# Electronic Supplementary Material (ESI) for Organic .
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_shelxl

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H17 N4 O, 0.5(C6 H6)'
_chemical_formula_sum            'C29 H20 N4 O'
_chemical_formula_weight         440.49

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   7.8405(13)
_cell_length_b                   9.2163(12)
_cell_length_c                   15.484(2)
_cell_angle_alpha                96.813(11)
_cell_angle_beta                 90.713(13)
_cell_angle_gamma                104.161(13)
_cell_volume                     1076.2(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2354
_cell_measurement_theta_min      4.9844
_cell_measurement_theta_max      67.2780

_exptl_crystal_description       rods
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             460
_exptl_absorpt_coefficient_mu    0.672
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.84852
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
'Empirical absorption correction (CrysAlis RED, Oxford Diffraction)'


_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4223
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6475
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_av_sigmaI/netI    0.0393
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         4.99
_diffrn_reflns_theta_max         66.99
_reflns_number_total             3820
_reflns_number_gt                2999
_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 F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.0775P)²+0.0000P] where P=(Fo²+2Fc²)/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         3820
_refine_ls_number_parameters     307
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0610
_refine_ls_R_factor_gt           0.0471
_refine_ls_wR_factor_ref         0.1323
_refine_ls_wR_factor_gt          0.1211
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_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
C1 C -0.15238(19) 0.21678(18) 0.70847(11) 0.0252(3) Uani 1 1 d . . .
C2 C 0.0144(2) 0.33708(18) 0.60481(11) 0.0258(4) Uani 1 1 d . . .
C3 C 0.0886(2) 0.33182(18) 0.52341(11) 0.0261(4) Uani 1 1 d . . .
H3 H 0.0596 0.2443 0.4840 0.031 Uiso 1 1 calc R . .
C4 C 0.2074(2) 0.46130(18) 0.50275(11) 0.0253(3) Uani 1 1 d . . .
C5 C 0.3929(2) 0.63029(18) 0.44712(11) 0.0256(4) Uani 1 1 d . . .
C6 C 0.24688(19) 0.59043(18) 0.56359(11) 0.0254(3) Uani 1 1 d . . .
C7 C 0.1804(2) 0.60261(18) 0.64431(11) 0.0260(3) Uani 1 1 d . . .
H7 H 0.2119 0.6910 0.6830 0.031 Uiso 1 1 calc R . .
C8 C 0.0610(2) 0.47243(19) 0.66488(11) 0.0259(4) Uani 1 1 d . . .
C9 C 0.0208(2) 0.59137(18) 0.81238(11) 0.0263(4) Uani 1 1 d . . .
C10 C -0.0215(2) 0.72417(19) 0.79761(12) 0.0300(4) Uani 1 1 d . . .
H10 H -0.0716 0.7323 0.7442 0.036 Uiso 1 1 calc R . .
C11 C 0.0118(2) 0.8448(2) 0.86341(13) 0.0353(4) Uani 1 1 d . . .
H11 H -0.0157 0.9345 0.8541 0.042 Uiso 1 1 calc R . .
C12 C 0.0856(2) 0.8319(2) 0.94254(13) 0.0366(4) Uani 1 1 d . . .
H12 H 0.1095 0.9133 0.9863 0.044 Uiso 1 1 calc R . .
C13 C 0.1243(2) 0.6971(2) 0.95694(12) 0.0357(4) Uani 1 1 d . . .
H13 H 0.1719 0.6880 1.0108 0.043 Uiso 1 1 calc R . .
C14 C 0.0923(2) 0.5765(2) 0.89155(12) 0.0308(4) Uani 1 1 d . . .
H14 H 0.1188 0.4864 0.9010 0.037 Uiso 1 1 calc R . .
C15 C -0.2644(2) 0.07718(19) 0.73776(11) 0.0266(4) Uani 1 1 d . . .
C16 C -0.3401(2) 0.0801(2) 0.81799(12) 0.0307(4) Uani 1 1 d . . .
H16 H -0.3221 0.1709 0.8543 0.037 Uiso 1 1 calc R . .
C17 C -0.4429(2) -0.0511(2) 0.84499(12) 0.0333(4) Uani 1 1 d . . .
H17 H -0.4934 -0.0478 0.8990 0.040 Uiso 1 1 calc R . .
C18 C -0.4696(2) -0.1865(2) 0.79127(12) 0.0322(4) Uani 1 1 d . . .
H18 H -0.5380 -0.2745 0.8091 0.039 Uiso 1 1 calc R . .
C19 C -0.3944(2) -0.19082(19) 0.71116(12) 0.0312(4) Uani 1 1 d . . .
H19 H -0.4123 -0.2819 0.6751 0.037 Uiso 1 1 calc R . .
C20 C -0.2918(2) -0.05952(19) 0.68402(12) 0.0289(4) Uani 1 1 d . . .
H20 H -0.2417 -0.0631 0.6300 0.035 Uiso 1 1 calc R . .
C21 C 0.5192(2) 0.72259(18) 0.39488(11) 0.0258(4) Uani 1 1 d . . .
C22 C 0.6063(2) 0.87010(19) 0.42736(12) 0.0296(4) Uani 1 1 d . . .
H22 H 0.5831 0.9106 0.4826 0.035 Uiso 1 1 calc R . .
C23 C 0.7269(2) 0.9565(2) 0.37774(13) 0.0351(4) Uani 1 1 d . . .
H23 H 0.7836 1.0553 0.3994 0.042 Uiso 1 1 calc R . .
C24 C 0.7633(2) 0.8959(2) 0.29584(13) 0.0357(4) Uani 1 1 d . . .
H24 H 0.8445 0.9539 0.2625 0.043 Uiso 1 1 calc R . .
C25 C 0.6784(2) 0.7487(2) 0.26367(12) 0.0331(4) Uani 1 1 d . . .
H25 H 0.7042 0.7080 0.2090 0.040 Uiso 1 1 calc R . .
C26 C 0.5553(2) 0.66163(19) 0.31225(11) 0.0294(4) Uani 1 1 d . . .
H26 H 0.4973 0.5635 0.2900 0.035 Uiso 1 1 calc R . .
C27 C 0.4265(2) 0.5449(2) 0.07639(13) 0.0365(4) Uani 1 1 d . . .
H27 H 0.3776 0.5755 0.1277 0.044 Uiso 1 1 calc R . .
C28 C 0.3773(2) 0.3963(2) 0.03973(13) 0.0358(4) Uani 1 1 d . . .
H28 H 0.2949 0.3266 0.0663 0.043 Uiso 1 1 calc R . .
C29 C 0.4501(2) 0.3507(2) -0.03644(13) 0.0380(4) Uani 1 1 d . . .
H29 H 0.4168 0.2503 -0.0611 0.046 Uiso 1 1 calc R . .
N1 N -0.01367(17) 0.46560(15) 0.74491(9) 0.0259(3) Uani 1 1 d . . .
N2 N -0.11523(17) 0.33606(15) 0.77009(9) 0.0273(3) Uani 1 1 d . . .
N3 N -0.10075(17) 0.20989(16) 0.62705(9) 0.0267(3) Uani 1 1 d . . .
N4 N 0.30435(17) 0.49129(15) 0.42891(9) 0.0264(3) Uani 1 1 d . . .
O1 O 0.36593(14) 0.70033(13) 0.52791(7) 0.0262(3) Uani 1 1 d . . .


_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
C1 N3 1.328(2) . ?
C1 N2 1.338(2) . ?
C1 C15 1.493(2) . ?
C2 N3 1.376(2) . ?
C2 C3 1.395(2) . ?
C2 C8 1.431(2) . ?
C3 C4 1.396(2) . ?
C3 H3 0.9300 . ?
C4 C6 1.395(2) . ?
C4 N4 1.398(2) . ?
C5 N4 1.295(2) . ?
C5 O1 1.381(2) . ?
C5 C21 1.460(2) . ?
C6 C7 1.363(2) . ?
C6 O1 1.3731(19) . ?
C7 C8 1.402(2) . ?
C7 H7 0.9300 . ?
C8 N1 1.379(2) . ?
C9 C14 1.377(3) . ?
C9 C10 1.387(2) . ?
C9 N1 1.435(2) . ?
C10 C11 1.387(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.379(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.390(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.384(2) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C16 1.384(2) . ?
C15 C20 1.393(2) . ?
C16 C17 1.392(2) . ?
C16 H16 0.9300 . ?
C17 C18 1.384(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.380(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.393(2) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 C22 1.394(2) . ?
C21 C26 1.396(2) . ?
C22 C23 1.383(2) . ?
C22 H22 0.9300 . ?
C23 C24 1.386(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.386(3) . ?
C24 H24 0.9300 . ?
C25 C26 1.387(2) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C27 C28 1.377(3) . ?
C27 C29 1.395(3) 2_665 ?
C27 H27 0.9300 . ?
C28 C29 1.382(3) . ?
C28 H28 0.9300 . ?
C29 C27 1.395(3) 2_665 ?
C29 H29 0.9300 . ?
N1 N2 1.3654(19) . ?

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
N3 C1 N2 127.73(15) . . ?
N3 C1 C15 118.21(15) . . ?
N2 C1 C15 114.06(15) . . ?
N3 C2 C3 119.18(15) . . ?
N3 C2 C8 120.66(16) . . ?
C3 C2 C8 120.14(15) . . ?
C2 C3 C4 118.25(15) . . ?
C2 C3 H3 120.9 . . ?
C4 C3 H3 120.9 . . ?
C6 C4 C3 119.13(15) . . ?
C6 C4 N4 108.81(14) . . ?
C3 C4 N4 132.06(16) . . ?
N4 C5 O1 115.43(15) . . ?
N4 C5 C21 129.11(16) . . ?
O1 C5 C21 115.45(14) . . ?
C7 C6 O1 126.78(15) . . ?
C7 C6 C4 125.54(15) . . ?
O1 C6 C4 107.68(14) . . ?
C6 C7 C8 115.21(15) . . ?
C6 C7 H7 122.4 . . ?
C8 C7 H7 122.4 . . ?
N1 C8 C7 122.11(15) . . ?
N1 C8 C2 116.13(15) . . ?
C7 C8 C2 121.72(16) . . ?
C14 C9 C10 121.17(16) . . ?
C14 C9 N1 119.05(15) . . ?
C10 C9 N1 119.76(15) . . ?
C9 C10 C11 119.26(17) . . ?
C9 C10 H10 120.4 . . ?
C11 C10 H10 120.4 . . ?
C12 C11 C10 120.07(17) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C12 C13 120.02(17) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C14 C13 C12 120.30(17) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C9 C14 C13 119.17(17) . . ?
C9 C14 H14 120.4 . . ?
C13 C14 H14 120.4 . . ?
C16 C15 C20 119.06(16) . . ?
C16 C15 C1 121.33(15) . . ?
C20 C15 C1 119.60(15) . . ?
C15 C16 C17 120.82(16) . . ?
C15 C16 H16 119.6 . . ?
C17 C16 H16 119.6 . . ?
C18 C17 C16 119.82(17) . . ?
C18 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
C19 C18 C17 119.85(16) . . ?
C19 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C18 C19 C20 120.38(17) . . ?
C18 C19 H19 119.8 . . ?
C20 C19 H19 119.8 . . ?
C19 C20 C15 120.08(16) . . ?
C19 C20 H20 120.0 . . ?
C15 C20 H20 120.0 . . ?
C22 C21 C26 119.76(16) . . ?
C22 C21 C5 120.57(16) . . ?
C26 C21 C5 119.66(15) . . ?
C23 C22 C21 120.23(17) . . ?
C23 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C22 C23 C24 120.06(17) . . ?
C22 C23 H23 120.0 . . ?
C24 C23 H23 120.0 . . ?
C23 C24 C25 119.88(17) . . ?
C23 C24 H24 120.1 . . ?
C25 C24 H24 120.1 . . ?
C24 C25 C26 120.63(17) . . ?
C24 C25 H25 119.7 . . ?
C26 C25 H25 119.7 . . ?
C25 C26 C21 119.42(17) . . ?
C25 C26 H26 120.3 . . ?
C21 C26 H26 120.3 . . ?
C28 C27 C29 119.88(18) . 2_665 ?
C28 C27 H27 120.1 . . ?
C29 C27 H27 120.1 2_665 . ?
C27 C28 C29 120.10(18) . . ?
C27 C28 H28 120.0 . . ?
C29 C28 H28 119.9 . . ?
C28 C29 C27 120.02(19) . 2_665 ?
C28 C29 H29 120.0 . . ?
C27 C29 H29 120.0 2_665 . ?
N2 N1 C8 123.34(14) . . ?
N2 N1 C9 113.56(13) . . ?
C8 N1 C9 122.88(14) . . ?
C1 N2 N1 115.30(14) . . ?
C1 N3 C2 116.38(14) . . ?
C5 N4 C4 104.26(14) . . ?
C6 O1 C5 103.83(13) . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        66.99
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.053
_database_code_depnum_ccdc_archive 'CCDC 940088'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_shelxl

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C32 H22 N5'
_chemical_formula_sum            'C32 H22 N5'
_chemical_formula_weight         476.55

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 '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                   7.8924(8)
_cell_length_b                   11.3721(9)
_cell_length_c                   13.2802(12)
_cell_angle_alpha                96.019(7)
_cell_angle_beta                 90.262(8)
_cell_angle_gamma                96.237(8)
_cell_volume                     1178.20(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    100.05(10)
_cell_measurement_reflns_used    3878
_cell_measurement_theta_min      3.3440
_cell_measurement_theta_max      72.4672


_exptl_crystal_description       rectangle
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             498
_exptl_absorpt_coefficient_mu    0.638
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.85362
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
'Empirical absorption correction (CrysAlis RED, Oxford Diffraction)'


_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4223
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7408
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_av_sigmaI/netI    0.0324
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.35
_diffrn_reflns_theta_max         66.98
_reflns_number_total             4186
_reflns_number_gt                3520
_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 F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.0930P)²+0.0000P] where P=(Fo²+2Fc²)/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         4186
_refine_ls_number_parameters     334
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0526
_refine_ls_R_factor_gt           0.0452
_refine_ls_wR_factor_ref         0.1357
_refine_ls_wR_factor_gt          0.1272
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_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
C1 C 0.47820(18) 0.71688(13) 0.82554(11) 0.0227(3) Uani 1 1 d . . .
C2 C 0.37467(18) 0.59421(13) 0.68451(11) 0.0224(3) Uani 1 1 d . . .
C3 C 0.33356(19) 0.48078(12) 0.63370(11) 0.0241(3) Uani 1 1 d . . .
H3 H 0.3492 0.4135 0.6654 0.029 Uiso 1 1 calc R . .
C4 C 0.26867(18) 0.46951(12) 0.53471(11) 0.0226(3) Uani 1 1 d . . .
C5 C 0.17074(18) 0.40999(12) 0.38358(11) 0.0224(3) Uani 1 1 d . . .
C6 C 0.24844(18) 0.57354(13) 0.48799(11) 0.0219(3) Uani 1 1 d . . .
C7 C 0.28933(18) 0.68697(12) 0.53522(11) 0.0229(3) Uani 1 1 d . . .
H7 H 0.2785 0.7536 0.5017 0.027 Uiso 1 1 calc R . .
C8 C 0.34741(18) 0.69761(12) 0.63495(11) 0.0215(3) Uani 1 1 d . . .
C9 C 0.36960(18) 0.91857(12) 0.65446(11) 0.0222(3) Uani 1 1 d . . .
C10 C 0.22204(19) 0.94088(13) 0.60614(11) 0.0248(3) Uani 1 1 d . . .
H10 H 0.1279 0.8838 0.5993 0.030 Uiso 1 1 calc R . .
C11 C 0.2168(2) 1.04964(13) 0.56808(12) 0.0278(3) Uani 1 1 d . . .
H1 H 0.1192 1.0643 0.5342 0.033 Uiso 1 1 calc R . .
C12 C 0.3547(2) 1.13663(13) 0.57984(11) 0.0273(3) Uani 1 1 d . . .
H12 H 0.3509 1.2085 0.5528 0.033 Uiso 1 1 calc R . .
C13 C 0.4981(2) 1.11497(13) 0.63235(11) 0.0271(3) Uani 1 1 d . . .
H13 H 0.5893 1.1742 0.6430 0.033 Uiso 1 1 calc R . .
C14 C 0.50755(19) 1.00627(13) 0.66923(11) 0.0250(3) Uani 1 1 d . . .
H14 H 0.6050 0.9920 0.7035 0.030 Uiso 1 1 calc R . .
C15 C 0.55286(18) 0.73421(13) 0.92962(11) 0.0242(3) Uani 1 1 d . . .
C16 C 0.5680(2) 0.84609(14) 0.98572(12) 0.0319(4) Uani 1 1 d . . .
H16 H 0.5330 0.9108 0.9571 0.038 Uiso 1 1 calc R . .
C17 C 0.6347(2) 0.86170(15) 1.08376(12) 0.0344(4) Uani 1 1 d . . .
H17 H 0.6445 0.9365 1.1204 0.041 Uiso 1 1 calc R . .
C18 C 0.6866(2) 0.76548(16) 1.12673(12) 0.0341(4) Uani 1 1 d . . .
H18 H 0.7287 0.7753 1.1929 0.041 Uiso 1 1 calc R . .
C19 C 0.6759(2) 0.65488(16) 1.07137(12) 0.0348(4) Uani 1 1 d . . .
H19 H 0.7138 0.5909 1.0998 0.042 Uiso 1 1 calc R . .
C20 C 0.6086(2) 0.63890(14) 0.97328(12) 0.0290(3) Uani 1 1 d . . .
H20 H 0.6009 0.5641 0.9367 0.035 Uiso 1 1 calc R . .
C21 C 0.10748(18) 0.33080(13) 0.29319(11) 0.0232(3) Uani 1 1 d . . .
C22 C 0.00183(19) 0.36438(13) 0.21865(11) 0.0262(3) Uani 1 1 d . . .
H22 H -0.0304 0.4410 0.2243 0.031 Uiso 1 1 calc R . .
C23 C -0.05507(19) 0.28427(14) 0.13652(12) 0.0295(3) Uani 1 1 d . . .
H23 H -0.1244 0.3078 0.0872 0.035 Uiso 1 1 calc R . .
C24 C -0.0093(2) 0.16911(14) 0.12730(13) 0.0322(4) Uani 1 1 d . . .
H24 H -0.0477 0.1157 0.0720 0.039 Uiso 1 1 calc R . .
C25 C 0.0937(2) 0.13434(14) 0.20079(13) 0.0314(4) Uani 1 1 d . . .
H25 H 0.1242 0.0572 0.1950 0.038 Uiso 1 1 calc R . .
C26 C 0.15189(19) 0.21426(13) 0.28332(12) 0.0265(3) Uani 1 1 d . . .
H26 H 0.2209 0.1901 0.3324 0.032 Uiso 1 1 calc R . .
C27 C 0.17171(18) 0.61303(12) 0.31512(11) 0.0218(3) Uani 1 1 d . . .
C28 C 0.06716(18) 0.70379(12) 0.33353(11) 0.0236(3) Uani 1 1 d . . .
H28 H 0.0022 0.7094 0.3917 0.028 Uiso 1 1 calc R . .
C29 C 0.06178(19) 0.78580(13) 0.26331(12) 0.0266(3) Uani 1 1 d . . .
H29 H -0.0042 0.8486 0.2757 0.032 Uiso 1 1 calc R . .
C30 C 0.1543(2) 0.77458(13) 0.17485(11) 0.0281(3) Uani 1 1 d . . .
H30 H 0.1478 0.8286 0.1274 0.034 Uiso 1 1 calc R . .
C31 C 0.25654(19) 0.68285(13) 0.15711(11) 0.0268(3) Uani 1 1 d . . .
H31 H 0.3172 0.6749 0.0973 0.032 Uiso 1 1 calc R . .
C32 C 0.26846(18) 0.60293(12) 0.22855(11) 0.0240(3) Uani 1 1 d . . .
H32 H 0.3405 0.5434 0.2183 0.029 Uiso 1 1 calc R . .
N1 N 0.38414(15) 0.80682(10) 0.69263(9) 0.0226(3) Uani 1 1 d . . .
N2 N 0.45315(16) 0.81850(11) 0.78786(9) 0.0240(3) Uani 1 1 d . . .
N3 N 0.44125(16) 0.60635(11) 0.78146(9) 0.0241(3) Uani 1 1 d . . .
N4 N 0.18683(15) 0.53380(10) 0.39120(9) 0.0222(3) Uani 1 1 d . . .
N5 N 0.21745(16) 0.36972(10) 0.46821(9) 0.0244(3) Uani 1 1 d . . .


_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
C1 N3 1.3313(19) . ?
C1 N2 1.3397(19) . ?
C1 C15 1.486(2) . ?
C2 N3 1.3760(19) . ?
C2 C3 1.396(2) . ?
C2 C8 1.4416(19) . ?
C3 C4 1.397(2) . ?
C3 H3 0.9300 . ?
C4 N5 1.3849(19) . ?
C4 C6 1.4156(19) . ?
C5 N5 1.3227(19) . ?
C5 N4 1.3928(18) . ?
C5 C21 1.474(2) . ?
C6 C7 1.378(2) . ?
C6 N4 1.3849(19) . ?
C7 C8 1.388(2) . ?
C7 H7 0.9300 . ?
C8 N1 1.3904(18) . ?
C9 C10 1.387(2) . ?
C9 C14 1.393(2) . ?
C9 N1 1.4323(18) . ?
C10 C11 1.389(2) . ?
C10 H10 0.9300 . ?
C11 C12 1.385(2) . ?
C11 H1 0.9300 . ?
C12 C13 1.385(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.386(2) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C20 1.392(2) . ?
C15 C16 1.398(2) . ?
C16 C17 1.389(2) . ?
C16 H16 0.9300 . ?
C17 C18 1.384(2) . ?
C17 H17 0.9300 . ?
C18 C19 1.383(2) . ?
C18 H18 0.9300 . ?
C19 C20 1.391(2) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 C26 1.400(2) . ?
C21 C22 1.401(2) . ?
C22 C23 1.386(2) . ?
C22 H22 0.9300 . ?
C23 C24 1.389(2) . ?
C23 H23 0.9300 . ?
C24 C25 1.383(2) . ?
C24 H24 0.9300 . ?
C25 C26 1.391(2) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C27 C32 1.385(2) . ?
C27 C28 1.393(2) . ?
C27 N4 1.4352(18) . ?
C28 C29 1.390(2) . ?
C28 H28 0.9300 . ?
C29 C30 1.388(2) . ?
C29 H29 0.9300 . ?
C30 C31 1.389(2) . ?
C30 H30 0.9300 . ?
C31 C32 1.391(2) . ?
C31 H31 0.9300 . ?
C32 H32 0.9300 . ?
N1 N2 1.3626(17) . ?

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
N3 C1 N2 127.62(14) . . ?
N3 C1 C15 118.52(13) . . ?
N2 C1 C15 113.84(13) . . ?
N3 C2 C3 119.69(13) . . ?
N3 C2 C8 120.55(13) . . ?
C3 C2 C8 119.76(13) . . ?
C2 C3 C4 119.22(13) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
N5 C4 C3 131.11(13) . . ?
N5 C4 C6 109.79(13) . . ?
C3 C4 C6 119.10(13) . . ?
N5 C5 N4 112.20(13) . . ?
N5 C5 C21 122.82(13) . . ?
N4 C5 C21 124.97(13) . . ?
C7 C6 N4 131.12(13) . . ?
C7 C6 C4 123.39(13) . . ?
N4 C6 C4 105.47(12) . . ?
C6 C7 C8 117.24(13) . . ?
C6 C7 H7 121.4 . . ?
C8 C7 H7 121.4 . . ?
C7 C8 N1 122.82(13) . . ?
C7 C8 C2 121.17(13) . . ?
N1 C8 C2 116.00(13) . . ?
C10 C9 C14 120.43(13) . . ?
C10 C9 N1 121.61(13) . . ?
C14 C9 N1 117.94(13) . . ?
C9 C10 C11 119.13(14) . . ?
C9 C10 H10 120.4 . . ?
C11 C10 H10 120.4 . . ?
C12 C11 C10 121.05(14) . . ?
C12 C11 H1 119.5 . . ?
C10 C11 H1 119.5 . . ?
C13 C12 C11 119.07(13) . . ?
C13 C12 H12 120.5 . . ?
C11 C12 H12 120.5 . . ?
C12 C13 C14 120.86(14) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 H13 119.6 . . ?
C13 C14 C9 119.35(14) . . ?
C13 C14 H14 120.3 . . ?
C9 C14 H14 120.3 . . ?
C20 C15 C16 118.73(14) . . ?
C20 C15 C1 120.45(14) . . ?
C16 C15 C1 120.82(14) . . ?
C17 C16 C15 120.77(15) . . ?
C17 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
C18 C17 C16 119.75(15) . . ?
C18 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
C19 C18 C17 120.12(15) . . ?
C19 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C18 C19 C20 120.24(15) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 H19 119.9 . . ?
C19 C20 C15 120.36(15) . . ?
C19 C20 H20 119.8 . . ?
C15 C20 H20 119.8 . . ?
C26 C21 C22 118.45(14) . . ?
C26 C21 C5 117.74(13) . . ?
C22 C21 C5 123.77(13) . . ?
C23 C22 C21 120.51(14) . . ?
C23 C22 H22 119.7 . . ?
C21 C22 H22 119.7 . . ?
C22 C23 C24 120.48(15) . . ?
C22 C23 H23 119.8 . . ?
C24 C23 H23 119.8 . . ?
C25 C24 C23 119.66(15) . . ?
C25 C24 H24 120.2 . . ?
C23 C24 H24 120.2 . . ?
C24 C25 C26 120.26(15) . . ?
C24 C25 H25 119.9 . . ?
C26 C25 H25 119.9 . . ?
C25 C26 C21 120.63(15) . . ?
C25 C26 H26 119.7 . . ?
C21 C26 H26 119.7 . . ?
C32 C27 C28 121.35(13) . . ?
C32 C27 N4 119.88(12) . . ?
C28 C27 N4 118.64(13) . . ?
C29 C28 C27 118.76(14) . . ?
C29 C28 H28 120.6 . . ?
C27 C28 H28 120.6 . . ?
C30 C29 C28 120.41(13) . . ?
C30 C29 H29 119.8 . . ?
C28 C29 H29 119.8 . . ?
C29 C30 C31 120.10(14) . . ?
C29 C30 H30 120.0 . . ?
C31 C30 H30 120.0 . . ?
C30 C31 C32 120.11(14) . . ?
C30 C31 H31 119.9 . . ?
C32 C31 H31 119.9 . . ?
C27 C32 C31 119.19(13) . . ?
C27 C32 H32 120.4 . . ?
C31 C32 H32 120.4 . . ?
N2 N1 C8 123.11(12) . . ?
N2 N1 C9 113.17(11) . . ?
C8 N1 C9 123.43(12) . . ?
C1 N2 N1 115.86(12) . . ?
C1 N3 C2 116.70(12) . . ?
C6 N4 C5 106.63(12) . . ?
C6 N4 C27 122.30(12) . . ?
C5 N4 C27 130.46(12) . . ?
C5 N5 C4 105.89(12) . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        66.98
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.315
_refine_diff_density_rms         0.056
_database_code_depnum_ccdc_archive 'CCDC 940089'
