data_nf-1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H10 N2' _chemical_formula_sum 'C13 H10 N2' _chemical_formula_weight 194.23 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 'C c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 5.9752(9) _cell_length_b 25.124(4) _cell_length_c 13.8320(17) _cell_angle_alpha 90.00 _cell_angle_beta 97.080(9) _cell_angle_gamma 90.00 _cell_volume 2060.6(5) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 1.35 _cell_measurement_theta_max 22.35 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.252 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 816.0 _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_correction_T_min 0.961 _exptl_absorpt_correction_T_max 0.979 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12127 _diffrn_reflns_av_R_equivalents 0.0269 _diffrn_reflns_av_sigmaI/netI 0.0428 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -33 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.62 _diffrn_reflns_theta_max 28.39 _reflns_number_total 5146 _reflns_number_gt 2204 _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 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.1500P)^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 ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 1(4) _refine_ls_number_reflns 4329 _refine_ls_number_parameters 275 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.1370 _refine_ls_R_factor_gt 0.0681 _refine_ls_wR_factor_ref 0.2543 _refine_ls_wR_factor_gt 0.2066 _refine_ls_goodness_of_fit_ref 1.009 _refine_ls_restrained_S_all 1.023 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.001 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 C8 C 0.3227(8) 0.49737(18) 0.2396(3) 0.0707(11) Uani 1 1 d . . . C5 C 0.0788(8) 0.40517(19) 0.3852(3) 0.0748(12) Uani 1 1 d . . . C7 C 0.3841(8) 0.4068(2) 0.3086(4) 0.0786(13) Uani 1 1 d . . . H7 H 0.5169 0.3985 0.2833 0.094 Uiso 1 1 calc R . . C6 C 0.2671(8) 0.37489(18) 0.3681(3) 0.0743(12) Uani 1 1 d . . . C13 C 0.1813(10) 0.5404(2) 0.2336(4) 0.0905(14) Uani 1 1 d . . . H13 H 0.0532 0.5408 0.2656 0.109 Uiso 1 1 calc R . . C9 C 0.5126(11) 0.4974(2) 0.1949(4) 0.0935(16) Uani 1 1 d . . . H9 H 0.6109 0.4686 0.2021 0.112 Uiso 1 1 calc R . . C10 C 0.5581(12) 0.5394(2) 0.1402(5) 0.1075(18) Uani 1 1 d . . . H10 H 0.6848 0.5388 0.1073 0.129 Uiso 1 1 calc R . . C12 C 0.2356(14) 0.5829(2) 0.1786(5) 0.110(2) Uani 1 1 d . . . H12 H 0.1415 0.6125 0.1732 0.132 Uiso 1 1 calc R . . C1 C 0.2952(10) 0.3229(2) 0.4096(4) 0.0871(15) Uani 1 1 d . . . H1 H 0.4184 0.3020 0.3995 0.105 Uiso 1 1 calc R . . C2 C 0.1381(11) 0.3051(2) 0.4640(4) 0.0943(16) Uani 1 1 d . . . H2 H 0.1542 0.2713 0.4915 0.113 Uiso 1 1 calc R . . C11 C 0.4207(13) 0.5830(2) 0.1323(4) 0.1041(18) Uani 1 1 d . . . H11 H 0.4545 0.6123 0.0955 0.125 Uiso 1 1 calc R . . C3 C -0.0500(11) 0.3363(3) 0.4803(4) 0.1005(17) Uani 1 1 d . . . H3 H -0.1538 0.3227 0.5187 0.121 Uiso 1 1 calc R . . C4 C -0.0832(9) 0.3852(2) 0.4421(4) 0.0933(15) Uani 1 1 d . . . H4 H -0.2088 0.4052 0.4526 0.112 Uiso 1 1 calc R . . N1 N 0.2667(6) 0.45113(14) 0.2959(3) 0.0678(10) Uani 1 1 d . . . N2 N 0.0766(6) 0.45345(16) 0.3400(3) 0.0811(11) Uani 1 1 d . . . C15 C 0.1974(12) 0.13694(19) 0.5804(4) 0.0884(15) Uani 1 1 d . . . C16 C 0.4004(11) 0.1153(2) 0.5990(4) 0.0950(17) Uani 1 1 d . . . H16 H 0.5035 0.1287 0.6490 0.114 Uiso 1 1 calc R . . C17 C 0.4583(11) 0.0724(3) 0.5432(6) 0.112(2) Uani 1 1 d . . . H17 H 0.5993 0.0563 0.5551 0.134 Uiso 1 1 calc R . . C14 C 0.0491(11) 0.1185(3) 0.5124(6) 0.109(2) Uani 1 1 d . . . H14 H -0.0919 0.1347 0.5028 0.131 Uiso 1 1 calc R . . C18 C 0.2951(17) 0.0542(2) 0.4682(5) 0.114(2) Uani 1 1 d . . . H18 H 0.3268 0.0265 0.4275 0.137 Uiso 1 1 calc R . . C19 C 0.0873(13) 0.0787(3) 0.4569(4) 0.111(2) Uani 1 1 d . . . H19 H -0.0256 0.0667 0.4096 0.133 Uiso 1 1 calc R . . N5 N -0.0627(8) 0.2045(2) 0.6237(4) 0.1196(19) Uani 1 1 d . . . C26 C -0.0561(12) 0.2436(2) 0.6956(4) 0.099(2) Uani 1 1 d . . . C22 C -0.0033(16) 0.3156(2) 0.8412(6) 0.115(2) Uani 1 1 d . . . H22 H 0.0109 0.3406 0.8910 0.138 Uiso 1 1 calc R . . C21 C -0.1887(13) 0.3142(3) 0.7841(6) 0.107(2) Uani 1 1 d . . . H21 H -0.2989 0.3386 0.7961 0.129 Uiso 1 1 calc R . . C24 C 0.1478(9) 0.2464(2) 0.7587(4) 0.0883(15) Uani 1 1 d . . . C20 C -0.2398(10) 0.2811(3) 0.7089(5) 0.109(2) Uani 1 1 d . . . H20 H -0.3771 0.2817 0.6690 0.131 Uiso 1 1 calc R . . C23 C 0.1678(13) 0.2839(3) 0.8338(5) 0.121(2) Uani 1 1 d . . . H23 H 0.2990 0.2863 0.8774 0.146 Uiso 1 1 calc R . . N3 N 0.1368(6) 0.18442(13) 0.6454(3) 0.0691(10) Uani 1 1 d . . . C27 C 0.2733(10) 0.2036(3) 0.7205(5) 0.1014(19) Uani 1 1 d D . . H28 H 0.28(2) 0.169(3) 0.664(9) 0.02(6) Uiso 1 1 d 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 C8 0.075(3) 0.076(3) 0.059(2) -0.006(2) 0.000(2) 0.003(2) C5 0.070(3) 0.090(3) 0.062(3) -0.006(2) -0.001(2) 0.002(2) C7 0.063(3) 0.099(3) 0.077(3) -0.008(3) 0.019(2) 0.010(2) C6 0.067(3) 0.090(3) 0.064(3) -0.011(2) 0.002(2) 0.001(2) C13 0.090(3) 0.102(4) 0.080(3) 0.007(3) 0.015(3) 0.018(3) C9 0.102(4) 0.075(3) 0.106(4) 0.010(3) 0.024(4) 0.017(3) C10 0.102(4) 0.107(4) 0.119(4) 0.007(4) 0.036(4) 0.005(3) C12 0.149(6) 0.085(4) 0.094(4) 0.000(3) 0.006(4) 0.033(4) C1 0.096(4) 0.087(3) 0.077(3) -0.009(3) 0.006(3) 0.008(3) C2 0.113(5) 0.082(3) 0.085(3) 0.005(3) 0.003(3) -0.013(3) C11 0.132(5) 0.100(4) 0.080(4) 0.008(3) 0.010(4) -0.004(4) C3 0.095(4) 0.120(4) 0.090(4) 0.004(4) 0.026(3) -0.032(4) C4 0.082(3) 0.123(5) 0.076(3) -0.010(3) 0.013(3) 0.003(3) N1 0.057(2) 0.079(2) 0.067(2) -0.0140(17) 0.0083(17) 0.0136(17) N2 0.066(2) 0.099(3) 0.079(2) -0.014(2) 0.014(2) 0.016(2) C15 0.112(5) 0.066(3) 0.094(4) 0.014(3) 0.039(4) -0.004(3) C16 0.094(4) 0.112(4) 0.076(3) -0.008(3) -0.005(3) -0.028(4) C17 0.081(4) 0.119(5) 0.138(6) 0.052(4) 0.028(4) 0.036(3) C14 0.079(3) 0.115(5) 0.128(5) 0.022(4) -0.002(4) 0.003(3) C18 0.182(8) 0.072(3) 0.100(4) -0.011(3) 0.070(6) 0.002(4) C19 0.122(5) 0.127(5) 0.080(4) -0.031(4) -0.004(4) -0.028(4) N5 0.073(3) 0.162(5) 0.121(4) 0.062(4) 0.000(3) -0.016(3) C26 0.166(7) 0.068(3) 0.068(3) -0.008(3) 0.034(4) -0.048(4) C22 0.127(6) 0.091(4) 0.127(5) -0.002(3) 0.017(5) 0.010(4) C21 0.102(5) 0.092(4) 0.135(6) 0.008(4) 0.040(5) 0.011(3) C24 0.084(3) 0.077(3) 0.109(4) 0.014(3) 0.035(3) 0.003(3) C20 0.082(4) 0.121(5) 0.124(5) 0.041(4) 0.016(4) -0.011(4) C23 0.127(6) 0.107(5) 0.125(5) 0.013(4) -0.002(4) -0.044(5) N3 0.059(2) 0.077(2) 0.069(2) 0.0083(17) -0.0005(18) -0.0099(18) C27 0.086(4) 0.119(5) 0.099(4) 0.007(4) 0.009(3) -0.016(3) _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 C8 C9 1.357(8) . ? C8 C13 1.368(7) . ? C8 N1 1.460(6) . ? C5 N2 1.364(6) . ? C5 C6 1.402(6) . ? C5 C4 1.413(8) . ? C7 N1 1.316(6) . ? C7 C6 1.397(7) . ? C6 C1 1.428(7) . ? C13 C12 1.374(9) . ? C9 C10 1.346(8) . ? C10 C11 1.365(9) . ? C12 C11 1.345(10) . ? C1 C2 1.351(8) . ? C2 C3 1.412(9) . ? C3 C4 1.341(8) . ? N1 N2 1.356(5) . ? C15 C14 1.296(9) . ? C15 C16 1.325(9) . ? C15 N3 1.563(7) . ? C16 C17 1.396(9) . ? C17 C18 1.410(11) . ? C14 C19 1.299(9) . ? C18 C19 1.377(10) . ? N5 N3 1.295(6) . ? N5 C26 1.394(8) . ? C26 C24 1.411(8) . ? C26 C20 1.475(9) . ? C22 C21 1.279(10) . ? C22 C23 1.309(11) . ? C21 C20 1.337(10) . ? C24 C23 1.398(9) . ? C24 C27 1.446(9) . ? N3 C27 1.330(7) . ? 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 C9 C8 C13 121.1(5) . . ? C9 C8 N1 120.2(4) . . ? C13 C8 N1 118.7(5) . . ? N2 C5 C6 111.6(4) . . ? N2 C5 C4 127.1(5) . . ? C6 C5 C4 121.3(5) . . ? N1 C7 C6 105.5(4) . . ? C7 C6 C5 105.0(4) . . ? C7 C6 C1 136.0(5) . . ? C5 C6 C1 119.0(5) . . ? C12 C13 C8 117.5(6) . . ? C10 C9 C8 119.7(5) . . ? C9 C10 C11 120.8(7) . . ? C11 C12 C13 122.0(5) . . ? C2 C1 C6 118.2(5) . . ? C1 C2 C3 121.7(5) . . ? C12 C11 C10 118.9(6) . . ? C4 C3 C2 121.9(5) . . ? C3 C4 C5 117.8(5) . . ? C7 N1 N2 116.0(4) . . ? C7 N1 C8 126.2(4) . . ? N2 N1 C8 117.8(3) . . ? C5 N2 N1 101.9(3) . . ? C14 C15 C16 121.5(6) . . ? C14 C15 N3 120.2(6) . . ? C16 C15 N3 118.2(6) . . ? C15 C16 C17 119.5(5) . . ? C16 C17 C18 117.5(5) . . ? C15 C14 C19 123.4(6) . . ? C19 C18 C17 118.1(5) . . ? C14 C19 C18 119.9(6) . . ? N3 N5 C26 99.5(5) . . ? N5 C26 C24 115.0(6) . . ? N5 C26 C20 125.7(7) . . ? C24 C26 C20 119.4(5) . . ? C21 C22 C23 124.1(7) . . ? C22 C21 C20 126.5(7) . . ? C23 C24 C26 118.8(6) . . ? C23 C24 C27 140.5(7) . . ? C26 C24 C27 100.7(5) . . ? C21 C20 C26 113.1(6) . . ? C22 C23 C24 118.2(7) . . ? C27 N3 N5 119.9(5) . . ? C27 N3 C15 124.2(5) . . ? N5 N3 C15 115.9(5) . . ? N3 C27 C24 105.0(5) . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 28.39 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.556 _refine_diff_density_min -0.156 _refine_diff_density_rms 0.039