data_fct916m 
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C22 H18 N2' 
_chemical_formula_weight          310.38 
 
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    'P21/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                    9.7088(13) 
_cell_length_b                    11.3662(15) 
_cell_length_c                    14.8567(19) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  97.069(2) 
_cell_angle_gamma                 90.00 
_cell_volume                      1627.0(4) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     150(2) 
_cell_measurement_reflns_used     4105 
_cell_measurement_theta_min        2.26
_cell_measurement_theta_max       28.15
 
_exptl_crystal_description        'PLATES'
_exptl_crystal_colour             'PALE YELLOW' 
_exptl_crystal_size_max           0.48 
_exptl_crystal_size_mid           0.33 
_exptl_crystal_size_min           0.14 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.267 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              656 
_exptl_absorpt_coefficient_mu     0.075 
_exptl_absorpt_correction_type    'MULTI-SCAN'
_exptl_absorpt_correction_T_min   0.9651 
_exptl_absorpt_correction_T_max   0.9896 
_exptl_absorpt_process_details    'BRUKER SADABS' 
 
_exptl_special_details 
; 
 ? 
; 
 
_diffrn_ambient_temperature       150(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   'BRUKER SMART APEX CCD DIFFARCTOMETER' 
_diffrn_measurement_method        'OMEGA-PHI SCAN' 
_diffrn_detector_area_resol_mean  ? 
_diffrn_standards_number          ? 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         ? 
_diffrn_reflns_number             8645 
_diffrn_reflns_av_R_equivalents   0.0765 
_diffrn_reflns_av_sigmaI/netI     0.0539 
_diffrn_reflns_limit_h_min        -11 
_diffrn_reflns_limit_h_max        11 
_diffrn_reflns_limit_k_min        -12 
_diffrn_reflns_limit_k_max        14 
_diffrn_reflns_limit_l_min        -12 
_diffrn_reflns_limit_l_max        18 
_diffrn_reflns_theta_min          2.26 
_diffrn_reflns_theta_max          26.00 
_reflns_number_total              3178 
_reflns_number_gt                 2640 
_reflns_threshold_expression      >2sigma(I) 
 
_computing_data_collection        'BRUKER SMART' 
_computing_cell_refinement        'BRUKER SMART' 
_computing_data_reduction         'BRUKER SAINT' 
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)' 
_computing_molecular_graphics     'ORTEP' 
_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^)+(0.0555P)^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          3178 
_refine_ls_number_parameters      289 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0461 
_refine_ls_R_factor_gt            0.0386 
_refine_ls_wR_factor_ref          0.1026 
_refine_ls_wR_factor_gt           0.0989 
_refine_ls_goodness_of_fit_ref    1.046 
_refine_ls_restrained_S_all       1.046 
_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 0.96001(9) 0.35581(8) 0.05693(6) 0.0232(2) Uani 1 1 d . . . 
N2 N 0.97492(9) 0.49824(8) 0.16016(6) 0.0234(2) Uani 1 1 d . . . 
C10 C 0.74135(11) 0.58994(10) 0.12774(8) 0.0231(3) Uani 1 1 d . . . 
C18 C 1.27913(12) 0.48102(10) 0.17442(7) 0.0243(3) Uani 1 1 d . . . 
C6 C 0.89862(12) 0.15865(9) -0.00520(7) 0.0240(3) Uani 1 1 d . . . 
C15 C 0.63385(12) 0.62119(10) 0.06071(8) 0.0275(3) Uani 1 1 d . . . 
C9 C 0.84469(11) 0.50042(9) 0.11095(7) 0.0220(3) Uani 1 1 d . . . 
C17 C 1.18958(11) 0.38528(10) 0.15544(7) 0.0233(3) Uani 1 1 d . . . 
C16 C 1.04234(11) 0.41060(9) 0.12581(7) 0.0221(3) Uani 1 1 d . . . 
C19 C 1.41962(12) 0.46355(11) 0.20000(8) 0.0280(3) Uani 1 1 d . . . 
C11 C 0.75215(12) 0.64855(10) 0.21101(8) 0.0276(3) Uani 1 1 d . . . 
C1 C 0.81179(13) 0.12740(10) -0.08249(8) 0.0286(3) Uani 1 1 d . . . 
C5 C 0.89528(14) 0.09150(11) 0.07299(8) 0.0334(3) Uani 1 1 d . . . 
C14 C 0.53978(13) 0.70848(11) 0.07672(9) 0.0317(3) Uani 1 1 d . . . 
C7 C 0.99439(12) 0.26292(10) -0.00616(8) 0.0255(3) Uani 1 1 d . . . 
C20 C 1.47303(13) 0.35029(11) 0.20769(8) 0.0325(3) Uani 1 1 d . . . 
C8 C 0.83464(12) 0.41307(10) 0.04762(8) 0.0238(3) Uani 1 1 d . . . 
C12 C 0.65867(13) 0.73666(11) 0.22626(9) 0.0318(3) Uani 1 1 d . . . 
C13 C 0.55235(13) 0.76651(11) 0.15947(9) 0.0333(3) Uani 1 1 d . . . 
C21 C 1.38506(13) 0.25466(11) 0.19230(9) 0.0330(3) Uani 1 1 d . . . 
C22 C 1.24399(12) 0.27173(10) 0.16616(8) 0.0284(3) Uani 1 1 d . . . 
C3 C 0.71938(14) -0.03289(11) -0.00378(10) 0.0367(3) Uani 1 1 d . . . 
C2 C 0.72331(14) 0.03155(11) -0.08221(9) 0.0337(3) Uani 1 1 d . . . 
C4 C 0.80579(16) -0.00287(12) 0.07348(10) 0.0401(3) Uani 1 1 d . . . 
H18 H 1.2402(12) 0.5610(11) 0.1678(8) 0.022(3) Uiso 1 1 d . . . 
H7B H 1.0951(13) 0.2418(10) 0.0129(8) 0.026(3) Uiso 1 1 d . . . 
H15 H 0.6252(13) 0.5808(12) 0.0006(9) 0.037(4) Uiso 1 1 d . . . 
H14 H 0.4666(14) 0.7300(11) 0.0279(9) 0.035(3) Uiso 1 1 d . . . 
H19 H 1.4814(13) 0.5313(11) 0.2115(8) 0.028(3) Uiso 1 1 d . . . 
H22 H 1.1820(14) 0.2049(12) 0.1537(9) 0.035(3) Uiso 1 1 d . . . 
H11 H 0.8270(13) 0.6263(10) 0.2577(8) 0.024(3) Uiso 1 1 d . . . 
H1 H 0.8124(13) 0.1751(12) -0.1380(9) 0.032(3) Uiso 1 1 d . . . 
H7A H 0.9834(13) 0.2979(10) -0.0685(9) 0.027(3) Uiso 1 1 d . . . 
H20 H 1.5731(15) 0.3361(12) 0.2281(9) 0.040(4) Uiso 1 1 d . . . 
H3 H 0.6561(15) -0.0997(14) -0.0050(9) 0.045(4) Uiso 1 1 d . . . 
H12 H 0.6677(15) 0.7776(13) 0.2850(10) 0.049(4) Uiso 1 1 d . . . 
H21 H 1.4226(15) 0.1733(13) 0.2018(9) 0.042(4) Uiso 1 1 d . . . 
H5 H 0.9611(14) 0.1119(11) 0.1263(10) 0.040(4) Uiso 1 1 d . . . 
H13 H 0.4874(15) 0.8299(13) 0.1678(9) 0.044(4) Uiso 1 1 d . . . 
H2 H 0.6610(14) 0.0138(12) -0.1390(9) 0.038(4) Uiso 1 1 d . . . 
H4 H 0.8036(16) -0.0495(14) 0.1276(11) 0.057(4) Uiso 1 1 d . . . 
H8 H 0.7609(13) 0.3897(11) 0.0029(8) 0.029(3) 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 
N1 0.0212(5) 0.0201(5) 0.0286(5) -0.0020(4) 0.0044(4) -0.0009(4) 
N2 0.0209(5) 0.0203(5) 0.0296(5) -0.0004(4) 0.0056(4) -0.0005(4) 
C10 0.0187(6) 0.0191(5) 0.0326(6) 0.0013(4) 0.0074(4) -0.0029(4) 
C18 0.0260(6) 0.0224(6) 0.0249(6) 0.0004(5) 0.0040(5) -0.0002(5) 
C6 0.0237(6) 0.0197(6) 0.0295(6) -0.0024(5) 0.0068(5) 0.0016(4) 
C15 0.0249(6) 0.0267(6) 0.0316(6) 0.0023(5) 0.0059(5) -0.0014(5) 
C9 0.0197(6) 0.0195(5) 0.0271(6) 0.0026(4) 0.0048(4) -0.0023(4) 
C17 0.0216(6) 0.0245(6) 0.0243(5) -0.0011(5) 0.0049(4) 0.0004(4) 
C16 0.0219(6) 0.0187(5) 0.0264(6) 0.0012(4) 0.0051(4) -0.0032(4) 
C19 0.0249(6) 0.0288(7) 0.0300(6) -0.0020(5) 0.0022(5) -0.0053(5) 
C11 0.0202(6) 0.0262(6) 0.0364(7) -0.0018(5) 0.0041(5) -0.0028(5) 
C1 0.0312(7) 0.0227(6) 0.0317(6) -0.0001(5) 0.0034(5) 0.0009(5) 
C5 0.0404(8) 0.0298(7) 0.0293(6) 0.0002(5) 0.0018(6) -0.0042(6) 
C14 0.0231(6) 0.0301(7) 0.0424(7) 0.0089(6) 0.0055(5) 0.0032(5) 
C7 0.0262(6) 0.0233(6) 0.0279(6) -0.0040(5) 0.0061(5) -0.0008(5) 
C20 0.0216(6) 0.0358(7) 0.0389(7) -0.0024(6) -0.0001(5) 0.0026(5) 
C8 0.0205(6) 0.0221(6) 0.0284(6) 0.0005(5) 0.0017(5) -0.0009(5) 
C12 0.0275(6) 0.0268(6) 0.0425(7) -0.0074(6) 0.0104(5) -0.0029(5) 
C13 0.0273(7) 0.0244(6) 0.0500(8) 0.0003(6) 0.0126(6) 0.0029(5) 
C21 0.0287(7) 0.0257(7) 0.0433(7) -0.0029(6) -0.0004(5) 0.0053(5) 
C22 0.0262(6) 0.0217(6) 0.0367(7) -0.0015(5) 0.0021(5) -0.0012(5) 
C3 0.0362(8) 0.0222(6) 0.0532(8) -0.0025(6) 0.0114(6) -0.0058(5) 
C2 0.0315(7) 0.0254(7) 0.0425(8) -0.0057(6) -0.0018(6) -0.0016(5) 
C4 0.0530(9) 0.0296(7) 0.0396(7) 0.0055(6) 0.0129(7) -0.0063(6) 
 
_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 C16 1.3685(14) . ? 
N1 C8 1.3722(14) . ? 
N1 C7 1.4770(14) . ? 
N2 C16 1.3280(14) . ? 
N2 C9 1.3806(14) . ? 
C10 C15 1.3969(16) . ? 
C10 C11 1.3976(16) . ? 
C10 C9 1.4717(15) . ? 
C18 C19 1.3844(16) . ? 
C18 C17 1.3997(15) . ? 
C18 H18 0.985(12) . ? 
C6 C1 1.3847(17) . ? 
C6 C5 1.3936(17) . ? 
C6 C7 1.5076(16) . ? 
C15 C14 1.3887(16) . ? 
C15 H15 0.998(13) . ? 
C9 C8 1.3631(16) . ? 
C17 C22 1.3962(15) . ? 
C17 C16 1.4714(15) . ? 
C19 C20 1.3873(17) . ? 
C19 H19 0.979(12) . ? 
C11 C12 1.3887(16) . ? 
C11 H11 0.974(12) . ? 
C1 C2 1.3878(17) . ? 
C1 H1 0.988(13) . ? 
C5 C4 1.3810(18) . ? 
C5 H5 0.982(14) . ? 
C14 C13 1.3872(18) . ? 
C14 H14 0.982(14) . ? 
C7 H7B 1.013(12) . ? 
C7 H7A 1.002(12) . ? 
C20 C21 1.3838(18) . ? 
C20 H20 0.994(14) . ? 
C8 H8 0.953(13) . ? 
C12 C13 1.3832(18) . ? 
C12 H12 0.983(15) . ? 
C13 H13 0.975(14) . ? 
C21 C22 1.3905(17) . ? 
C21 H21 0.998(14) . ? 
C22 H22 0.973(13) . ? 
C3 C4 1.379(2) . ? 
C3 C2 1.3808(19) . ? 
C3 H3 0.976(15) . ? 
C2 H2 0.996(14) . ? 
C4 H4 0.965(16) . ? 
 
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 
C16 N1 C8 106.79(9) . . ? 
C16 N1 C7 130.02(10) . . ? 
C8 N1 C7 122.82(10) . . ? 
C16 N2 C9 105.82(9) . . ? 
C15 C10 C11 118.55(10) . . ? 
C15 C10 C9 121.34(10) . . ? 
C11 C10 C9 120.08(10) . . ? 
C19 C18 C17 120.69(11) . . ? 
C19 C18 H18 120.9(7) . . ? 
C17 C18 H18 118.4(7) . . ? 
C1 C6 C5 118.46(11) . . ? 
C1 C6 C7 120.46(10) . . ? 
C5 C6 C7 121.07(11) . . ? 
C14 C15 C10 120.60(11) . . ? 
C14 C15 H15 119.8(8) . . ? 
C10 C15 H15 119.6(8) . . ? 
C8 C9 N2 109.61(10) . . ? 
C8 C9 C10 128.92(11) . . ? 
N2 C9 C10 121.44(10) . . ? 
C22 C17 C18 118.60(11) . . ? 
C22 C17 C16 123.70(10) . . ? 
C18 C17 C16 117.69(10) . . ? 
N2 C16 N1 111.01(10) . . ? 
N2 C16 C17 122.58(10) . . ? 
N1 C16 C17 126.25(10) . . ? 
C18 C19 C20 120.09(11) . . ? 
C18 C19 H19 119.8(7) . . ? 
C20 C19 H19 120.1(7) . . ? 
C12 C11 C10 120.58(11) . . ? 
C12 C11 H11 121.1(7) . . ? 
C10 C11 H11 118.3(7) . . ? 
C6 C1 C2 120.85(11) . . ? 
C6 C1 H1 119.1(7) . . ? 
C2 C1 H1 120.0(7) . . ? 
C4 C5 C6 120.59(12) . . ? 
C4 C5 H5 121.8(8) . . ? 
C6 C5 H5 117.6(8) . . ? 
C13 C14 C15 120.23(12) . . ? 
C13 C14 H14 120.8(8) . . ? 
C15 C14 H14 118.9(8) . . ? 
N1 C7 C6 111.60(9) . . ? 
N1 C7 H7B 106.1(7) . . ? 
C6 C7 H7B 112.7(7) . . ? 
N1 C7 H7A 107.3(7) . . ? 
C6 C7 H7A 109.0(7) . . ? 
H7B C7 H7A 110.0(9) . . ? 
C21 C20 C19 119.89(11) . . ? 
C21 C20 H20 118.9(8) . . ? 
C19 C20 H20 121.1(8) . . ? 
C9 C8 N1 106.78(10) . . ? 
C9 C8 H8 131.9(7) . . ? 
N1 C8 H8 121.3(7) . . ? 
C13 C12 C11 120.33(12) . . ? 
C13 C12 H12 119.8(9) . . ? 
C11 C12 H12 119.8(9) . . ? 
C12 C13 C14 119.71(11) . . ? 
C12 C13 H13 121.8(8) . . ? 
C14 C13 H13 118.4(8) . . ? 
C20 C21 C22 120.22(12) . . ? 
C20 C21 H21 119.8(8) . . ? 
C22 C21 H21 119.9(8) . . ? 
C21 C22 C17 120.44(11) . . ? 
C21 C22 H22 120.6(8) . . ? 
C17 C22 H22 118.9(8) . . ? 
C4 C3 C2 119.61(12) . . ? 
C4 C3 H3 121.7(8) . . ? 
C2 C3 H3 118.7(8) . . ? 
C3 C2 C1 120.02(12) . . ? 
C3 C2 H2 122.0(8) . . ? 
C1 C2 H2 117.9(8) . . ? 
C3 C4 C5 120.44(12) . . ? 
C3 C4 H4 119.0(10) . . ? 
C5 C4 H4 120.6(10) . . ? 
 
_diffrn_measured_fraction_theta_max    0.995 
_diffrn_reflns_theta_full              26.00 
_diffrn_measured_fraction_theta_full   0.995 
_refine_diff_density_max    0.219 
_refine_diff_density_min   -0.143 
_refine_diff_density_rms    0.041