 
data_1
 
_audit_creation_method            'SHELXL-2014/7'
_shelx_SHELXL_version_number      '2014/7'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C19 H16 N4' 
_chemical_formula_weight          300.36

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'
 'N'  'N'   0.0061   0.0033
 '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'
 
_space_group_crystal_system       monoclinic
_space_group_IT_number            15
_space_group_name_H-M_alt         'C 2/c'
_space_group_name_Hall            '-C 2yc'
 
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
 
loop_
 _space_group_symop_operation_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                    23.9690(12)
_cell_length_b                    8.5622(4)
_cell_length_c                    19.4153(9)
_cell_angle_alpha                 90
_cell_angle_beta                  128.0550(10)
_cell_angle_gamma                 90
_cell_volume                      3137.5(3)
_cell_formula_units_Z             8
_cell_measurement_temperature     296(2)
_cell_measurement_reflns_used      6120
_cell_measurement_theta_min        2.61
_cell_measurement_theta_max       28.23
 
_exptl_crystal_description        cuboid
_exptl_crystal_colour             colourless
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.272          
_exptl_crystal_F_000              1264
_exptl_transmission_factor_min    0.985
_exptl_transmission_factor_max    0.992
_exptl_crystal_size_max           0.200
_exptl_crystal_size_mid           0.150
_exptl_crystal_size_min           0.100
_exptl_absorpt_coefficient_mu     0.078
_shelx_estimated_absorpt_T_min    ?
_shelx_estimated_absorpt_T_max    ?
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   ?
_exptl_absorpt_correction_T_max   ?
_exptl_absorpt_process_details    sadabs
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       296(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_source                    'fine-focus sealed tube'
_diffrn_measurement_device_type   'CCD area detector' 
_diffrn_measurement_method        'phi and omega scans' 
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             18694
_diffrn_reflns_av_unetI/netI      0.0198
_diffrn_reflns_av_R_equivalents   0.0233
_diffrn_reflns_limit_h_min        -31
_diffrn_reflns_limit_h_max        30
_diffrn_reflns_limit_k_min        -11
_diffrn_reflns_limit_k_max        11
_diffrn_reflns_limit_l_min        -25
_diffrn_reflns_limit_l_max        25
_diffrn_reflns_theta_min          2.158
_diffrn_reflns_theta_max          28.288
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.997
_diffrn_measured_fraction_theta_full  0.999
_diffrn_reflns_Laue_measured_fraction_max    0.997
_diffrn_reflns_Laue_measured_fraction_full   0.999
_diffrn_reflns_point_group_measured_fraction_max   0.997
_diffrn_reflns_point_group_measured_fraction_full  0.999
_reflns_number_total              3882
_reflns_number_gt                 2729
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .
 
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
 
_computing_data_collection        'Bruker SMART' 
_computing_cell_refinement        'Bruker SMART' 
_computing_data_reduction         'Bruker SHELXTL' 
_computing_structure_solution     'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement   'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics     'Bruker SHELXTL' 
_computing_publication_material   'Bruker SHELXTL'
_refine_special_details           ?
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1035P)²+3.1226P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_number_reflns          3882
_refine_ls_number_parameters      208
_refine_ls_number_restraints      29
_refine_ls_R_factor_all           0.1009
_refine_ls_R_factor_gt            0.0743
_refine_ls_wR_factor_ref          0.2205
_refine_ls_wR_factor_gt           0.2006
_refine_ls_goodness_of_fit_ref    1.042
_refine_ls_restrained_S_all       1.047
_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_site_symmetry_order  
 _atom_site_calc_flag
 _atom_site_refinement_flags_posn
 _atom_site_refinement_flags_adp
 _atom_site_refinement_flags_occupancy
 _atom_site_disorder_assembly
 _atom_site_disorder_group
N4 N 0.27460(9) 0.9977(2) 0.50473(12) 0.0550(5) Uani 1 1 d . . . . .
N1 N 0.37073(9) 0.8491(2) 0.55768(12) 0.0544(5) Uani 1 1 d . U . . .
N2 N 0.37031(9) 0.5610(2) 0.66872(12) 0.0592(6) Uani 1 1 d . . . . .
H2A H 0.3324 0.5388 0.6174 0.071 Uiso 1 1 calc R U . . .
N3 N 0.46569(9) 0.4849(2) 0.80672(12) 0.0526(5) Uani 1 1 d . . . . .
C15 C 0.40788(10) 0.4442(2) 0.72744(13) 0.0436(5) Uani 1 1 d . . . . .
C5 C 0.25023(12) 0.9411(3) 0.60670(16) 0.0565(6) Uani 1 1 d . U . . .
C9 C 0.32421(13) 0.9536(3) 0.49487(15) 0.0553(6) Uani 1 1 d . . . . .
C7 C 0.29286(12) 0.9170(2) 0.57570(14) 0.0529(6) Uani 1 1 d . U . . .
C14 C 0.39278(11) 0.7216(3) 0.69081(14) 0.0581(6) Uani 1 1 d . . . . .
H14A H 0.4426 0.7289 0.7169 0.070 Uiso 1 1 calc R U . . .
H14B H 0.3872 0.7571 0.7337 0.070 Uiso 1 1 calc R U . . .
C1 C 0.20411(14) 1.0723(3) 0.57618(17) 0.0630(6) Uani 1 1 d . . . . .
H1A H 0.2005 1.1425 0.5371 0.076 Uiso 1 1 calc R U . . .
C8 C 0.35068(11) 0.8254(3) 0.61175(14) 0.0552(6) Uani 1 1 d . U . . .
C16 C 0.38583(13) 0.2889(3) 0.70423(16) 0.0573(6) Uani 1 1 d . . . . .
H16A H 0.3452 0.2636 0.6486 0.069 Uiso 1 1 calc R U . . .
C6 C 0.25224(14) 0.8399(3) 0.66450(18) 0.0694(7) Uani 1 1 d . . . . .
H6A H 0.2814 0.7523 0.6853 0.083 Uiso 1 1 calc R U . . .
C10 C 0.33366(15) 0.9985(3) 0.43423(19) 0.0683(7) Uani 1 1 d . . . . .
H10A H 0.3024 1.0695 0.3907 0.082 Uiso 1 1 calc R U . . .
C13 C 0.42479(13) 0.7833(3) 0.56273(17) 0.0642(7) Uani 1 1 d . . . . .
H13A H 0.4542 0.7095 0.6056 0.077 Uiso 1 1 calc R U . . .
C19 C 0.50315(13) 0.3695(3) 0.86381(16) 0.0673(7) Uani 1 1 d . . . . .
H19A H 0.5441 0.3961 0.9189 0.081 Uiso 1 1 calc R U . . .
C18 C 0.48548(16) 0.2158(3) 0.8469(2) 0.0807(9) Uani 1 1 d . . . . .
H18A H 0.5132 0.1401 0.8893 0.097 Uiso 1 1 calc R U . . .
C17 C 0.42526(18) 0.1757(3) 0.7651(2) 0.0772(8) Uani 1 1 d . . . . .
H17A H 0.4116 0.0716 0.7515 0.093 Uiso 1 1 calc R U . . .
C2 C 0.16519(15) 1.0937(4) 0.6051(2) 0.0742(8) Uani 1 1 d . . . . .
H2B H 0.1350 1.1794 0.5852 0.089 Uiso 1 1 calc R U . . .
C11 C 0.38786(18) 0.9402(4) 0.4375(2) 0.0796(9) Uani 1 1 d . . . . .
H11A H 0.3944 0.9728 0.3972 0.096 Uiso 1 1 calc R U . . .
C12 C 0.43507(16) 0.8278(4) 0.5035(2) 0.0834(9) Uani 1 1 d . . . . .
H12A H 0.4721 0.7858 0.5060 0.100 Uiso 1 1 calc R U . . .
C4 C 0.21163(19) 0.8681(4) 0.6910(2) 0.0847(9) Uani 1 1 d . . . . .
H4A H 0.2136 0.7992 0.7295 0.102 Uiso 1 1 calc R U . . .
C3 C 0.1694(2) 0.9932(5) 0.6623(2) 0.0886(10) Uani 1 1 d . . . . .
H3B H 0.1427 1.0114 0.6815 0.106 Uiso 1 1 calc R U . . .
 
 
_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
N4 C7 1.350(3) . ?
N4 C9 1.369(3) . ?
N1 C13 1.360(3) . ?
N1 C9 1.362(3) . ?
N1 C8 1.413(3) . ?
N2 C15 1.359(3) . ?
N2 C14 1.442(3) . ?
N2 H2A 0.8600 . ?
N3 C15 1.335(3) . ?
N3 C19 1.336(3) . ?
C15 C16 1.399(3) . ?
C5 C6 1.395(4) . ?
C5 C1 1.424(4) . ?
C5 C7 1.486(4) . ?
C9 C10 1.383(4) . ?
C7 C8 1.353(3) . ?
C14 C8 1.501(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C1 C2 1.366(4) . ?
C1 H1A 0.9300 . ?
C16 C17 1.361(3) . ?
C16 H16A 0.9300 . ?
C6 C4 1.375(4) . ?
C6 H6A 0.9300 . ?
C10 C11 1.356(4) . ?
C10 H10A 0.9300 . ?
C13 C12 1.371(4) . ?
C13 H13A 0.9300 . ?
C19 C18 1.359(4) . ?
C19 H19A 0.9300 . ?
C18 C17 1.378(4) . ?
C18 H18A 0.9300 . ?
C17 H17A 0.9300 . ?
C2 C3 1.359(5) . ?
C2 H2B 0.9300 . ?
C11 C12 1.435(5) . ?
C11 H11A 0.9300 . ?
C12 H12A 0.9300 . ?
C4 C3 1.337(5) . ?
C4 H4A 0.9300 . ?
C3 H3B 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
C7 N4 C9 103.80(19) . . ?
C13 N1 C9 123.7(2) . . ?
C13 N1 C8 129.2(2) . . ?
C9 N1 C8 107.10(19) . . ?
C15 N2 C14 121.31(17) . . ?
C15 N2 H2A 119.3 . . ?
C14 N2 H2A 119.3 . . ?
C15 N3 C19 116.9(2) . . ?
N3 C15 N2 117.07(19) . . ?
N3 C15 C16 122.52(19) . . ?
N2 C15 C16 120.42(19) . . ?
C6 C5 C1 117.2(2) . . ?
C6 C5 C7 123.2(2) . . ?
C1 C5 C7 119.5(2) . . ?
N1 C9 N4 111.0(2) . . ?
N1 C9 C10 118.1(2) . . ?
N4 C9 C10 130.9(2) . . ?
N4 C7 C8 114.1(2) . . ?
N4 C7 C5 118.1(2) . . ?
C8 C7 C5 127.7(2) . . ?
N2 C14 C8 111.57(17) . . ?
N2 C14 H14A 109.3 . . ?
C8 C14 H14A 109.3 . . ?
N2 C14 H14B 109.3 . . ?
C8 C14 H14B 109.3 . . ?
H14A C14 H14B 108.0 . . ?
C2 C1 C5 119.1(3) . . ?
C2 C1 H1A 120.4 . . ?
C5 C1 H1A 120.4 . . ?
C7 C8 N1 104.0(2) . . ?
C7 C8 C14 134.5(3) . . ?
N1 C8 C14 121.5(2) . . ?
C17 C16 C15 118.4(2) . . ?
C17 C16 H16A 120.8 . . ?
C15 C16 H16A 120.8 . . ?
C4 C6 C5 120.7(3) . . ?
C4 C6 H6A 119.6 . . ?
C5 C6 H6A 119.6 . . ?
C11 C10 C9 120.8(3) . . ?
C11 C10 H10A 119.6 . . ?
C9 C10 H10A 119.6 . . ?
N1 C13 C12 118.7(3) . . ?
N1 C13 H13A 120.6 . . ?
C12 C13 H13A 120.6 . . ?
N3 C19 C18 124.5(2) . . ?
N3 C19 H19A 117.8 . . ?
C18 C19 H19A 117.8 . . ?
C19 C18 C17 117.9(2) . . ?
C19 C18 H18A 121.0 . . ?
C17 C18 H18A 121.0 . . ?
C16 C17 C18 119.8(2) . . ?
C16 C17 H17A 120.1 . . ?
C18 C17 H17A 120.1 . . ?
C3 C2 C1 121.7(3) . . ?
C3 C2 H2B 119.1 . . ?
C1 C2 H2B 119.1 . . ?
C10 C11 C12 119.6(3) . . ?
C10 C11 H11A 120.2 . . ?
C12 C11 H11A 120.2 . . ?
C13 C12 C11 119.0(3) . . ?
C13 C12 H12A 120.5 . . ?
C11 C12 H12A 120.5 . . ?
C3 C4 C6 120.9(3) . . ?
C3 C4 H4A 119.6 . . ?
C6 C4 H4A 119.6 . . ?
C4 C3 C2 120.3(3) . . ?
C4 C3 H3B 119.9 . . ?
C2 C3 H3B 119.9 . . ?
 
loop_
 _geom_hbond_atom_site_label_D 
 _geom_hbond_atom_site_label_H 
 _geom_hbond_atom_site_label_A 
 _geom_hbond_distance_DH 
 _geom_hbond_distance_HA 
 _geom_hbond_distance_DA 
 _geom_hbond_angle_DHA 
 _geom_hbond_site_symmetry_A 
C13 H13A N3  0.93 2.50 3.412(3) 166.4 2_656
N2 H2A N4  0.86 2.19 3.039(2) 169.1 7_566
 
_refine_diff_density_max    0.613
_refine_diff_density_min   -0.226
_refine_diff_density_rms    0.049



