structure and Materials
College of Chemistry
Jilin University
Changchun 130012
P. R. China
;
_publ_contact_author_phone       '86 431 85168480'
_publ_contact_author_fax         '86 431 85168480'
_publ_contact_author_email       ygma@jlu.edu.cn
_publ_requested_coeditor_name    ?

#==================================================================
# 2. TITLE AND AUTHOR LIST

_publ_section_title              
;
Supramolecular interaction-induced self-assembly
of conjugated organic molecules into ultra-long microtubes
with Wave Guiding and amplified spontaneous emission
;

loop_
_publ_author_name
_publ_author_address
'Yuanxiang Xu'
; State Key Lab for Supramolecular Structure and Materials
College of Chemistry
Jilin University
Changchun 130012
P. R. China
;
'Yuguang Ma'
; State Key Lab for Supramolecular Structure and Materials
College of Chemistry
Jilin University
Changchun 130012
P. R. China
;
#============================================================
data_p-1
_database_code_depnum_ccdc_archive 'CCDC 815708'
#TrackingRef 'web_deposit_cif_file_0_XuYuanxiang_1299129158.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          'not measured'
_chemical_formula_moiety         'C24 H16 N2'
_chemical_formula_sum            'C24 H16 N2'
_chemical_formula_weight         332.39

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           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.737(2)
_cell_length_b                   8.541(3)
_cell_length_c                   8.965(3)
_cell_angle_alpha                79.742(7)
_cell_angle_beta                 68.025(7)
_cell_angle_gamma                67.714(7)
_cell_volume                     442.2(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1824
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      26.45

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             174
_exptl_absorpt_coefficient_mu    0.074
_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      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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 9.00cm
_diffrn_standards_number         none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        none
_diffrn_reflns_number            2845
_diffrn_reflns_av_R_equivalents  0.0394
_diffrn_reflns_av_sigmaI/netI    0.0797
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.45
_diffrn_reflns_theta_max         26.45
_reflns_number_total             1824
_reflns_number_gt                807
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART Apex II'
_computing_cell_refinement       'Bruker SMART Apex II'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    SHELXP-97
_computing_publication_material  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^)+(0.0625P)^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    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.027(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         1824
_refine_ls_number_parameters     151
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.1464
_refine_ls_R_factor_gt           0.0563
_refine_ls_wR_factor_ref         0.1574
_refine_ls_wR_factor_gt          0.1176
_refine_ls_goodness_of_fit_ref   0.946
_refine_ls_restrained_S_all      0.965
_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 0.1966(5) 1.2298(4) 0.3277(4) 0.1084(12) Uani 1 1 d U . .
C1 C -0.3110(6) 1.3798(4) 0.6427(4) 0.0631(9) Uani 1 1 d . . .
H1 H -0.175(4) 1.408(3) 0.589(3) 0.063(9) Uiso 1 1 d . . .
C2 C -0.4623(6) 1.4482(4) 0.7886(4) 0.0731(10) Uani 1 1 d . . .
H2 H -0.420(5) 1.522(4) 0.834(4) 0.094(10) Uiso 1 1 d . . .
C3 C -0.6619(6) 1.4189(4) 0.8584(4) 0.0749(10) Uani 1 1 d . . .
H3 H -0.778(5) 1.465(4) 0.962(4) 0.088(10) Uiso 1 1 d . . .
C4 C -0.7152(6) 1.3180(5) 0.7861(4) 0.0786(11) Uani 1 1 d . . .
H4 H -0.866(5) 1.295(4) 0.845(3) 0.088(10) Uiso 1 1 d . . .
C5 C -0.5639(5) 1.2482(4) 0.6427(4) 0.0696(10) Uani 1 1 d . . .
H5 H -0.599(5) 1.176(4) 0.590(3) 0.085(10) Uiso 1 1 d . . .
C6 C -0.3602(4) 1.2773(3) 0.5669(3) 0.0497(7) Uani 1 1 d . . .
C7 C -0.1995(4) 1.2047(3) 0.4109(3) 0.0505(8) Uani 1 1 d . . .
C8 C -0.2558(5) 1.1426(4) 0.3105(3) 0.0551(8) Uani 1 1 d . . .
H8 H -0.417(4) 1.149(3) 0.348(3) 0.058(8) Uiso 1 1 d . . .
C9 C -0.1175(4) 1.0693(3) 0.1530(3) 0.0518(8) Uani 1 1 d . . .
C10 C -0.2321(5) 1.0797(4) 0.0475(4) 0.0599(9) Uani 1 1 d . . .
H10 H -0.398(5) 1.136(3) 0.080(3) 0.070(9) Uiso 1 1 d . . .
C11 C -0.1165(5) 1.0124(4) -0.1026(4) 0.0572(8) Uani 1 1 d . . .
H11 H -0.196(5) 1.028(3) -0.179(3) 0.079(9) Uiso 1 1 d . . .
C12 C 0.0218(5) 1.2155(4) 0.3626(4) 0.0669(9) 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 0.0643(18) 0.153(3) 0.122(3) -0.062(2) -0.0120(18) -0.048(2)
C1 0.065(2) 0.072(2) 0.060(2) -0.0108(17) -0.0223(17) -0.0265(18)
C2 0.083(2) 0.076(2) 0.067(2) -0.0190(18) -0.024(2) -0.028(2)
C3 0.080(2) 0.073(2) 0.058(2) -0.0146(18) -0.0118(19) -0.018(2)
C4 0.074(2) 0.089(3) 0.068(2) -0.0182(19) 0.0002(19) -0.039(2)
C5 0.067(2) 0.085(3) 0.059(2) -0.0186(18) -0.0066(17) -0.0363(19)
C6 0.0519(16) 0.0526(18) 0.0495(16) -0.0022(13) -0.0206(13) -0.0196(14)
C7 0.0470(16) 0.0603(19) 0.0505(17) -0.0046(14) -0.0187(14) -0.0217(14)
C8 0.0454(17) 0.067(2) 0.0556(18) -0.0068(15) -0.0156(15) -0.0219(15)
C9 0.0477(17) 0.063(2) 0.0488(17) -0.0078(14) -0.0160(14) -0.0216(15)
C10 0.0431(17) 0.080(2) 0.0604(19) -0.0181(16) -0.0193(15) -0.0164(16)
C11 0.0498(17) 0.070(2) 0.0574(19) -0.0125(15) -0.0245(15) -0.0156(15)
C12 0.0552(18) 0.086(2) 0.067(2) -0.0268(17) -0.0156(16) -0.0255(18)

_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 C12 1.148(3) . ?
C1 C2 1.383(4) . ?
C1 C6 1.392(4) . ?
C1 H1 0.96(3) . ?
C2 C3 1.353(4) . ?
C2 H2 0.98(3) . ?
C3 C4 1.379(4) . ?
C3 H3 0.99(3) . ?
C4 C5 1.371(4) . ?
C4 H4 1.03(3) . ?
C5 C6 1.381(4) . ?
C5 H5 0.98(3) . ?
C6 C7 1.476(3) . ?
C7 C8 1.347(3) . ?
C7 C12 1.423(4) . ?
C8 C9 1.464(4) . ?
C8 H8 0.99(2) . ?
C9 C11 1.386(4) 2_575 ?
C9 C10 1.400(4) . ?
C10 C11 1.378(4) . ?
C10 H10 0.98(3) . ?
C11 C9 1.386(4) 2_575 ?
C11 H11 0.98(3) . ?

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 C6 120.4(3) . . ?
C2 C1 H1 120.5(15) . . ?
C6 C1 H1 119.0(15) . . ?
C3 C2 C1 120.6(3) . . ?
C3 C2 H2 122.8(18) . . ?
C1 C2 H2 116.6(18) . . ?
C2 C3 C4 120.3(3) . . ?
C2 C3 H3 124.5(17) . . ?
C4 C3 H3 115.2(17) . . ?
C5 C4 C3 119.2(3) . . ?
C5 C4 H4 122.7(16) . . ?
C3 C4 H4 118.1(16) . . ?
C4 C5 C6 122.1(3) . . ?
C4 C5 H5 120.3(17) . . ?
C6 C5 H5 117.6(17) . . ?
C5 C6 C1 117.5(3) . . ?
C5 C6 C7 122.0(2) . . ?
C1 C6 C7 120.5(3) . . ?
C8 C7 C12 119.8(2) . . ?
C8 C7 C6 124.1(2) . . ?
C12 C7 C6 116.0(2) . . ?
C7 C8 C9 130.2(3) . . ?
C7 C8 H8 114.9(14) . . ?
C9 C8 H8 114.9(14) . . ?
C11 C9 C10 118.0(2) 2_575 . ?
C11 C9 C8 124.8(3) 2_575 . ?
C10 C9 C8 117.2(3) . . ?
C11 C10 C9 121.3(3) . . ?
C11 C10 H10 119.0(15) . . ?
C9 C10 H10 119.6(15) . . ?
C10 C11 C9 120.7(3) . 2_575 ?
C10 C11 H11 120.8(16) . . ?
C9 C11 H11 118.4(16) 2_575 . ?
N1 C12 C7 177.2(3) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        26.45
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.140
_refine_diff_density_rms         0.036