# Supplementary Material (ESI) for Chemical Communications
# This journal is (c) The Royal Society of Chemistry 2006

data_publication_text
_journal_name_full               Chem.Commun.
_journal_coden_Cambridge         0182
_publ_contact_author_name        'Yuguang Ma'
_publ_contact_author_address     
;Key Lab for Supramolecular Structure
and Materials of Ministry of Education, College of Chemistry,
Jilin University, Changchun 130012, P. R. China
;
_publ_contact_author_email       ygma@jlu.edu.cn
_publ_contact_author_phone       '86 431 5168480'
_publ_contact_author_fax         '86 431 5168480'
loop_
_publ_author_name
_publ_author_address
'Yupeng Li.'
;Key Lab for Supramolecular Structure
and Materials of Ministry of Education, College of Chemistry,
Jilin University, Changchun 130012, P. R. China
;
'Feng Li.'
;Key Lab for Supramolecular Structure
and Materials of Ministry of Education, College of Chemistry,
Jilin University, Changchun 130012, P. R. China
;
'Houyu Zhang.'
;Key Lab for Supramolecular Structure
and Materials of Ministry of Education, College of Chemistry,
Jilin University, Changchun 130012, P. R. China
;
'Zengqi Xie.'
;Key Lab for Supramolecular Structure
and Materials of Ministry of Education, College of Chemistry,
Jilin University, Changchun 130012, P. R. China
;
'Weijie Xie.'
;Key Lab for Supramolecular Structure
and Materials of Ministry of Education, College of Chemistry,
Jilin University, Changchun 130012, P. R. China
;
'Hai Xu.'
;Key Lab for Supramolecular Structure
and Materials of Ministry of Education, College of Chemistry,
Jilin University, Changchun 130012, P. R. China
;
;
Bao Li
;
;Key Lab for Supramolecular Structure
and Materials of Ministry of Education, College of Chemistry,
Jilin University, Changchun 130012, P. R. China
;
'Fangzhong Shen.'
;Key Lab for Supramolecular Structure
and Materials of Ministry of Education, College of Chemistry,
Jilin University, Changchun 130012, P. R. China
;
'Ling Ye.'
;Key Lab for Supramolecular Structure
and Materials of Ministry of Education, College of Chemistry,
Jilin University, Changchun 130012, P. R. China
;
'Muddasir Hanif'
;Key Lab for Supramolecular Structure
and Materials of Ministry of Education, College of Chemistry,
Jilin University, Changchun 130012, P. R. China.
;
'Dongge Ma.'
;State Key Laboratory of Polymer Physics
and Chemistry, Changchun Institute of Applied Chemistry,
Chinese Academy of Sciences, Changchun 130022, P.R. China.
;
'Yuguang Ma.'
;Key Lab for Supramolecular Structure
and Materials of Ministry of Education, College of Chemistry,
Jilin University, Changchun 130012, P. R. China
;

data_lyp4
_database_code_depnum_ccdc_archive 'CCDC 616163'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C36 H24 N2'
_chemical_formula_weight         484.57

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           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                   6.6450(13)
_cell_length_b                   27.561(6)
_cell_length_c                   7.6528(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 110.83(3)
_cell_angle_gamma                90.00
_cell_volume                     1309.9(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       platelet
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.452
_exptl_crystal_size_mid          0.165
_exptl_crystal_size_min          0.067
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.229
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             508
_exptl_absorpt_coefficient_mu    0.071
_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  ?
_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            12667
_diffrn_reflns_av_R_equivalents  0.0995
_diffrn_reflns_av_sigmaI/netI    0.0880
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.21
_diffrn_reflns_theta_max         27.48
_reflns_number_total             3004
_reflns_number_gt                1259
_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^)+(0.0490P)^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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3004
_refine_ls_number_parameters     220
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1663
_refine_ls_R_factor_gt           0.0591
_refine_ls_wR_factor_ref         0.1399
_refine_ls_wR_factor_gt          0.1057
_refine_ls_goodness_of_fit_ref   0.951
_refine_ls_restrained_S_all      0.951
_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
N N 1.3822(4) 0.11807(9) -0.1317(5) 0.1093(10) Uani 1 1 d . . .
C1 C 1.0517(4) 0.02522(9) -0.1325(3) 0.0503(6) Uani 1 1 d . . .
C2 C 0.9601(4) 0.05032(8) -0.0209(3) 0.0485(6) Uani 1 1 d . . .
C3 C 0.9063(3) 0.02392(8) 0.1142(3) 0.0489(6) Uani 1 1 d . . .
C4 C 0.9098(4) 0.10212(8) -0.0483(3) 0.0491(6) Uani 1 1 d . . .
C5 C 1.0227(4) 0.13718(8) -0.0921(3) 0.0499(6) Uani 1 1 d . . .
C6 C 0.9574(4) 0.18880(8) -0.1216(3) 0.0517(6) Uani 1 1 d . . .
C7 C 0.7730(5) 0.20559(10) -0.0974(4) 0.0757(9) Uani 1 1 d . . .
C8 C 0.7181(6) 0.25388(11) -0.1207(5) 0.0861(10) Uani 1 1 d . . .
C9 C 0.8435(6) 0.28630(12) -0.1679(4) 0.0814(9) Uani 1 1 d . . .
C10 C 1.0244(6) 0.27038(11) -0.1945(5) 0.0873(10) Uani 1 1 d . . .
C11 C 1.0820(5) 0.22240(10) -0.1708(4) 0.0729(8) Uani 1 1 d . . .
C12 C 0.8053(4) 0.04752(8) 0.2371(3) 0.0511(6) Uani 1 1 d . . .
C13 C 0.6232(4) 0.02745(11) 0.2562(4) 0.0638(7) Uani 1 1 d . . .
C14 C 0.5238(6) 0.04988(15) 0.3667(4) 0.0821(10) Uani 1 1 d . . .
C15 C 0.6078(6) 0.09212(14) 0.4597(5) 0.0869(11) Uani 1 1 d . . .
C16 C 0.7887(7) 0.11192(12) 0.4438(4) 0.0818(10) Uani 1 1 d . . .
C17 C 0.8881(5) 0.08986(10) 0.3336(4) 0.0639(7) Uani 1 1 d . . .
C18 C 1.2232(5) 0.12551(9) -0.1115(4) 0.0703(8) Uani 1 1 d . . .
H1 H 1.079(4) 0.0433(8) -0.233(3) 0.064(7) Uiso 1 1 d . . .
H4 H 0.771(4) 0.1111(8) -0.034(3) 0.059(7) Uiso 1 1 d . . .
H7 H 0.678(5) 0.1820(11) -0.069(4) 0.107(10) Uiso 1 1 d . . .
H8 H 0.584(5) 0.2641(11) -0.105(4) 0.106(11) Uiso 1 1 d . . .
H9 H 0.816(5) 0.3208(12) -0.180(4) 0.100(10) Uiso 1 1 d . . .
H10 H 1.120(5) 0.2929(10) -0.233(4) 0.098(10) Uiso 1 1 d . . .
H11 H 1.211(5) 0.2103(10) -0.190(4) 0.089(9) Uiso 1 1 d . . .
H13 H 0.576(4) -0.0026(10) 0.197(3) 0.077(9) Uiso 1 1 d . . .
H14 H 0.397(4) 0.0348(9) 0.374(3) 0.074(8) Uiso 1 1 d . . .
H15 H 0.531(5) 0.1082(10) 0.538(4) 0.102(10) Uiso 1 1 d . . .
H16 H 0.854(5) 0.1419(11) 0.505(4) 0.093(10) Uiso 1 1 d . . .
H17 H 1.023(4) 0.1045(8) 0.326(3) 0.061(7) Uiso 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
N 0.0741(18) 0.0742(18) 0.201(3) 0.0112(19) 0.075(2) -0.0005(14)
C1 0.0565(15) 0.0455(14) 0.0542(14) 0.0044(12) 0.0263(13) -0.0003(11)
C2 0.0482(14) 0.0446(13) 0.0548(14) 0.0031(11) 0.0210(12) -0.0008(11)
C3 0.0507(14) 0.0456(14) 0.0531(13) 0.0009(11) 0.0219(12) -0.0004(11)
C4 0.0522(15) 0.0424(13) 0.0546(15) 0.0035(11) 0.0215(13) 0.0018(11)
C5 0.0468(14) 0.0480(14) 0.0544(14) 0.0006(11) 0.0172(12) -0.0017(11)
C6 0.0554(16) 0.0437(14) 0.0531(14) -0.0022(11) 0.0155(12) -0.0043(12)
C7 0.072(2) 0.0452(17) 0.117(3) 0.0024(16) 0.042(2) -0.0002(14)
C8 0.083(2) 0.0527(18) 0.125(3) 0.0026(18) 0.040(2) 0.0112(17)
C9 0.102(3) 0.0440(17) 0.091(2) 0.0026(16) 0.026(2) 0.0015(18)
C10 0.105(3) 0.0540(19) 0.109(3) 0.0160(17) 0.045(2) -0.0050(18)
C11 0.080(2) 0.0527(17) 0.094(2) 0.0078(15) 0.0412(19) -0.0034(15)
C12 0.0575(16) 0.0458(14) 0.0519(14) 0.0050(11) 0.0216(13) 0.0083(12)
C13 0.0656(18) 0.068(2) 0.0670(17) 0.0072(15) 0.0348(16) 0.0057(15)
C14 0.078(2) 0.100(3) 0.082(2) 0.024(2) 0.045(2) 0.024(2)
C15 0.113(3) 0.091(3) 0.067(2) 0.0122(19) 0.045(2) 0.044(2)
C16 0.118(3) 0.066(2) 0.0609(19) -0.0044(15) 0.031(2) 0.015(2)
C17 0.080(2) 0.0560(17) 0.0573(16) -0.0009(13) 0.0258(16) 0.0041(15)
C18 0.0568(17) 0.0512(16) 0.106(2) 0.0065(15) 0.0330(17) -0.0030(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
N C18 1.140(3) . ?
C1 C3 1.380(3) 3_755 ?
C1 C2 1.396(3) . ?
C2 C3 1.410(3) . ?
C2 C4 1.464(3) . ?
C3 C1 1.380(3) 3_755 ?
C3 C12 1.485(3) . ?
C4 C5 1.338(3) . ?
C5 C18 1.428(3) . ?
C5 C6 1.481(3) . ?
C6 C11 1.381(3) . ?
C6 C7 1.383(3) . ?
C7 C8 1.375(4) . ?
C8 C9 1.355(4) . ?
C9 C10 1.362(4) . ?
C10 C11 1.371(4) . ?
C12 C13 1.385(3) . ?
C12 C17 1.386(3) . ?
C13 C14 1.390(4) . ?
C14 C15 1.375(5) . ?
C15 C16 1.364(5) . ?
C16 C17 1.383(4) . ?

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
C3 C1 C2 122.7(2) 3_755 . ?
C1 C2 C3 118.2(2) . . ?
C1 C2 C4 121.5(2) . . ?
C3 C2 C4 120.22(19) . . ?
C1 C3 C2 119.07(19) 3_755 . ?
C1 C3 C12 119.09(19) 3_755 . ?
C2 C3 C12 121.8(2) . . ?
C5 C4 C2 128.3(2) . . ?
C4 C5 C18 119.4(2) . . ?
C4 C5 C6 124.9(2) . . ?
C18 C5 C6 115.7(2) . . ?
C11 C6 C7 117.3(2) . . ?
C11 C6 C5 120.9(2) . . ?
C7 C6 C5 121.8(2) . . ?
C8 C7 C6 120.9(3) . . ?
C9 C8 C7 120.9(3) . . ?
C8 C9 C10 119.1(3) . . ?
C9 C10 C11 120.7(3) . . ?
C10 C11 C6 121.1(3) . . ?
C13 C12 C17 118.4(2) . . ?
C13 C12 C3 120.0(2) . . ?
C17 C12 C3 121.5(2) . . ?
C12 C13 C14 120.6(3) . . ?
C15 C14 C13 119.9(3) . . ?
C16 C15 C14 120.0(3) . . ?
C15 C16 C17 120.4(3) . . ?
C16 C17 C12 120.7(3) . . ?
N C18 C5 176.9(3) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.145
_refine_diff_density_min         -0.143
_refine_diff_density_rms         0.036