 
data_aj_329
 
_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
 'C18 H10 N4' 
_chemical_formula_weight          282.30

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            14
_space_group_name_H-M_alt         'P 21/c'
_space_group_name_Hall            '-P 2ybc'
 
_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+1/2, -z+1/2'
 '-x, -y, -z'
 'x, -y-1/2, z-1/2'
 
_cell_length_a                    8.824(9)
_cell_length_b                    5.800(6)
_cell_length_c                    13.935(12)
_cell_angle_alpha                 90
_cell_angle_beta                  94.06(3)
_cell_angle_gamma                 90
_cell_volume                      711.4(12)
_cell_formula_units_Z             2
_cell_measurement_temperature     293(2)
_cell_measurement_reflns_used     3002
_cell_measurement_theta_min       3.80
_cell_measurement_theta_max       25.77
 
_exptl_crystal_description        block
_exptl_crystal_colour             brown
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_density_diffrn     1.318          
_exptl_crystal_F_000              292
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.18
_exptl_crystal_size_mid           0.16
_exptl_crystal_size_min           0.13
_exptl_absorpt_coefficient_mu     0.082
_shelx_estimated_absorpt_T_min    ?
_shelx_estimated_absorpt_T_max    ?
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.6557
_exptl_absorpt_correction_T_max   0.7457
_exptl_absorpt_process_details    multi-scan
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       293(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_source                    ?
_diffrn_measurement_device_type   'Bruker APEX-II CCD'
_diffrn_measurement_method        'φ and ω scans'
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             11723
_diffrn_reflns_av_unetI/netI      0.0878
_diffrn_reflns_av_R_equivalents   0.0896
_diffrn_reflns_limit_h_min        -11
_diffrn_reflns_limit_h_max        11
_diffrn_reflns_limit_k_min        -7
_diffrn_reflns_limit_k_max        7
_diffrn_reflns_limit_l_min        -18
_diffrn_reflns_limit_l_max        18
_diffrn_reflns_theta_min          2.931
_diffrn_reflns_theta_max          28.079
_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              1724
_reflns_number_gt                 786
_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 APEX2'
_computing_cell_refinement        'Bruker SAINT'
_computing_data_reduction         'Bruker SAINT'
_computing_structure_solution     'SHELXS-97 (Sheldrick 2008)'
_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)+(0.0528P)²+0.1139P] 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      'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef        0.019(4)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_number_reflns          1724
_refine_ls_number_parameters      101
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.1794
_refine_ls_R_factor_gt            0.0625
_refine_ls_wR_factor_ref          0.1425
_refine_ls_wR_factor_gt           0.1084
_refine_ls_goodness_of_fit_ref    1.011
_refine_ls_restrained_S_all       1.011
_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
N1 N 0.43200(19) 0.2168(3) 0.50556(13) 0.0509(6) Uani 1 1 d . . . . .
N2 N -0.3744(2) 0.1921(4) 0.28227(14) 0.0583(6) Uani 1 1 d . . . . .
C1 C 0.5732(2) 0.1766(4) 0.53985(15) 0.0514(7) Uani 1 1 d . . . . .
H1 H 0.6289 0.2973 0.5687 0.062 Uiso 1 1 calc R U . . .
C2 C 0.3587(2) 0.0360(4) 0.46532(14) 0.0413(6) Uani 1 1 d . . . . .
C3 C -0.1539(2) 0.3336(4) 0.37274(16) 0.0536(7) Uani 1 1 d . . . . .
H3 H -0.1083 0.4532 0.4087 0.064 Uiso 1 1 calc R U . . .
C4 C 0.2051(2) 0.0720(4) 0.42726(14) 0.0479(6) Uani 1 1 d . . . . .
C5 C 0.0773(2) 0.0993(4) 0.39669(14) 0.0479(7) Uani 1 1 d . . . . .
C6 C -0.0759(2) 0.1323(4) 0.35806(14) 0.0398(6) Uani 1 1 d . . . . .
C7 C -0.3005(3) 0.3538(4) 0.33309(17) 0.0594(7) Uani 1 1 d . . . . .
H7 H -0.3513 0.4914 0.3428 0.071 Uiso 1 1 calc R U . . .
C8 C -0.1513(2) -0.0371(4) 0.30494(14) 0.0500(6) Uani 1 1 d . . . . .
H8 H -0.1033 -0.1759 0.2931 0.060 Uiso 1 1 calc R U . . .
C9 C -0.2982(2) 0.0007(4) 0.26958(16) 0.0571(7) Uani 1 1 d . . . . .
H9 H -0.3473 -0.1169 0.2342 0.068 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
N1 C1 1.323(3) . ?
N1 C2 1.334(3) . ?
N2 C9 1.316(3) . ?
N2 C7 1.319(3) . ?
C1 C2 1.376(3) 3_656 ?
C1 H1 0.9300 . ?
C2 C1 1.376(3) 3_656 ?
C2 C4 1.435(3) . ?
C3 C7 1.376(3) . ?
C3 C6 1.378(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.187(3) . ?
C5 C6 1.433(3) . ?
C6 C8 1.374(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.371(3) . ?
C8 H8 0.9300 . ?
C9 H9 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
C1 N1 C2 115.45(19) . . ?
C9 N2 C7 115.7(2) . . ?
N1 C1 C2 122.9(2) . 3_656 ?
N1 C1 H1 118.6 . . ?
C2 C1 H1 118.6 3_656 . ?
N1 C2 C1 121.69(19) . 3_656 ?
N1 C2 C4 117.3(2) . . ?
C1 C2 C4 121.0(2) 3_656 . ?
C7 C3 C6 118.5(2) . . ?
C7 C3 H3 120.7 . . ?
C6 C3 H3 120.7 . . ?
C5 C4 C2 179.0(2) . . ?
C4 C5 C6 179.0(2) . . ?
C8 C6 C3 117.3(2) . . ?
C8 C6 C5 121.0(2) . . ?
C3 C6 C5 121.7(2) . . ?
N2 C7 C3 124.8(2) . . ?
N2 C7 H7 117.6 . . ?
C3 C7 H7 117.6 . . ?
C9 C8 C6 119.2(2) . . ?
C9 C8 H8 120.4 . . ?
C6 C8 H8 120.4 . . ?
N2 C9 C8 124.4(2) . . ?
N2 C9 H9 117.8 . . ?
C8 C9 H9 117.8 . . ?
 
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
C2 N1 C1 C2 0.1(3) . . . 3_656 ?
C1 N1 C2 C1 -0.1(3) . . . 3_656 ?
C1 N1 C2 C4 179.95(18) . . . . ?
C7 C3 C6 C8 -0.6(3) . . . . ?
C7 C3 C6 C5 179.7(2) . . . . ?
C9 N2 C7 C3 -0.5(4) . . . . ?
C6 C3 C7 N2 0.9(4) . . . . ?
C3 C6 C8 C9 -0.1(3) . . . . ?
C5 C6 C8 C9 179.70(19) . . . . ?
C7 N2 C9 C8 -0.2(4) . . . . ?
C6 C8 C9 N2 0.5(3) . . . . ?
 
_refine_diff_density_max    0.169
_refine_diff_density_min   -0.159
_refine_diff_density_rms    0.044



