 
data_herges85 
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C14 H14 N4' 
_chemical_formula_weight          238.29 
 
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 2/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' 
 '-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                    25.9277(15) 
_cell_length_b                    7.9561(6) 
_cell_length_c                    13.1658(7) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  120.280(6) 
_cell_angle_gamma                 90.00 
_cell_volume                      2345.4(3) 
_cell_formula_units_Z             8 
_cell_measurement_temperature     200(2) 
_cell_measurement_reflns_used     ? 
_cell_measurement_theta_min       ? 
_cell_measurement_theta_max       ? 
 
_exptl_crystal_description        block 
_exptl_crystal_colour             colorless 
_exptl_crystal_size_max           0.3 
_exptl_crystal_size_mid           0.2 
_exptl_crystal_size_min           0.2 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.350 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              1008 
_exptl_absorpt_coefficient_mu     0.085 
_exptl_absorpt_correction_type    none 
_exptl_absorpt_correction_T_min   ? 
_exptl_absorpt_correction_T_max   ? 
_exptl_absorpt_process_details    ? 
 
_exptl_special_details 
; 
 ? 
; 
 
_diffrn_ambient_temperature       200(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   'STOE IPDS-1' 
_diffrn_measurement_method        'Phi scans' 
_diffrn_detector_area_resol_mean  ? 
_diffrn_standards_number          0 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   0 
_diffrn_standards_decay_%         0 
_diffrn_reflns_number             6973 
_diffrn_reflns_av_R_equivalents   0.0491 
_diffrn_reflns_av_sigmaI/netI     0.0419 
_diffrn_reflns_limit_h_min        -32 
_diffrn_reflns_limit_h_max        32 
_diffrn_reflns_limit_k_min        -10 
_diffrn_reflns_limit_k_max        10 
_diffrn_reflns_limit_l_min        -16 
_diffrn_reflns_limit_l_max        15 
_diffrn_reflns_theta_min          2.99 
_diffrn_reflns_theta_max          27.00 
_reflns_number_total              2511 
_reflns_number_gt                 1959 
_reflns_threshold_expression      >2sigma(I) 
 
_computing_data_collection        'STOE IPDS-1 program package' 
_computing_cell_refinement        'STOE IPDS-1 program package' 
_computing_data_reduction         'STOE IPDS-1 program package' 
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)' 
_computing_molecular_graphics     ? 
_computing_publication_material   'XCIF in SHELXTL-PC' 
 
_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)+(0.0535P)²+0.6611P] where P=(Fo²+2Fc²)/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          2511 
_refine_ls_number_parameters      181 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0603 
_refine_ls_R_factor_gt            0.0410 
_refine_ls_wR_factor_ref          0.1039 
_refine_ls_wR_factor_gt           0.0962 
_refine_ls_goodness_of_fit_ref    1.038 
_refine_ls_restrained_S_all       1.038 
_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 0.09841(5) 0.32235(14) 0.43387(10) 0.0343(3) Uani 1 1 d . . . 
N2 N 0.05736(5) 0.42585(14) 0.40784(10) 0.0345(3) Uani 1 1 d . . . 
C1 C 0.07049(5) 0.59917(15) 0.44856(11) 0.0304(3) Uani 1 1 d . A . 
C2 C 0.05687(5) 0.64375(16) 0.53437(11) 0.0314(3) Uani 1 1 d . . . 
H2 H 0.0453 0.5594 0.5701 0.038 Uiso 1 1 calc R . . 
C3 C 0.05996(5) 0.81124(16) 0.56869(11) 0.0324(3) Uani 1 1 d . . . 
N3 N 0.05038(6) 0.85438(16) 0.66057(11) 0.0428(3) Uani 1 1 d . . . 
H1N3 H 0.0279 0.7791 0.6736 0.064 Uiso 1 1 d R . . 
H2N3 H 0.0352 0.9598 0.6524 0.064 Uiso 1 1 d R . . 
C4 C 0.07605(6) 0.93160(16) 0.51228(12) 0.0359(3) Uani 1 1 d . . . 
H4 H 0.0775 1.0469 0.5324 0.043 Uiso 1 1 calc R . . 
C5 C 0.08989(6) 0.88492(17) 0.42744(12) 0.0369(3) Uani 1 1 d . A . 
H5 H 0.1011 0.9695 0.3913 0.044 Uiso 1 1 calc R . . 
C6 C 0.08793(6) 0.71765(16) 0.39305(12) 0.0346(3) Uani 1 1 d . . . 
C7 C 0.1086(4) 0.6787(13) 0.3086(9) 0.0426(17) Uani 0.55 1 d P A 1 
H7A H 0.1299 0.7793 0.3041 0.051 Uiso 0.55 1 calc PR A 1 
H7B H 0.0726 0.6645 0.2301 0.051 Uiso 0.55 1 calc PR A 1 
C8 C 0.1498(5) 0.5241(9) 0.3296(9) 0.0403(13) Uani 0.55 1 d P A 1 
H8A H 0.1247 0.4270 0.2851 0.048 Uiso 0.55 1 calc PR A 1 
H8B H 0.1766 0.5499 0.2984 0.048 Uiso 0.55 1 calc PR A 1 
C7' C 0.0955(5) 0.6533(15) 0.2902(10) 0.0358(17) Uani 0.45 1 d P A 2 
H7C H 0.0642 0.5690 0.2441 0.043 Uiso 0.45 1 calc PR A 2 
H7D H 0.0907 0.7481 0.2375 0.043 Uiso 0.45 1 calc PR A 2 
C8' C 0.1575(5) 0.5735(11) 0.3378(10) 0.0400(16) Uani 0.45 1 d P A 2 
H8C H 0.1852 0.6645 0.3454 0.048 Uiso 0.45 1 calc PR A 2 
H8D H 0.1548 0.4954 0.2769 0.048 Uiso 0.45 1 calc PR A 2 
C9 C 0.18713(6) 0.47594(17) 0.45654(12) 0.0345(3) Uani 1 1 d . . . 
C10 C 0.24868(6) 0.49755(17) 0.52715(13) 0.0377(3) Uani 1 1 d . A . 
H10 H 0.2690 0.5634 0.4980 0.045 Uiso 1 1 calc R . . 
C11 C 0.28151(6) 0.42685(17) 0.63814(13) 0.0376(3) Uani 1 1 d . . . 
H11 H 0.3233 0.4464 0.6834 0.045 Uiso 1 1 calc R A . 
C12 C 0.25362(6) 0.32669(16) 0.68423(12) 0.0337(3) Uani 1 1 d . A . 
N4 N 0.28468(6) 0.26219(18) 0.79700(12) 0.0495(3) Uani 1 1 d . . . 
H2N4 H 0.3251 0.2732 0.8343 0.074 Uiso 1 1 d R A . 
H1N4 H 0.2671 0.1761 0.8138 0.074 Uiso 1 1 d R . . 
C13 C 0.19249(6) 0.29755(15) 0.61340(12) 0.0321(3) Uani 1 1 d . . . 
H13 H 0.1727 0.2255 0.6404 0.038 Uiso 1 1 calc R A . 
C14 C 0.16031(6) 0.37343(15) 0.50340(11) 0.0304(3) Uani 1 1 d . A . 
 
 
_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 1.2492(16) . ? 
N1 C14 1.4482(16) . ? 
N2 C1 1.4563(16) . ? 
C1 C2 1.3890(19) . ? 
C1 C6 1.4002(18) . ? 
C2 C3 1.3964(19) . ? 
C3 N3 1.3949(18) . ? 
C3 C4 1.3982(19) . ? 
C4 C5 1.385(2) . ? 
C5 C6 1.3983(19) . ? 
C6 C7 1.491(12) . ? 
C6 C7' 1.549(12) . ? 
C7 C8 1.559(16) . ? 
C8 C9 1.498(11) . ? 
C7' C8' 1.537(19) . ? 
C8' C9 1.557(12) . ? 
C9 C10 1.395(2) . ? 
C9 C14 1.4007(18) . ? 
C10 C11 1.386(2) . ? 
C11 C12 1.4031(19) . ? 
C12 N4 1.3822(18) . ? 
C12 C13 1.3945(18) . ? 
C13 C14 1.3927(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 
N2 N1 C14 120.51(10) . . ? 
N1 N2 C1 120.97(10) . . ? 
C2 C1 C6 122.28(12) . . ? 
C2 C1 N2 115.67(11) . . ? 
C6 C1 N2 121.49(12) . . ? 
C1 C2 C3 120.68(12) . . ? 
N3 C3 C2 120.60(12) . . ? 
N3 C3 C4 121.56(12) . . ? 
C2 C3 C4 117.75(12) . . ? 
C5 C4 C3 120.84(12) . . ? 
C4 C5 C6 122.30(12) . . ? 
C5 C6 C1 116.12(12) . . ? 
C5 C6 C7 118.1(4) . . ? 
C1 C6 C7 125.6(4) . . ? 
C5 C6 C7' 126.7(5) . . ? 
C1 C6 C7' 116.7(5) . . ? 
C7 C6 C7' 13.6(6) . . ? 
C6 C7 C8 120.2(8) . . ? 
C9 C8 C7 113.5(7) . . ? 
C8' C7' C6 110.3(8) . . ? 
C7' C8' C9 120.0(9) . . ? 
C10 C9 C14 115.70(12) . . ? 
C10 C9 C8 126.2(4) . . ? 
C14 C9 C8 117.1(3) . . ? 
C10 C9 C8' 115.3(4) . . ? 
C14 C9 C8' 129.0(4) . . ? 
C8 C9 C8' 16.0(4) . . ? 
C11 C10 C9 122.72(12) . . ? 
C10 C11 C12 120.66(12) . . ? 
N4 C12 C13 120.45(12) . . ? 
N4 C12 C11 121.81(12) . . ? 
C13 C12 C11 117.71(12) . . ? 
C14 C13 C12 120.42(12) . . ? 
C13 C14 C9 122.69(12) . . ? 
C13 C14 N1 115.32(11) . . ? 
C9 C14 N1 121.54(12) . . ? 
 
_diffrn_measured_fraction_theta_max    0.978 
_diffrn_reflns_theta_full              27.00 
_diffrn_measured_fraction_theta_full   0.978 
_refine_diff_density_max    0.183 
_refine_diff_density_min   -0.204 
_refine_diff_density_rms    0.033 
