data_global
_audit_creation_date                               2019-08-09
_audit_creation_method                            'by CrystalStructure 4.3'
_audit_update_record                               ?

#==============================================================================
# PROCESSING SUMMARY (IUCr Office Use Only)

_journal_date_recd_electronic                      ?
_journal_date_from_coeditor                        ?
_journal_date_accepted                             ?
_journal_coeditor_code                             ?

#==============================================================================
# SUBMISSION DETAILS

_publ_contact_author_name                         'ENTER NAME'
_publ_contact_author_email                        'ENTER EMAIL ADDRESS'
_publ_contact_author_fax                          'ENTER FAX NUMBER'
_publ_contact_author_phone                        'ENTER PHONE NUMBER'
_publ_contact_letter
;
    ENTER TEXT OF LETTER
;
_publ_requested_journal                           'ENTER JOURNAL NAME HERE'
_publ_requested_category
                                               'CHOOSE FI FM FO CI CM CO or AD'
_publ_requested_coeditor_name                      ?

#==============================================================================
# TITLE AND AUTHOR LIST

_publ_section_title
;
    ENTER SECTION TITLE
;
_publ_section_title_footnote
;
    ENTER FOOTNOTE TO TITLE OF PAPER
;
loop_
_publ_author_name
_publ_author_footnote
_publ_author_address
' FIRST AUTHORS NAME '
;
  FIRST AUTHORS FOOTNOTES
;
;
  FIRST AUTHORS ADDRESS
;
_publ_section_synopsis
;
    ENTER SYNOPSIS
;

#==============================================================================
# TEXT

_publ_section_abstract
;
    ENTER ABSTRACT
;
_publ_section_comment
;
    ENTER TEXT
;
_publ_section_references
;
    ENTER OTHER REFERENCES

    Rigaku (2019). CrystalStructure. Version 4.3. 
    Rigaku Corporation, Tokyo, Japan.

    Sheldrick, G. M. (2014). Acta Cryst. (2014). A70, C1437.
    SHELXT Version 2018/2

    Sheldrick, G.M. (2008) SHELXL Version 2018/3, Acta Cryst. A64, 112-122.

    Rigaku (1995). ABSCOR. 
    Rigaku Corporation, Tokyo, Japan.

;
_publ_section_figure_captions
;
    ENTER FIGURE CAPTIONS
;
_publ_section_exptl_prep
;
    ENTER COMPOUND PREPARATION DETAILS
;
_publ_section_exptl_refinement
;
    ENTER SPECIAL DETAILS OF THE REFINEMENT
;

#==============================================================================
data_20190426

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum                             'C30 H28 N6'
_chemical_formula_moiety                          'C14 H8 N4, C16 H20 N2 '
_chemical_formula_weight                           472.59
_chemical_melting_point                            ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system                        orthorhombic
_space_group_name_H-M_alt                         'P n n m'
_space_group_name_Hall                            '-P 2 2n'
_space_group_IT_number                             58
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1   '+X,+Y,+Z'
2   '-X,-Y,+Z'
3   '1/2+X,1/2-Y,1/2-Z'
4   '1/2-X,1/2+Y,1/2-Z'
5   '-X,-Y,-Z'
6   '+X,+Y,-Z'
7   '-1/2-X,-1/2+Y,-1/2+Z'
8   '-1/2+X,-1/2-Y,-1/2+Z'
#------------------------------------------------------------------------------
_cell_length_a                                     22.0548(5)
_cell_length_b                                     8.5264(2)
_cell_length_c                                     6.69588(17)
_cell_angle_alpha                                  90.0000
_cell_angle_beta                                   90.0000
_cell_angle_gamma                                  90.0000
_cell_volume                                       1259.15(5)
_cell_formula_units_Z                              2
_cell_measurement_reflns_used                      3939
_cell_measurement_theta_min                        4.01
_cell_measurement_theta_max                        68.28
_cell_measurement_temperature                      274
#------------------------------------------------------------------------------
_exptl_crystal_description                         needle
_exptl_crystal_colour                              green
_exptl_crystal_size_max                            0.200
_exptl_crystal_size_mid                            0.050
_exptl_crystal_size_min                            0.040
_exptl_crystal_density_diffrn                      1.246
_exptl_crystal_density_meas                        ?
_exptl_crystal_density_method                     'not measured'
_exptl_crystal_F_000                               500.00
_exptl_absorpt_coefficient_mu                      0.596
_exptl_absorpt_correction_type                     multi-scan
_exptl_absorpt_process_details                    'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min                    0.777
_exptl_absorpt_correction_T_max                    0.976

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature                        274
_diffrn_radiation_type                            'Cu K\a'
_diffrn_radiation_wavelength                       1.54187
_diffrn_measurement_device_type                   'Rigaku R-AXIS RAPID'
_diffrn_measurement_method                         ω
_diffrn_detector_area_resol_mean                   10.000
_diffrn_reflns_number                              5938
_diffrn_reflns_av_unetI/netI                       0.0454
_diffrn_reflns_av_R_equivalents                    0.0445
_diffrn_reflns_theta_max                           67.686
_diffrn_reflns_theta_min                           4.009
_diffrn_reflns_theta_full                          67.686
_diffrn_measured_fraction_theta_max                0.967
_diffrn_measured_fraction_theta_full               0.967
_diffrn_reflns_Laue_measured_fraction_max          0.967
_diffrn_reflns_Laue_measured_fraction_full         0.967
_diffrn_reflns_point_group_measured_fraction_max   0.967
_diffrn_reflns_point_group_measured_fraction_full  0.967
_diffrn_reflns_limit_h_min                        -26
_diffrn_reflns_limit_h_max                         21
_diffrn_reflns_limit_k_min                        -8
_diffrn_reflns_limit_k_max                         10
_diffrn_reflns_limit_l_min                        -7
_diffrn_reflns_limit_l_max                         7
_diffrn_standards_number                           0
_diffrn_standards_interval_count                   .
_diffrn_standards_decay_%                          ?
_reflns_number_total                               1202
_reflns_number_gt                                  560
_reflns_threshold_expression                       F²>2.0σ(F²)
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .

#==============================================================================
# REFINEMENT DATA

_refine_special_details
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef                   Fsqd
_refine_ls_R_factor_all                            0.1143
_refine_ls_R_factor_gt                             0.0611
_refine_ls_wR_factor_ref                           0.2204
_refine_ls_wR_factor_gt                            0.1635
_refine_ls_number_restraints                       0
_refine_ls_hydrogen_treatment                      constr
_refine_ls_number_reflns                           1202
_refine_ls_number_parameters                       116
_refine_ls_goodness_of_fit_ref                     0.998
_refine_ls_weighting_scheme                        calc
_refine_ls_weighting_details
                   'w = 1/[σ²(Fo²)+(0.1232P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens                     geom
_atom_sites_solution_primary                       direct
_atom_sites_solution_secondary                     difmap
_refine_ls_shift/su_max                            0.000
_refine_diff_density_max                           0.40
_refine_diff_density_min                          -0.17
_refine_ls_extinction_method                       none
_refine_ls_extinction_coef                         ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
  'C' 'C'  0.0181 0.0091 
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
  'H' 'H'  0.0000 0.0000 
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
  'N' 'N'  0.0311 0.0180 
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.21557(13) 0.8403(4) 0.500000 0.0725(12) Uani 1 2 d S T P . .
H1A H 0.225518 0.742825 0.500000 0.087 Uiso 1 2 calc R U P . .
H1B H 0.243241 0.911403 0.500000 0.087 Uiso 1 2 calc R U P . .
N2 N 0.3516(2) 0.0875(5) 0.500000 0.0947(16) Uani 1 2 d S T P . .
N3 N 0.28153(18) 0.5327(5) 0.500000 0.0877(14) Uani 1 2 d S T P . .
C1 C 0.15562(17) 0.8825(5) 0.500000 0.0549(12) Uani 1 2 d S T P . .
C2 C 0.10911(18) 0.7692(5) 0.500000 0.0533(12) Uani 1 2 d S T P . .
C3 C 0.13984(18) 1.0448(5) 0.500000 0.0571(12) Uani 1 2 d S T P . .
C4 C 0.05010(17) 0.8176(5) 0.500000 0.0529(11) Uani 1 2 d S T P . .
H4 H 0.020017 0.741227 0.500000 0.063 Uiso 1 2 calc R U P . .
C5 C 0.07979(17) 1.0853(5) 0.500000 0.0569(12) Uani 1 2 d S T P . .
H5 H 0.069995 1.191346 0.500000 0.068 Uiso 1 2 calc R U P . .
C6 C 0.03191(16) 0.9758(5) 0.500000 0.0519(11) Uani 1 2 d S T P . .
C7 C 0.1252(2) 0.5956(5) 0.500000 0.0701(14) Uani 1 2 d S T P . .
H7A H 0.088690 0.534346 0.500000 0.105 Uiso 1 2 calc R U P . .
H7B H 0.148548 0.571500 0.617063 0.105 Uiso 0.5 1 calc R U P . .
H7C H 0.148548 0.571500 0.382937 0.105 Uiso 0.5 1 calc R U P . .
C8 C 0.18922(19) 1.1687(6) 0.500000 0.0730(14) Uani 1 2 d S T P . .
H8A H 0.171062 1.270999 0.500000 0.109 Uiso 1 2 calc R U P . .
H8B H 0.213924 1.156711 0.382937 0.109 Uiso 0.5 1 calc R U P . .
H8C H 0.213924 1.156711 0.617063 0.109 Uiso 0.5 1 calc R U P . .
C9 C 0.36751(19) 0.2148(6) 0.500000 0.0633(13) Uani 1 2 d S T P . .
C10 C 0.3276(2) 0.4697(6) 0.500000 0.0642(13) Uani 1 2 d S T P . .
C11 C 0.38147(17) 0.3786(5) 0.500000 0.0585(13) Uani 1 2 d S T P . .
C12 C 0.43996(16) 0.4398(5) 0.500000 0.0503(11) Uani 1 2 d S T P A .
C13 C 0.49180(17) 0.3367(5) 0.500000 0.0599(13) Uani 1 2 d S T P . .
H13 H 0.485923 0.228732 0.500000 0.072 Uiso 0.589(7) 2 calc R U P A 1
C15A C 0.5967(3) 0.2617(9) 0.500000 0.075(3) Uani 0.589(7) 2 d S T P A 1
H15A H 0.576571 0.161891 0.500000 0.113 Uiso 0.589(7) 2 calc R U P A 1
H15B H 0.621597 0.270468 0.617063 0.113 Uiso 0.294(4) 1 calc R U P A 1
H15C H 0.621597 0.270468 0.382937 0.113 Uiso 0.294(4) 1 calc R U P A 1
C15B C 0.4921(4) 0.1541(10) 0.500000 0.059(3) Uani 0.411(7) 2 d S T P A 2
H15D H 0.451130 0.116087 0.500000 0.089 Uiso 0.411(7) 2 calc R U P A 2
H15E H 0.512687 0.116779 0.382937 0.089 Uiso 0.206(4) 1 calc R U P A 2
H15F H 0.512688 0.116779 0.617063 0.089 Uiso 0.206(4) 1 calc R U P A 2
C14 C 0.54872(18) 0.3948(5) 0.500000 0.0560(12) Uani 1 2 d S T P A .
H14 H 0.581369 0.325824 0.500000 0.067 Uiso 0.411(7) 2 calc R U P A 2


#==============================================================================
_computing_data_collection                        'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement                        'RAPID AUTO'
_computing_data_reduction                         'RAPID AUTO'
_computing_structure_solution
                                      'SHELXT Version 2018/2 (Sheldrick, 2014)'
_computing_structure_refinement
                                      'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_publication_material
                                          'CrystalStructure 4.3 (Rigaku, 2019)'
_computing_molecular_graphics                     'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_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 1.370(4) . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
N2 C9 1.140(6) . ?
N3 C10 1.150(5) . ?
C1 C2 1.409(5) . ?
C1 C3 1.427(5) . ?
C2 C4 1.365(5) . ?
C2 C7 1.522(5) . ?
C3 C5 1.369(5) . ?
C3 C8 1.517(6) . ?
C4 C6 1.407(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.410(5) . ?
C5 H5 0.9300 . ?
C6 C6 1.467(7) 5_576 ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C11 1.430(6) . ?
C10 C11 1.419(6) . ?
C11 C12 1.392(5) . ?
C12 C14 1.431(5) 5_666 ?
C12 C13 1.442(5) . ?
C13 C14 1.350(5) . ?
C13 C15B 1.557(9) . ?
C13 H13 0.9300 . ?
C15A C14 1.552(8) . ?
C15A H15A 0.9600 . ?
C15A H15B 0.9600 . ?
C15A H15C 0.9600 . ?
C15B H15D 0.9600 . ?
C15B H15E 0.9600 . ?
C15B H15F 0.9600 . ?
C14 H14 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 H1A 120.0 . . ?
C1 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
N1 C1 C2 121.5(4) . . ?
N1 C1 C3 119.3(4) . . ?
C2 C1 C3 119.2(4) . . ?
C4 C2 C1 119.1(4) . . ?
C4 C2 C7 121.1(4) . . ?
C1 C2 C7 119.8(4) . . ?
C5 C3 C1 118.7(4) . . ?
C5 C3 C8 121.3(4) . . ?
C1 C3 C8 120.0(4) . . ?
C2 C4 C6 124.2(4) . . ?
C2 C4 H4 117.9 . . ?
C6 C4 H4 117.9 . . ?
C3 C5 C6 123.9(4) . . ?
C3 C5 H5 118.0 . . ?
C6 C5 H5 118.0 . . ?
C4 C6 C5 114.9(3) . . ?
C4 C6 C6 122.9(5) . 5_576 ?
C5 C6 C6 122.2(5) . 5_576 ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C3 C8 H8A 109.5 . . ?
C3 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C3 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N2 C9 C11 174.5(5) . . ?
N3 C10 C11 174.6(5) . . ?
C12 C11 C10 124.8(4) . . ?
C12 C11 C9 124.5(4) . . ?
C10 C11 C9 110.8(4) . . ?
C11 C12 C14 122.1(4) . 5_666 ?
C11 C12 C13 120.4(4) . . ?
C14 C12 C13 117.5(3) 5_666 . ?
C14 C13 C12 120.9(4) . . ?
C14 C13 C15B 111.3(5) . . ?
C12 C13 C15B 127.8(5) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C14 C15A H15A 109.5 . . ?
C14 C15A H15B 109.5 . . ?
H15A C15A H15B 109.5 . . ?
C14 C15A H15C 109.5 . . ?
H15A C15A H15C 109.5 . . ?
H15B C15A H15C 109.5 . . ?
C13 C15B H15D 109.5 . . ?
C13 C15B H15E 109.5 . . ?
H15D C15B H15E 109.5 . . ?
C13 C15B H15F 109.5 . . ?
H15D C15B H15F 109.5 . . ?
H15E C15B H15F 109.5 . . ?
C13 C14 C12 121.6(4) . 5_666 ?
C13 C14 C15A 111.5(5) . . ?
C12 C14 C15A 127.0(4) 5_666 . ?
C13 C14 H14 119.2 . . ?
C12 C14 H14 119.2 5_666 . ?

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
N1 C1 C2 C4 180.0 . . . . ?
C3 C1 C2 C4 0.0 . . . . ?
N1 C1 C2 C7 0.0 . . . . ?
C3 C1 C2 C7 180.0 . . . . ?
N1 C1 C3 C5 180.0 . . . . ?
C2 C1 C3 C5 0.0 . . . . ?
N1 C1 C3 C8 0.0 . . . . ?
C2 C1 C3 C8 180.0 . . . . ?
C1 C2 C4 C6 0.0 . . . . ?
C7 C2 C4 C6 180.0 . . . . ?
C1 C3 C5 C6 0.0 . . . . ?
C8 C3 C5 C6 180.0 . . . . ?
C2 C4 C6 C5 0.0 . . . . ?
C2 C4 C6 C6 180.0 . . . 5_576 ?
C3 C5 C6 C4 0.0 . . . . ?
C3 C5 C6 C6 180.0 . . . 5_576 ?
C10 C11 C12 C14 0.0 . . . 5_666 ?
C9 C11 C12 C14 180.0 . . . 5_666 ?
C10 C11 C12 C13 180.0 . . . . ?
C9 C11 C12 C13 0.0 . . . . ?
C11 C12 C13 C14 180.0 . . . . ?
C14 C12 C13 C14 0.0 5_666 . . . ?
C11 C12 C13 C15B 0.0 . . . . ?
C14 C12 C13 C15B 180.0 5_666 . . . ?
C12 C13 C14 C12 0.0 . . . 5_666 ?
C15B C13 C14 C12 180.0 . . . 5_666 ?
C12 C13 C14 C15A 180.0 . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1A N3 . . . 2.999(5) 0.860 2.176 160.2 no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.





#==============================================================================
#     End of CIF
#==============================================================================
