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


data_global
_journal_name_full               Chem.Commun.
_journal_coden_cambridge         0182
#TrackingRef '9490_web_deposit_cif_file_0_ToruOkawara_1328787363.865212.cif'

_audit_creation_method           'APEX2 v2010.1-2'

_publ_contact_author_name        'Toru Okawara'
_publ_contact_author_address     
;
;
_publ_contact_author_email       t-okawara@ms.hisaeda.cstm.kyushu-u.ac.jp
_publ_contact_author_fax         ?
_publ_contact_author_phone       ?

_publ_section_title              
;
;
_publ_section_abstract           
;
;
_publ_section_references         
;
;
_publ_section_comment            
;
;
loop_
_publ_author_name
'Toru Okawara'
'Koichi Hashimoto'
'Masaaki Abe'
'Hisashi Shimakoshi'
'Yoshio Hisaeda'

data_I
_database_code_depnum_ccdc_archive 'CCDC 865212'
#TrackingRef '9490_web_deposit_cif_file_0_ToruOkawara_1328787363.865212.cif'

_audit_creation_method           'APEX2 v2010.1-2'

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H22 N4'
_chemical_formula_iupac          ?
_chemical_formula_weight         462.54

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.799(2)
_cell_length_b                   8.080(3)
_cell_length_c                   12.822(4)
_cell_angle_alpha                104.488(4)
_cell_angle_beta                 92.528(5)
_cell_angle_gamma                96.782(5)
_cell_volume                     675.2(4)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    3110
_cell_measurement_theta_min      2.6271
_cell_measurement_theta_max      29.9946
_cell_measurement_temperature    17

_exptl_crystal_description       prism
_exptl_crystal_colour            violet
_exptl_crystal_size_max          0.68
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.09
_exptl_crystal_density_diffrn    1.138
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             242

_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_correction_T_min  0.69
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      173

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            8859
_diffrn_reflns_av_R_equivalents  0.0445
_diffrn_reflns_av_sigmaI/netI    0.0490
_diffrn_reflns_theta_min         1.65
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_full        28.28
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17

_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.
;

_reflns_number_total             3330
_reflns_number_gt                2176
_reflns_threshold_expression     >2sigma(I)

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1268
_refine_ls_R_factor_gt           0.0908
_refine_ls_wR_factor_gt          0.1919
_refine_ls_wR_factor_ref         0.2093
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.073
_refine_ls_number_reflns         3330
_refine_ls_number_parameters     210
_refine_ls_number_restraints     12
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0100P)^2^+1.1000P] where P=(Fo^2^+2Fc^2^)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.395
_refine_diff_density_min         -0.252
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.141(8)

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'

_computing_data_collection       ?
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C2B 1.119(4) 0.792(3) 0.3307(17) 0.100(7) Uani d PU 0.5 A 1
C C3B 0.906(4) 0.678(3) 0.3156(19) 0.076(7) Uani d P 0.5 A 1
C C11B 1.2675(13) 0.7382(15) 0.4011(7) 0.087(3) Uani d P 0.5 A 1
C C12B 1.2148(14) 0.8024(15) 0.5184(6) 0.082(3) Uani d P 0.5 A 1
C C13B 1.3534(19) 0.6982(19) 0.5784(9) 0.119(4) Uani d P 0.5 A 1
C C2A 1.1250(18) 0.7925(13) 0.3257(8) 0.036(3) Uani d PU 0.5 A 2
C C3A 0.925(3) 0.707(3) 0.3072(12) 0.037(3) Uani d P 0.5 A 2
C C11A 1.2135(10) 0.8900(9) 0.4368(5) 0.0583(19) Uani d P 0.5 A 2
C C12A 1.3522(18) 0.7782(16) 0.4892(8) 0.099(3) Uani d P 0.5 A 2
C C13A 1.264(2) 0.6190(17) 0.5085(9) 0.105(4) Uani d P 0.5 A 2
C C1 1.2000(5) 0.7570(4) 0.2198(3) 0.0538(9) Uani d . 1 . .
C C4 0.9031(5) 0.6046(4) 0.1955(3) 0.0499(8) Uani d . 1 . .
C C5 0.7400(5) 0.4839(4) 0.1393(3) 0.0487(8) Uani d . 1 A .
C C6 0.5607(5) 0.4256(4) 0.1762(3) 0.0529(8) Uani d . 1 . .
H H6 0.5216 0.4624 0.2476 0.063 Uiso calc R 1 A .
C C7 0.4513(5) 0.3070(4) 0.0927(3) 0.0495(8) Uani d . 1 A .
C C8 0.5676(5) 0.2917(4) -0.0002(3) 0.0499(8) Uani d . 1 . .
C C9 0.5162(5) 0.1880(4) -0.1041(3) 0.0536(9) Uani d . 1 . .
H H9 0.3915 0.1173 -0.1123 0.064 Uiso calc R 1 . .
C C10 1.3841(5) 0.8309(4) 0.1993(3) 0.0531(9) Uani d . 1 . .
H H10 1.456 0.9086 0.2609 0.064 Uiso calc R 1 . .
C C14 0.2475(5) 0.2091(4) 0.0910(3) 0.0562(9) Uani d . 1 . .
H H14A 0.2533 0.0851 0.0587 0.067 Uiso calc R 1 A .
H H14B 0.1546 0.2481 0.0433 0.067 Uiso calc R 1 . .
C C15 0.1649(5) 0.2287(4) 0.1990(3) 0.0608(9) Uani d . 1 A .
H H15A 0.1523 0.3517 0.2304 0.073 Uiso calc R 1 . .
H H15B 0.2589 0.1934 0.2479 0.073 Uiso calc R 1 . .
C C16 -0.0365(5) 0.1217(5) 0.1924(3) 0.0638(10) Uani d . 1 . .
H H16A -0.1325 0.1615 0.1481 0.096 Uiso calc R 1 A .
H H16B -0.0815 0.1343 0.2652 0.096 Uiso calc R 1 . .
H H16C -0.0256 0.0001 0.1596 0.096 Uiso calc R 1 . .
N N1 1.0673(3) 0.6446(3) 0.14590(19) 0.0413(6) Uani d . 1 A .
H H1 1.0848 0.6043 0.077 0.05 Uiso calc PR 0.5 . .
N N2 0.7428(4) 0.4028(3) 0.0341(2) 0.0454(7) Uani d . 1 A .
H H2 0.8407 0.4179 -0.0066 0.054 Uiso calc PR 0.5 . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
C2B 0.102(10) 0.112(10) 0.100(9) 0.044(8) 0.020(7) 0.038(7)
C3B 0.067(12) 0.051(8) 0.098(13) 0.009(7) -0.025(8) 0.000(7)
C11B 0.072(6) 0.134(9) 0.059(5) 0.007(5) -0.007(4) 0.034(5)
C12B 0.063(5) 0.146(10) 0.029(4) -0.003(6) -0.004(4) 0.014(4)
C13B 0.127(10) 0.164(12) 0.076(7) 0.051(9) -0.012(7) 0.038(8)
C2A 0.042(4) 0.034(4) 0.020(3) 0.007(3) -0.020(3) -0.012(3)
C3A 0.033(5) 0.046(7) 0.025(4) -0.006(4) 0.006(3) 0.001(4)
C11A 0.050(4) 0.059(4) 0.043(4) 0.007(3) -0.011(3) -0.028(3)
C12A 0.097(8) 0.124(9) 0.054(6) -0.010(7) -0.029(5) -0.001(5)
C13A 0.130(10) 0.124(9) 0.065(6) 0.030(8) -0.013(6) 0.029(6)
C1 0.0532(19) 0.0405(16) 0.060(2) 0.0120(14) -0.0183(16) 0.0007(14)
C4 0.0485(18) 0.0402(15) 0.057(2) 0.0102(13) -0.0149(15) 0.0070(14)
C5 0.0486(18) 0.0389(15) 0.057(2) 0.0113(13) -0.0144(14) 0.0108(14)
C6 0.0534(19) 0.0419(16) 0.062(2) 0.0096(14) -0.0131(15) 0.0116(14)
C7 0.0443(17) 0.0402(15) 0.065(2) 0.0075(13) -0.0110(15) 0.0165(14)
C8 0.0557(19) 0.0351(14) 0.0570(19) 0.0131(13) -0.0192(15) 0.0091(13)
C9 0.0421(17) 0.0423(16) 0.070(2) 0.0025(13) -0.0166(16) 0.0073(15)
C10 0.0433(17) 0.0401(16) 0.065(2) 0.0039(13) -0.0192(15) -0.0012(14)
C14 0.055(2) 0.0447(17) 0.068(2) 0.0074(15) -0.0129(16) 0.0142(15)
C15 0.061(2) 0.0475(18) 0.074(2) 0.0108(16) -0.0079(18) 0.0168(17)
C16 0.055(2) 0.058(2) 0.080(3) 0.0059(16) -0.0017(18) 0.0224(18)
N1 0.0420(14) 0.0350(12) 0.0430(13) 0.0056(10) -0.0115(11) 0.0051(10)
N2 0.0414(13) 0.0352(12) 0.0573(16) 0.0046(10) -0.0150(11) 0.0111(11)

_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C2B C11B . 1.50(2) ?
C2B C3B . 1.60(3) ?
C2B C1 . 1.52(2) ?
C3B C4 . 1.50(2) ?
C11B C12B . 1.536(12) ?
C12B C13B . 1.624(15) ?
C2A C1 . 1.445(14) ?
C2A C3A . 1.43(2) ?
C2A C11A . 1.504(9) ?
C3A C4 . 1.455(16) ?
C11A C12A . 1.614(14) ?
C12A C13A . 1.437(16) ?
C1 N1 . 1.355(4) ?
C1 C10 . 1.387(5) ?
C4 N1 . 1.354(4) ?
C4 C5 . 1.422(4) ?
C5 N2 . 1.346(4) ?
C5 C6 . 1.399(5) ?
C6 C7 . 1.366(4) ?
C6 H6 . 0.95 ?
C7 C8 . 1.446(5) ?
C7 C14 . 1.508(4) ?
C8 C9 . 1.389(4) ?
C8 N2 . 1.386(4) ?
C9 C10 2_765 1.406(5) ?
C9 H9 . 0.95 ?
C10 C9 2_765 1.406(5) ?
C10 H10 . 0.95 ?
C14 C15 . 1.497(5) ?
C14 H14A . 0.99 ?
C14 H14B . 0.99 ?
C15 C16 . 1.518(5) ?
C15 H15A . 0.99 ?
C15 H15B . 0.99 ?
C16 H16A . 0.98 ?
C16 H16B . 0.98 ?
C16 H16C . 0.98 ?
N1 H1 . 0.88 ?
N2 H2 . 0.88 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C11B C2B C3B . . 113.2(19) ?
C11B C2B C1 . . 104.9(15) ?
C3B C2B C1 . . 106.2(14) ?
C4 C3B C2B . . 96.9(15) ?
C2B C11B C12B . . 107.2(12) ?
C11B C12B C13B . . 100.5(9) ?
C1 C2A C3A . . 104.1(7) ?
C1 C2A C11A . . 133.9(10) ?
C3A C2A C11A . . 122.0(12) ?
C2A C3A C4 . . 106.3(10) ?
C2A C11A C12A . . 111.8(7) ?
C13A C12A C11A . . 118.9(10) ?
N1 C1 C2A . . 111.0(5) ?
N1 C1 C10 . . 125.9(3) ?
C2A C1 C10 . . 123.1(5) ?
N1 C1 C2B . . 110.2(9) ?
C2A C1 C2B . . 0.8(12) ?
C10 C1 C2B . . 123.9(9) ?
N1 C4 C5 . . 121.9(3) ?
N1 C4 C3B . . 117.8(10) ?
C5 C4 C3B . . 120.0(10) ?
N1 C4 C3A . . 109.0(7) ?
C5 C4 C3A . . 129.1(8) ?
C3B C4 C3A . . 11.5(16) ?
N2 C5 C6 . . 108.6(3) ?
N2 C5 C4 . . 121.3(3) ?
C6 C5 C4 . . 130.1(3) ?
C7 C6 C5 . . 108.8(3) ?
C7 C6 H6 . . 125.6 ?
C5 C6 H6 . . 125.6 ?
C6 C7 C8 . . 106.6(3) ?
C6 C7 C14 . . 129.2(3) ?
C8 C7 C14 . . 124.2(3) ?
C9 C8 N2 . . 126.0(3) ?
C9 C8 C7 . . 127.5(3) ?
N2 C8 C7 . . 106.5(3) ?
C8 C9 C10 . 2_765 131.4(3) ?
C8 C9 H9 . . 114.3 ?
C10 C9 H9 2_765 . 114.3 ?
C1 C10 C9 . 2_765 131.8(3) ?
C1 C10 H10 . . 114.1 ?
C9 C10 H10 2_765 . 114.1 ?
C7 C14 C15 . . 115.0(3) ?
C7 C14 H14A . . 108.5 ?
C15 C14 H14A . . 108.5 ?
C7 C14 H14B . . 108.5 ?
C15 C14 H14B . . 108.5 ?
H14A C14 H14B . . 107.5 ?
C14 C15 C16 . . 112.4(3) ?
C14 C15 H15A . . 109.1 ?
C16 C15 H15A . . 109.1 ?
C14 C15 H15B . . 109.1 ?
C16 C15 H15B . . 109.1 ?
H15A C15 H15B . . 107.8 ?
C15 C16 H16A . . 109.5 ?
C15 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
C15 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
C4 N1 C1 . . 108.8(3) ?
C4 N1 H1 . . 125.6 ?
C1 N1 H1 . . 125.6 ?
C5 N2 C8 . . 109.5(3) ?
C5 N2 H2 . . 125.2 ?
C8 N2 H2 . . 125.2 ?