 
data_ra 
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety           'C20 H15 N3' 
_chemical_formula_sum 
 'C20 H15 N3 ' 
_chemical_formula_weight          297.35 
 
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' 
 'O'  'O'   0.0106   0.0060 
 '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_Hall      '-P 2ybc'
_symmetry_space_group_name_H-M       'P 21/c'
_symmetry_Int_Tables_number                 14

  
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x, y+1/2, -z+1/2' 
 '-x, -y, -z' 
 'x, -y-1/2, z-1/2' 
 
_cell_length_a                    10.5700(6) 
_cell_length_b                    12.2810(13) 
_cell_length_c                    12.1750(13) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  94.429(7) 
_cell_angle_gamma                 90.00 
_cell_volume                      1575.7(3) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     293(2) 
_cell_measurement_reflns_used     4811 
_cell_measurement_theta_min       2.97 
_cell_measurement_theta_max       25.02 


_exptl_crystal_description        'rectangular' 
_exptl_crystal_colour             'colourless' 
_exptl_crystal_size_max           0.270 
_exptl_crystal_size_mid           0.250 
_exptl_crystal_size_min           0.230 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.253 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              624 
_exptl_absorpt_coefficient_mu     0.076 
_exptl_absorpt_correction_type    none 
_exptl_absorpt_correction_T_min   ? 
_exptl_absorpt_correction_T_max   ? 
_exptl_absorpt_process_details    none 
  
_exptl_special_details 
; 
 ? 
; 
 
_diffrn_ambient_temperature       293 
_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   'MacScience DIPLabo 32001'
_diffrn_measurement_method        'ω scans' 
_diffrn_detector_area_resol_mean  10.0
_diffrn_standards_number          0 
_diffrn_standards_interval_count  . 
_diffrn_standards_interval_time   . 
_diffrn_standards_decay_%         ? 
_diffrn_reflns_number             4811 
_diffrn_reflns_av_R_equivalents   0.0236 
_diffrn_reflns_av_sigmaI/netI     0.0296 
_diffrn_reflns_limit_h_min        -10 
_diffrn_reflns_limit_h_max        11 
_diffrn_reflns_limit_k_min        -14 
_diffrn_reflns_limit_k_max        14 
_diffrn_reflns_limit_l_min        -14 
_diffrn_reflns_limit_l_max        14 
_diffrn_reflns_theta_min          2.97 
_diffrn_reflns_theta_max          25.02 
_reflns_number_total              2607 
_reflns_number_gt                 2093 
_reflns_threshold_expression      >2sigma(I) 
 
_computing_data_collection       
'XPRESS (MacScience, DIPLabo 32001, 2002)'
_computing_cell_refinement           
'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_reduction            
'DENZO and SCALEPACK (Otwinowski and Minor, 1997)'
_computing_structure_solution        'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement      'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics        
 'PLATON (Spek, 2003) ; ORTEP-II (Johnson, 1976)'
_computing_publication_material      'PLATON (Spek, 2003)' 

 
_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)+(0.0670P)²+0.1676P] 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      SHELXL 
_refine_ls_extinction_coef        0.036(6) 
_refine_ls_extinction_expression 
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^' 
_refine_ls_number_reflns          2607 
_refine_ls_number_parameters      209 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0572 
_refine_ls_R_factor_gt            0.0447 
_refine_ls_wR_factor_ref          0.1261 
_refine_ls_wR_factor_gt           0.1165 
_refine_ls_goodness_of_fit_ref    1.051 
_refine_ls_restrained_S_all       1.051 
_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 0.75681(11) 0.00396(10) 0.49811(9) 0.0518(4) Uani 1 1 d . . . 
N2 N 0.68764(12) 0.06221(10) 0.42027(10) 0.0554(4) Uani 1 1 d . . . 
C3 C 0.70806(14) 0.16623(12) 0.44792(12) 0.0504(4) Uani 1 1 d . . . 
C4 C 0.79080(15) 0.17402(12) 0.54354(13) 0.0528(4) Uani 1 1 d . . . 
H4 H 0.8196 0.2375 0.5788 0.063 Uiso 1 1 calc R . . 
C5 C 0.82061(14) 0.06929(12) 0.57448(12) 0.0496(4) Uani 1 1 d . . . 
C6 C 0.90521(14) 0.02892(12) 0.66746(12) 0.0497(4) Uani 1 1 d . . . 
C7 C 0.98861(15) -0.05756(12) 0.65923(13) 0.0554(4) Uani 1 1 d . . . 
H7 H 0.9915 -0.0953 0.5932 0.066 Uiso 1 1 calc R . . 
C8 C 1.06699(16) -0.08668(14) 0.75003(14) 0.0635(5) Uani 1 1 d . . . 
H8 H 1.1229 -0.1441 0.7423 0.076 Uiso 1 1 calc R . . 
N9 N 1.06846(15) -0.03849(13) 0.84807(12) 0.0728(5) Uani 1 1 d . . . 
C10 C 0.98793(19) 0.04452(15) 0.85467(14) 0.0726(5) Uani 1 1 d . . . 
H10 H 0.9868 0.0806 0.9218 0.087 Uiso 1 1 calc R . . 
C11 C 0.90660(16) 0.08016(13) 0.76874(13) 0.0606(4) Uani 1 1 d . . . 
H11 H 0.8526 0.1386 0.7786 0.073 Uiso 1 1 calc R . . 
C12 C 0.75255(14) -0.11225(13) 0.49410(12) 0.0535(4) Uani 1 1 d . . . 
C13 C 0.79349(16) -0.16549(14) 0.40360(14) 0.0640(5) Uani 1 1 d . . . 
H13 H 0.8200 -0.1263 0.3442 0.077 Uiso 1 1 calc R . . 
C14 C 0.79455(19) -0.27796(15) 0.40271(18) 0.0766(6) Uani 1 1 d . . . 
H14 H 0.8217 -0.3149 0.3421 0.092 Uiso 1 1 calc R . . 
C15 C 0.75576(19) -0.33546(16) 0.49074(19) 0.0812(6) Uani 1 1 d . . . 
H15 H 0.7592 -0.4111 0.4905 0.097 Uiso 1 1 calc R . . 
C16 C 0.7118(2) -0.28172(16) 0.57930(18) 0.0810(6) Uani 1 1 d . . . 
H16 H 0.6835 -0.3211 0.6379 0.097 Uiso 1 1 calc R . . 
C17 C 0.70960(17) -0.16957(14) 0.58123(14) 0.0666(5) Uani 1 1 d . . . 
H17 H 0.6795 -0.1329 0.6407 0.080 Uiso 1 1 calc R . . 
C18 C 0.64571(15) 0.25278(12) 0.37969(13) 0.0533(4) Uani 1 1 d . . . 
C19 C 0.63391(16) 0.35738(13) 0.42086(15) 0.0664(5) Uani 1 1 d . . . 
H19 H 0.6652 0.3736 0.4925 0.080 Uiso 1 1 calc R . . 
C20 C 0.57519(18) 0.43788(14) 0.35485(18) 0.0777(6) Uani 1 1 d . . . 
H20 H 0.5673 0.5079 0.3827 0.093 Uiso 1 1 calc R . . 
C21 C 0.52881(18) 0.41512(16) 0.24918(17) 0.0764(6) Uani 1 1 d . . . 
H21 H 0.4903 0.4697 0.2055 0.092 Uiso 1 1 calc R . . 
C22 C 0.53916(16) 0.31162(16) 0.20761(15) 0.0692(5) Uani 1 1 d . . . 
H22 H 0.5070 0.2959 0.1361 0.083 Uiso 1 1 calc R . . 
C23 C 0.59730(16) 0.23159(14) 0.27226(14) 0.0603(5) Uani 1 1 d . . . 
H23 H 0.6044 0.1618 0.2436 0.072 Uiso 1 1 calc R . . 
 
 
_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 N2 1.3555(16) . ? 
N1 C5 1.3661(18) . ? 
N1 C12 1.429(2) . ? 
N2 C3 1.3344(18) . ? 
C3 C4 1.404(2) . ? 
C3 C18 1.473(2) . ? 
C4 C5 1.370(2) . ? 
C4 H4 0.9300 . ? 
C5 C6 1.473(2) . ? 
C6 C11 1.383(2) . ? 
C6 C7 1.389(2) . ? 
C7 C8 1.377(2) . ? 
C7 H7 0.9300 . ? 
C8 N9 1.331(2) . ? 
C8 H8 0.9300 . ? 
N9 C10 1.334(2) . ? 
C10 C11 1.373(2) . ? 
C10 H10 0.9300 . ? 
C11 H11 0.9300 . ? 
C12 C17 1.379(2) . ? 
C12 C13 1.379(2) . ? 
C13 C14 1.381(2) . ? 
C13 H13 0.9300 . ? 
C14 C15 1.372(3) . ? 
C14 H14 0.9300 . ? 
C15 C16 1.375(3) . ? 
C15 H15 0.9300 . ? 
C16 C17 1.378(3) . ? 
C16 H16 0.9300 . ? 
C17 H17 0.9300 . ? 
C18 C19 1.388(2) . ? 
C18 C23 1.392(2) . ? 
C19 C20 1.390(2) . ? 
C19 H19 0.9300 . ? 
C20 C21 1.370(3) . ? 
C20 H20 0.9300 . ? 
C21 C22 1.376(3) . ? 
C21 H21 0.9300 . ? 
C22 C23 1.374(2) . ? 
C22 H22 0.9300 . ? 
C23 H23 0.9300 . ? 
 
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 
N2 N1 C5 112.16(12) . . ? 
N2 N1 C12 119.30(11) . . ? 
C5 N1 C12 128.51(12) . . ? 
C3 N2 N1 105.12(12) . . ? 
N2 C3 C4 110.65(13) . . ? 
N2 C3 C18 119.47(13) . . ? 
C4 C3 C18 129.89(13) . . ? 
C5 C4 C3 106.22(13) . . ? 
C5 C4 H4 126.9 . . ? 
C3 C4 H4 126.9 . . ? 
N1 C5 C4 105.86(13) . . ? 
N1 C5 C6 124.31(13) . . ? 
C4 C5 C6 129.81(14) . . ? 
C11 C6 C7 116.69(14) . . ? 
C11 C6 C5 119.72(14) . . ? 
C7 C6 C5 123.57(13) . . ? 
C8 C7 C6 119.12(15) . . ? 
C8 C7 H7 120.4 . . ? 
C6 C7 H7 120.4 . . ? 
N9 C8 C7 124.69(16) . . ? 
N9 C8 H8 117.7 . . ? 
C7 C8 H8 117.7 . . ? 
C8 N9 C10 115.48(15) . . ? 
N9 C10 C11 124.21(16) . . ? 
N9 C10 H10 117.9 . . ? 
C11 C10 H10 117.9 . . ? 
C10 C11 C6 119.79(16) . . ? 
C10 C11 H11 120.1 . . ? 
C6 C11 H11 120.1 . . ? 
C17 C12 C13 120.99(17) . . ? 
C17 C12 N1 119.67(15) . . ? 
C13 C12 N1 119.33(14) . . ? 
C12 C13 C14 118.92(17) . . ? 
C12 C13 H13 120.5 . . ? 
C14 C13 H13 120.5 . . ? 
C15 C14 C13 120.34(18) . . ? 
C15 C14 H14 119.8 . . ? 
C13 C14 H14 119.8 . . ? 
C14 C15 C16 120.32(19) . . ? 
C14 C15 H15 119.8 . . ? 
C16 C15 H15 119.8 . . ? 
C15 C16 C17 120.01(18) . . ? 
C15 C16 H16 120.0 . . ? 
C17 C16 H16 120.0 . . ? 
C16 C17 C12 119.36(18) . . ? 
C16 C17 H17 120.3 . . ? 
C12 C17 H17 120.3 . . ? 
C19 C18 C23 118.40(15) . . ? 
C19 C18 C3 120.86(14) . . ? 
C23 C18 C3 120.74(14) . . ? 
C18 C19 C20 119.87(17) . . ? 
C18 C19 H19 120.1 . . ? 
C20 C19 H19 120.1 . . ? 
C21 C20 C19 120.63(18) . . ? 
C21 C20 H20 119.7 . . ? 
C19 C20 H20 119.7 . . ? 
C20 C21 C22 120.08(17) . . ? 
C20 C21 H21 120.0 . . ? 
C22 C21 H21 120.0 . . ? 
C23 C22 C21 119.66(17) . . ? 
C23 C22 H22 120.2 . . ? 
C21 C22 H22 120.2 . . ? 
C22 C23 C18 121.36(17) . . ? 
C22 C23 H23 119.3 . . ? 
C18 C23 H23 119.3 . . ? 
 
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 
C5 N1 N2 C3 0.00(16) . . . . ? 
C12 N1 N2 C3 178.12(12) . . . . ? 
N1 N2 C3 C4 0.15(17) . . . . ? 
N1 N2 C3 C18 -179.79(13) . . . . ? 
N2 C3 C4 C5 -0.25(19) . . . . ? 
C18 C3 C4 C5 179.69(15) . . . . ? 
N2 N1 C5 C4 -0.15(17) . . . . ? 
C12 N1 C5 C4 -178.05(14) . . . . ? 
N2 N1 C5 C6 -178.78(14) . . . . ? 
C12 N1 C5 C6 3.3(2) . . . . ? 
C3 C4 C5 N1 0.23(17) . . . . ? 
C3 C4 C5 C6 178.76(15) . . . . ? 
N1 C5 C6 C11 -141.98(16) . . . . ? 
C4 C5 C6 C11 39.7(2) . . . . ? 
N1 C5 C6 C7 40.0(2) . . . . ? 
C4 C5 C6 C7 -138.29(17) . . . . ? 
C11 C6 C7 C8 -0.4(2) . . . . ? 
C5 C6 C7 C8 177.72(15) . . . . ? 
C6 C7 C8 N9 0.9(3) . . . . ? 
C7 C8 N9 C10 -1.0(3) . . . . ? 
C8 N9 C10 C11 0.5(3) . . . . ? 
N9 C10 C11 C6 0.0(3) . . . . ? 
C7 C6 C11 C10 0.0(2) . . . . ? 
C5 C6 C11 C10 -178.20(16) . . . . ? 
N2 N1 C12 C17 -119.50(16) . . . . ? 
C5 N1 C12 C17 58.3(2) . . . . ? 
N2 N1 C12 C13 61.52(19) . . . . ? 
C5 N1 C12 C13 -120.70(18) . . . . ? 
C17 C12 C13 C14 -1.9(2) . . . . ? 
N1 C12 C13 C14 177.03(14) . . . . ? 
C12 C13 C14 C15 -0.2(3) . . . . ? 
C13 C14 C15 C16 2.0(3) . . . . ? 
C14 C15 C16 C17 -1.7(3) . . . . ? 
C15 C16 C17 C12 -0.4(3) . . . . ? 
C13 C12 C17 C16 2.2(2) . . . . ? 
N1 C12 C17 C16 -176.74(14) . . . . ? 
N2 C3 C18 C19 161.19(15) . . . . ? 
C4 C3 C18 C19 -18.7(3) . . . . ? 
N2 C3 C18 C23 -18.9(2) . . . . ? 
C4 C3 C18 C23 161.20(17) . . . . ? 
C23 C18 C19 C20 -0.2(3) . . . . ? 
C3 C18 C19 C20 179.73(17) . . . . ? 
C18 C19 C20 C21 -0.1(3) . . . . ? 
C19 C20 C21 C22 0.5(3) . . . . ? 
C20 C21 C22 C23 -0.6(3) . . . . ? 
C21 C22 C23 C18 0.3(3) . . . . ? 
C19 C18 C23 C22 0.1(3) . . . . ? 
C3 C18 C23 C22 -179.85(16) . . . . ? 
 
_diffrn_measured_fraction_theta_max    0.932 
_diffrn_reflns_theta_full              25.02 
_diffrn_measured_fraction_theta_full   0.932 
_refine_diff_density_max    0.127 
_refine_diff_density_min   -0.144 
_refine_diff_density_rms    0.027 
 -0.2(3) . . . . ? 
C3 C18 C19 C20 179.73(17) . . . . ? 
C18 C19 C20 C21 -0.1(3) . . . . ? 
C19 C20 C21 C22 0.5(3) . . . . ? 
C20 C21 C22 C23 -0.6(3) . . . . ? 
C21 C22 C23 C18 0.3(3) . . . . ? 
C19 C18 C23 C22 0.1(3) . . . . ? 
C3 C18 C23 C22 -179.85(16) . . . . ? 
 
_diffrn_measured_fraction_theta_max    0.932 
_diffrn_reflns_theta_