# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_added_by_encifer
_database_code_depnum_ccdc_archive 'CCDC 1456637'
_audit_update_record             
;
2016-02-29 deposited with the CCDC.
2016-05-27 downloaded from the CCDC.
;
#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C14 H10 N2'
_chemical_formula_moiety         'C14 H10 N2'
_chemical_formula_weight         206.25
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,1/2-Y,1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   10.7559(2)
_cell_length_b                   5.60116(10)
_cell_length_c                   8.32910(10)
_cell_angle_alpha                90.0000
_cell_angle_beta                 99.8276(10)
_cell_angle_gamma                90.0000
_cell_volume                     494.428(15)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4506
_cell_measurement_theta_min      4.17
_cell_measurement_theta_max      68.16
_cell_measurement_temperature    296
#------------------------------------------------------------------------------
_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.055
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             216.00
_exptl_absorpt_coefficient_mu    0.652
_exptl_absorpt_correction_type   none

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

_diffrn_ambient_temperature      296
_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            5321
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_theta_max         68.16
_diffrn_reflns_theta_full        68.15
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# 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).
;
_reflns_number_total             895
_reflns_number_gt                852
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_gt           0.0347
_refine_ls_wR_factor_ref         0.0958
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_number_reflns         895
_refine_ls_number_parameters     93
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0557P)²+0.0875P] 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         0.170
_refine_diff_density_min         -0.200
_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
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(1992, 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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.40099(9) 0.24086(17) 0.51691(12) 0.0394(3) Uani 1.0 4 d . . .
C1 C 0.31446(11) 0.1226(2) 0.40084(13) 0.0364(3) Uani 1.0 4 d . . .
C2 C 0.19233(11) 0.1892(3) 0.33280(15) 0.0434(4) Uani 1.0 4 d . . .
C3 C 0.12448(12) 0.0411(3) 0.21747(16) 0.0483(4) Uani 1.0 4 d . . .
C4 C 0.17622(12) -0.1721(3) 0.17004(15) 0.0473(4) Uani 1.0 4 d . . .
C5 C 0.29680(12) -0.2414(2) 0.23758(14) 0.0404(4) Uani 1.0 4 d . . .
C6 C 0.36852(11) -0.09471(19) 0.35477(13) 0.0351(4) Uani 1.0 4 d . . .
C7 C 0.50814(10) 0.10067(19) 0.54782(13) 0.0350(3) Uani 1.0 4 d . . .
H1 H 0.1558(13) 0.340(3) 0.3658(16) 0.046(4) Uiso 1.0 4 d . . .
H2 H 0.0370(15) 0.088(3) 0.1663(18) 0.058(4) Uiso 1.0 4 d . . .
H3 H 0.1243(15) -0.275(3) 0.0934(19) 0.061(5) Uiso 1.0 4 d . . .
H4 H 0.3323(14) -0.391(3) 0.2041(16) 0.049(4) Uiso 1.0 4 d . . .
H5 H 0.3860(15) 0.380(3) 0.5743(18) 0.063(5) Uiso 1.0 4 d . . .



#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_molecular_graphics    'CrystalStructure 4.0'

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

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
N1 C1 1.3902(14) yes . .
N1 C7 1.3820(15) yes . .
C1 C2 1.3899(16) yes . .
C1 C6 1.4293(16) yes . .
C2 C3 1.3799(18) yes . .
C3 C4 1.402(2) yes . .
C4 C5 1.3784(18) yes . .
C5 C6 1.4021(16) yes . .
C6 C7 1.4324(15) yes . 3_656
C7 C7 1.3746(15) yes . 3_656
N1 H5 0.942(17) no . .
C2 H1 0.988(15) no . .
C3 H2 1.000(15) no . .
C4 H3 0.963(15) no . .
C5 H4 0.983(15) no . .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
C1 N1 C7 107.27(10) yes . . .
N1 C1 C2 129.02(11) yes . . .
N1 C1 C6 109.74(10) yes . . .
C2 C1 C6 121.24(10) yes . . .
C1 C2 C3 118.24(12) yes . . .
C2 C3 C4 121.32(12) yes . . .
C3 C4 C5 121.04(12) yes . . .
C4 C5 C6 119.12(12) yes . . .
C1 C6 C5 119.03(11) yes . . .
C1 C6 C7 104.34(9) yes . . 3_656
C5 C6 C7 136.63(11) yes . . 3_656
N1 C7 C6 141.36(10) yes . . 3_656
N1 C7 C7 109.79(9) yes . . 3_656
C6 C7 C7 108.86(10) yes 3_656 . 3_656
C1 N1 H5 126.5(9) no . . .
C7 N1 H5 125.8(9) no . . .
C1 C2 H1 120.5(8) no . . .
C3 C2 H1 121.2(8) no . . .
C2 C3 H2 119.0(9) no . . .
C4 C3 H2 119.6(9) no . . .
C3 C4 H3 118.8(10) no . . .
C5 C4 H3 120.1(10) no . . .
C4 C5 H4 120.6(8) no . . .
C6 C5 H4 120.3(8) no . . .

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_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C1 N1 C7 C6 -179.72(13) no . . . 3_656
C1 N1 C7 C7 0.98(13) no . . . 3_656
C7 N1 C1 C2 178.63(11) no . . . .
C7 N1 C1 C6 -1.13(12) no . . . .
N1 C1 C2 C3 179.49(11) no . . . .
N1 C1 C6 C5 -179.63(9) no . . . .
N1 C1 C6 C7 0.84(12) no . . . 3_656
C2 C1 C6 C5 0.58(17) no . . . .
C2 C1 C6 C7 -178.95(11) no . . . 3_656
C6 C1 C2 C3 -0.77(18) no . . . .
C1 C2 C3 C4 0.39(19) no . . . .
C2 C3 C4 C5 0.2(2) no . . . .
C3 C4 C5 C6 -0.38(19) no . . . .
C4 C5 C6 C1 0.00(17) no . . . .
C4 C5 C6 C7 179.34(12) no . . . 3_656
C1 C6 C7 N1 179.08(13) no . . 3_656 3_656
C1 C6 C7 C7 -0.23(12) no . . 3_656 .
C5 C6 C7 N1 -0.3(3) no . . 3_656 3_656
C5 C6 C7 C7 -179.63(13) no . . 3_656 .
N1 C7 C7 N1 180(100155) no . . 3_656 3_656
N1 C7 C7 C6 -0.46(13) no . . 3_656 .
C6 C7 C7 N1 0.46(13) no 3_656 . 3_656 3_656
C6 C7 C7 C6 -180(120048) no 3_656 . 3_656 .

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
N1 N1 3.4786(14) no . 3_656
N1 C5 3.5325(15) no . 3_656
C1 C4 2.7668(17) no . .
C2 C5 2.8307(18) no . .
C2 C7 3.5937(15) no . .
C2 C7 3.5931(16) no . 3_656
C3 C6 2.7842(17) no . .
C6 C6 3.5556(15) no . 3_656
N1 C1 3.5627(16) no . 4_555
N1 C6 3.5078(15) no . 4_555
C1 N1 3.5627(16) no . 4_554
C1 C5 3.5558(17) no . 4_545
C2 C5 3.5168(18) no . 1_565
C5 C1 3.5558(17) no . 4_544
C5 C2 3.5168(18) no . 1_545
C5 C6 3.5276(17) no . 4_544
C5 C7 3.5409(18) no . 2_645
C5 C7 3.5974(18) no . 4_544
C6 N1 3.5078(15) no . 4_554
C6 C5 3.5276(17) no . 4_545
C7 C5 3.5409(18) no . 2_655
C7 C5 3.5974(18) no . 4_545
N1 H1 2.777(13) no . .
N1 H4 3.473(13) no . 3_656
C1 H2 3.282(15) no . .
C1 H4 3.334(15) no . .
C2 H3 3.280(16) no . .
C2 H5 2.845(15) no . .
C3 H4 3.311(15) no . .
C4 H1 3.324(15) no . .
C5 H2 3.317(16) no . .
C5 H5 3.588(15) no . 3_656
C6 H1 3.351(14) no . .
C6 H3 3.271(15) no . .
C6 H5 3.213(17) no . .
C6 H5 3.056(16) no . 3_656
C7 H4 2.942(13) no . 3_656
C7 H5 3.158(17) no . 3_656
H1 H2 2.38(2) no . .
H1 H5 2.779(19) no . .
H2 H3 2.36(3) no . .
H3 H4 2.36(2) no . .
H4 H5 3.269(19) no . 3_656
N1 H4 3.304(14) no . 1_565
N1 H4 2.684(15) no . 4_545
N1 H5 3.307(17) no . 3_666
C1 H3 3.417(17) no . 4_545
C1 H4 3.200(15) no . 1_565
C1 H4 2.816(14) no . 4_545
C1 H5 2.951(16) no . 4_554
C2 H2 3.330(16) no . 2_555
C2 H3 3.569(17) no . 2_555
C2 H3 3.344(16) no . 4_545
C2 H4 3.080(15) no . 1_565
C2 H5 3.264(17) no . 4_554
C3 H1 3.183(14) no . 2_545
C3 H1 3.078(14) no . 4_554
C3 H2 3.311(16) no . 2_545
C3 H2 3.444(14) no . 3_555
C3 H3 3.486(17) no . 2_555
C3 H3 3.469(16) no . 4_545
C3 H5 3.267(17) no . 4_554
C4 H1 3.211(15) no . 1_545
C4 H1 3.534(14) no . 2_545
C4 H1 3.122(14) no . 4_554
C4 H2 3.160(17) no . 2_545
C4 H2 3.337(14) no . 3_555
C4 H5 3.004(17) no . 4_554
C5 H1 3.082(15) no . 1_545
C5 H5 3.517(15) no . 1_545
C5 H5 2.705(17) no . 4_554
C6 H4 3.526(15) no . 2_655
C6 H4 3.002(14) no . 4_545
C6 H5 3.453(17) no . 1_545
C6 H5 2.663(16) no . 4_554
C7 H4 2.929(15) no . 2_655
C7 H4 2.736(15) no . 4_545
C7 H5 3.393(15) no . 2_646
C7 H5 3.345(17) no . 3_666
H1 C3 3.183(14) no . 2_555
H1 C3 3.078(14) no . 4_555
H1 C4 3.211(15) no . 1_565
H1 C4 3.534(14) no . 2_555
H1 C4 3.122(14) no . 4_555
H1 C5 3.082(15) no . 1_565
H1 H2 2.47(2) no . 2_555
H1 H2 3.03(3) no . 4_555
H1 H3 3.11(2) no . 1_565
H1 H3 3.16(3) no . 2_555
H1 H3 3.14(3) no . 4_555
H1 H4 2.93(2) no . 1_565
H2 C2 3.330(16) no . 2_545
H2 C3 3.311(16) no . 2_555
H2 C3 3.444(14) no . 3_555
H2 C4 3.160(17) no . 2_555
H2 C4 3.337(14) no . 3_555
H2 H1 2.47(2) no . 2_545
H2 H1 3.03(3) no . 4_554
H2 H2 3.29(3) no . 2_545
H2 H2 3.29(3) no . 2_555
H2 H2 2.92(2) no . 3_555
H2 H3 2.97(3) no . 2_555
H2 H3 2.74(2) no . 3_555
H3 C1 3.417(17) no . 4_544
H3 C2 3.569(17) no . 2_545
H3 C2 3.344(16) no . 4_544
H3 C3 3.486(17) no . 2_545
H3 C3 3.469(16) no . 4_544
H3 H1 3.11(2) no . 1_545
H3 H1 3.16(3) no . 2_545
H3 H1 3.14(3) no . 4_554
H3 H2 2.97(3) no . 2_545
H3 H2 2.74(2) no . 3_555
H4 N1 3.304(14) no . 1_545
H4 N1 2.684(15) no . 4_544
H4 C1 3.200(15) no . 1_545
H4 C1 2.816(14) no . 4_544
H4 C2 3.080(15) no . 1_545
H4 C6 3.526(15) no . 2_645
H4 C6 3.002(14) no . 4_544
H4 C7 2.929(15) no . 2_645
H4 C7 2.736(15) no . 4_544
H4 H1 2.93(2) no . 1_545
H4 H5 3.30(2) no . 1_545
H4 H5 3.03(3) no . 4_544
H4 H5 3.15(3) no . 4_554
H5 N1 3.307(17) no . 3_666
H5 C1 2.951(16) no . 4_555
H5 C2 3.264(17) no . 4_555
H5 C3 3.267(17) no . 4_555
H5 C4 3.004(17) no . 4_555
H5 C5 3.517(15) no . 1_565
H5 C5 2.705(17) no . 4_555
H5 C6 3.453(17) no . 1_565
H5 C6 2.663(16) no . 4_555
H5 C7 3.393(15) no . 2_656
H5 C7 3.345(17) no . 3_666
H5 H4 3.30(2) no . 1_565
H5 H4 3.03(3) no . 4_545
H5 H4 3.15(3) no . 4_555
H5 H5 3.22(3) no . 3_666

#==============================================================================

#==============================================================================
# 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
#==============================================================================
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_added_by_encifer
_database_code_depnum_ccdc_archive 'CCDC 1456638'
_audit_update_record             
;
2016-02-29 deposited with the CCDC.
2016-05-27 downloaded from the CCDC.
;
#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C24 H18 N6'
_chemical_formula_moiety         'C24 H18 N6'
_chemical_formula_weight         390.45
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   6.899(6)
_cell_length_b                   8.655(6)
_cell_length_c                   9.670(5)
_cell_angle_alpha                70.09(5)
_cell_angle_beta                 69.22(5)
_cell_angle_gamma                69.33(7)
_cell_volume                     489.5(7)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      12.53
_cell_measurement_theta_max      17.21
_cell_measurement_temperature    298
#------------------------------------------------------------------------------
_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             204.00
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North, Phillips & Mathews, 1968)'
_exptl_absorpt_correction_T_min  0.899
_exptl_absorpt_correction_T_max  0.984

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

_diffrn_ambient_temperature      298
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71069
_diffrn_measurement_device_type  'Rigaku AFC7R'
_diffrn_measurement_method       ω-2θ
_diffrn_reflns_number            3407
_diffrn_reflns_av_R_equivalents  0.0515
_diffrn_reflns_theta_max         30.03
_diffrn_reflns_theta_full        30.02
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_standards_number         3
_diffrn_standards_interval_count 150
_diffrn_standards_decay_%        -0.830

#==============================================================================
# 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).
;
_reflns_number_total             2862
_reflns_number_gt                1072
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_gt           0.0750
_refine_ls_wR_factor_ref         0.2523
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2862
_refine_ls_number_parameters     136
_refine_ls_goodness_of_fit_ref   0.944
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.1209P)²+0.0000P] 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         0.270
_refine_diff_density_min         -0.250
_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 0.0033 0.0016
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(1992, 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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N13 N 0.0978(5) 0.2925(4) 0.4815(3) 0.0418(7) Uani 1.0 2 d . . .
N14 N 0.6099(5) 0.7708(4) 0.2770(3) 0.0413(7) Uani 1.0 2 d . . .
N15 N 0.4664(6) 1.0666(4) 0.3080(4) 0.0582(10) Uani 1.0 2 d . . .
C1 C 0.0707(5) 0.4653(4) 0.4395(4) 0.0377(8) Uani 1.0 2 d . . .
C2 C 0.1339(5) 0.5986(5) 0.3153(4) 0.0390(8) Uani 1.0 2 d . . .
C3 C 0.2641(6) 0.6121(6) 0.1655(4) 0.0503(10) Uani 1.0 2 d . . .
C4 C 0.2838(7) 0.7682(6) 0.0749(5) 0.0627(12) Uani 1.0 2 d . . .
C5 C 0.1767(7) 0.9148(6) 0.1288(5) 0.0667(13) Uani 1.0 2 d . . .
C6 C 0.0457(6) 0.9083(5) 0.2756(5) 0.0551(10) Uani 1.0 2 d . . .
C7 C 0.0235(5) 0.7487(5) 0.3693(4) 0.0428(9) Uani 1.0 2 d . . .
C8 C 0.7926(6) 0.4570(5) 0.2000(4) 0.0465(9) Uani 1.0 2 d . . .
C9 C 0.6460(5) 0.4744(4) 0.3539(4) 0.0363(8) Uani 1.0 2 d . . .
C10 C 0.5561(5) 0.6426(4) 0.3864(4) 0.0365(8) Uani 1.0 2 d . . .
C11 C 0.4103(5) 0.6590(4) 0.5350(4) 0.0366(8) Uani 1.0 2 d . . .
C12 C 0.5275(6) 0.9283(5) 0.2997(4) 0.0450(9) Uani 1.0 2 d . . .
H3 H 0.3366 0.5153 0.1281 0.0603 Uiso 1.0 2 calc R . .
H4 H 0.3703 0.7772 -0.0248 0.0753 Uiso 1.0 2 calc R . .
H5 H 0.1940 1.0196 0.0642 0.0801 Uiso 1.0 2 calc R . .
H6 H -0.0251 1.0067 0.3109 0.0661 Uiso 1.0 2 calc R . .
H8A H 0.7946 0.3539 0.1821 0.0557 Uiso 1.0 2 calc R . .
H8B H 0.9352 0.4532 0.1960 0.0557 Uiso 1.0 2 calc R . .
H8C H 0.7420 0.5528 0.1231 0.0557 Uiso 1.0 2 calc R . .
H11 H 0.3531 0.7666 0.5544 0.0439 Uiso 1.0 2 calc R . .
H13 H 0.1761 0.2225 0.4253 0.0502 Uiso 1.0 2 calc R . .



#==============================================================================
_computing_data_collection       WinAFC
_computing_cell_refinement       WinAFC
_computing_data_reduction        WinAFC
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_molecular_graphics    'CrystalStructure 4.0'

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

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
N13 C1 1.371(5) yes . .
N13 C7 1.383(4) yes . 2_566
N14 C10 1.304(4) yes . .
N14 C12 1.341(5) yes . .
N15 C12 1.141(6) yes . .
C1 C1 1.391(5) yes . 2_566
C1 C2 1.415(5) yes . .
C2 C3 1.398(5) yes . .
C2 C7 1.422(6) yes . .
C3 C4 1.360(6) yes . .
C4 C5 1.394(7) yes . .
C5 C6 1.381(6) yes . .
C6 C7 1.397(5) yes . .
C8 C9 1.496(5) yes . .
C9 C10 1.462(5) yes . .
C9 C11 1.346(5) yes . 2_666
C10 C11 1.453(4) yes . .
N13 H13 0.860 no . .
C3 H3 0.930 no . .
C4 H4 0.930 no . .
C5 H5 0.930 no . .
C6 H6 0.930 no . .
C8 H8A 0.960 no . .
C8 H8B 0.960 no . .
C8 H8C 0.960 no . .
C11 H11 0.930 no . .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
C1 N13 C7 107.6(3) yes . . 2_566
C10 N14 C12 119.4(3) yes . . .
N13 C1 C1 109.2(3) yes . . 2_566
N13 C1 C2 142.1(3) yes . . .
C1 C1 C2 108.7(3) yes 2_566 . .
C1 C2 C3 136.1(4) yes . . .
C1 C2 C7 104.6(3) yes . . .
C3 C2 C7 119.2(4) yes . . .
C2 C3 C4 119.4(4) yes . . .
C3 C4 C5 121.2(4) yes . . .
C4 C5 C6 121.7(4) yes . . .
C5 C6 C7 117.6(4) yes . . .
N13 C7 C2 109.9(3) yes 2_566 . .
N13 C7 C6 129.2(4) yes 2_566 . .
C2 C7 C6 121.0(3) yes . . .
C8 C9 C10 119.4(3) yes . . .
C8 C9 C11 122.7(4) yes . . 2_666
C10 C9 C11 117.9(3) yes . . 2_666
N14 C10 C9 117.1(3) yes . . .
N14 C10 C11 123.8(3) yes . . .
C9 C10 C11 119.1(3) yes . . .
C9 C11 C10 123.1(4) yes 2_666 . .
N14 C12 N15 174.8(4) yes . . .
C1 N13 H13 126.214 no . . .
C7 N13 H13 126.212 no 2_566 . .
C2 C3 H3 120.310 no . . .
C4 C3 H3 120.305 no . . .
C3 C4 H4 119.400 no . . .
C5 C4 H4 119.397 no . . .
C4 C5 H5 119.173 no . . .
C6 C5 H5 119.175 no . . .
C5 C6 H6 121.207 no . . .
C7 C6 H6 121.212 no . . .
C9 C8 H8A 109.470 no . . .
C9 C8 H8B 109.466 no . . .
C9 C8 H8C 109.470 no . . .
H8A C8 H8B 109.475 no . . .
H8A C8 H8C 109.476 no . . .
H8B C8 H8C 109.471 no . . .
C9 C11 H11 118.464 no 2_666 . .
C10 C11 H11 118.468 no . . .

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_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C1 N13 C7 C2 1.0(5) no . . 2_566 2_566
C1 N13 C7 C6 -178.9(4) no . . 2_566 2_566
C7 N13 C1 C1 -1.1(5) no 2_566 . . 2_566
C7 N13 C1 C2 -179.9(5) no 2_566 . . .
C12 N14 C10 C9 178.3(4) no . . . .
C12 N14 C10 C11 -0.3(6) no . . . .
N13 C1 C1 N13 180(262257) no . . 2_566 2_566
N13 C1 C1 C2 0.8(5) no . . 2_566 2_566
N13 C1 C2 C3 0.7(10) no . . . .
N13 C1 C2 C7 178.9(5) no . . . .
C1 C1 C2 C3 -178.0(4) no 2_566 . . .
C1 C1 C2 C7 0.2(5) no 2_566 . . .
C2 C1 C1 N13 -0.8(5) no . . 2_566 2_566
C2 C1 C1 C2 -180(262257) no . . 2_566 2_566
C1 C2 C3 C4 178.5(4) no . . . .
C1 C2 C7 N13 0.5(5) no . . . 2_566
C1 C2 C7 C6 -179.4(4) no . . . .
C3 C2 C7 N13 179.1(4) no . . . 2_566
C3 C2 C7 C6 -0.8(6) no . . . .
C7 C2 C3 C4 0.5(6) no . . . .
C2 C3 C4 C5 0.1(7) no . . . .
C3 C4 C5 C6 -0.3(8) no . . . .
C4 C5 C6 C7 -0.1(8) no . . . .
C5 C6 C7 N13 -179.3(4) no . . . 2_566
C5 C6 C7 C2 0.6(7) no . . . .
C8 C9 C10 N14 -0.0(6) no . . . .
C8 C9 C10 C11 178.7(3) no . . . .
C8 C9 C11 C10 -178.6(4) no . . 2_666 2_666
C10 C9 C11 C10 0.4(6) no . . 2_666 2_666
C11 C9 C10 N14 -179.1(4) no 2_666 . . .
C11 C9 C10 C11 -0.4(6) no 2_666 . . .
N14 C10 C11 C9 179.0(4) no . . . 2_666
C9 C10 C11 C9 0.4(6) no . . . 2_666

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
N13 N13 3.458(5) no . 2_566
N13 C3 3.507(5) no . .
N14 C8 2.795(6) no . .
N14 C11 3.569(5) no . 2_666
N15 C10 3.355(6) no . .
N15 C11 3.536(6) no . .
C1 C6 3.582(6) no . .
C1 C6 3.590(6) no . 2_566
C2 C2 3.531(5) no . 2_566
C2 C5 2.768(6) no . .
C3 C6 2.823(7) no . .
C4 C7 2.760(6) no . .
C9 C9 2.902(5) no . 2_666
C10 C10 2.823(5) no . 2_666
C11 C11 2.799(6) no . 2_666
C11 C12 2.771(5) no . .
N13 N14 3.393(6) no . 2_666
N13 N15 2.967(5) no . 1_545
N13 C9 3.414(6) no . 1_455
N13 C10 3.353(6) no . 2_666
N13 C11 3.435(6) no . 2_566
N13 C11 3.506(6) no . 2_666
N13 C12 3.528(6) no . 2_666
N14 N13 3.393(6) no . 2_666
N14 C2 3.493(6) no . 1_655
N14 C4 3.473(7) no . .
N14 C5 3.425(7) no . .
N14 C6 3.598(7) no . 1_655
N14 C7 3.207(6) no . 1_655
N15 N13 2.967(5) no . 1_565
N15 C4 3.511(6) no . 2_675
C1 C8 3.524(7) no . 1_455
C1 C9 3.285(7) no . 1_455
C1 C9 3.504(7) no . 2_666
C1 C10 3.483(6) no . 1_455
C1 C10 3.262(6) no . 2_666
C1 C11 3.430(6) no . 2_666
C2 N14 3.493(6) no . 1_455
C2 C9 3.429(6) no . .
C2 C10 3.389(7) no . .
C2 C11 3.571(7) no . .
C3 C8 3.508(7) no . .
C3 C9 3.375(7) no . .
C3 C10 3.536(7) no . .
C4 N14 3.473(7) no . .
C4 N15 3.511(6) no . 2_675
C5 N14 3.425(7) no . .
C5 C12 3.431(8) no . .
C6 N14 3.598(7) no . 1_455
C6 C12 3.445(7) no . 1_455
C6 C12 3.480(8) no . .
C7 N14 3.207(6) no . 1_455
C7 C10 3.589(7) no . 1_455
C7 C10 3.509(6) no . .
C7 C11 3.318(6) no . .
C7 C12 3.427(6) no . 1_455
C8 C1 3.524(7) no . 1_655
C8 C3 3.508(7) no . .
C9 N13 3.414(6) no . 1_655
C9 C1 3.285(7) no . 1_655
C9 C1 3.504(7) no . 2_666
C9 C2 3.429(6) no . .
C9 C3 3.375(7) no . .
C10 N13 3.353(6) no . 2_666
C10 C1 3.483(6) no . 1_655
C10 C1 3.262(6) no . 2_666
C10 C2 3.389(7) no . .
C10 C3 3.536(7) no . .
C10 C7 3.509(6) no . .
C10 C7 3.589(7) no . 1_655
C11 N13 3.435(6) no . 2_566
C11 N13 3.506(6) no . 2_666
C11 C1 3.430(6) no . 2_666
C11 C2 3.571(7) no . .
C11 C7 3.318(6) no . .
C12 N13 3.528(6) no . 2_666
C12 C5 3.431(8) no . .
C12 C6 3.480(8) no . .
C12 C6 3.445(7) no . 1_655
C12 C7 3.427(6) no . 1_655
N13 H3 3.4449 no . .
N13 H6 2.7658 no . 2_566
N14 H8B 3.0115 no . .
N14 H8C 2.5181 no . .
N14 H11 2.6348 no . .
N15 H11 2.9884 no . .
C1 H3 2.8937 no . .
C1 H13 3.0800 no . 2_566
C2 H4 3.2216 no . .
C2 H6 3.2976 no . .
C2 H13 3.0004 no . .
C2 H13 3.1247 no . 2_566
C3 H5 3.2269 no . .
C3 H13 3.5557 no . .
C4 H6 3.2651 no . .
C5 H3 3.2389 no . .
C6 H4 3.2522 no . .
C6 H13 2.8002 no . 2_566
C7 H3 3.2773 no . .
C7 H5 3.2184 no . .
C8 H11 2.6354 no . 2_666
C9 H11 3.3446 no . .
C10 H8A 3.3181 no . .
C10 H8B 2.9206 no . .
C10 H8C 2.6567 no . .
C10 H11 3.2510 no . 2_666
C11 H8A 2.5797 no . 2_666
C11 H8B 2.9840 no . 2_666
C11 H8C 3.1873 no . 2_666
C12 H11 2.4923 no . .
H3 H4 2.2857 no . .
H3 H13 3.2661 no . .
H4 H5 2.3039 no . .
H5 H6 2.3165 no . .
H6 H13 2.7667 no . 2_566
H8A H11 2.3912 no . 2_666
H8B H11 3.0885 no . 2_666
H8C H11 3.4282 no . 2_666
N13 H8B 3.0494 no . 1_455
N13 H11 3.4742 no . 2_566
N13 H11 3.5427 no . 2_666
N14 H5 3.2391 no . 2_675
N15 H3 3.5993 no . 1_565
N15 H4 2.6378 no . 2_675
N15 H6 3.5964 no . .
N15 H6 3.3689 no . 1_655
N15 H8A 3.5700 no . 1_565
N15 H11 3.0266 no . 2_676
N15 H13 2.1544 no . 1_565
C1 H8B 2.8692 no . 1_455
C2 H8B 2.8501 no . 1_455
C3 H3 3.3620 no . 2_665
C3 H8A 3.5796 no . .
C3 H8A 3.4281 no . 2_665
C3 H8B 2.9290 no . 1_455
C3 H8C 3.0478 no . .
C3 H8C 3.5584 no . 2_665
C4 H3 3.4391 no . 2_665
C4 H8A 3.2750 no . 2_665
C4 H8C 3.1586 no . .
C5 H5 3.4615 no . 2_575
C6 H8A 3.5649 no . 1_465
C6 H11 3.5589 no . 2_576
C7 H11 3.4233 no . .
C8 H3 3.2903 no . .
C8 H3 3.5001 no . 2_665
C8 H6 3.5459 no . 1_645
C8 H8B 3.5622 no . 2_765
C8 H8C 3.5983 no . 2_765
C9 H3 3.4202 no . .
C11 H6 3.5151 no . 2_576
C11 H13 3.5291 no . 2_666
C12 H4 3.0629 no . 2_675
C12 H5 3.5089 no . .
C12 H5 3.3178 no . 2_675
C12 H6 3.5966 no . .
C12 H6 3.4299 no . 1_655
C12 H13 3.0812 no . 1_565
C12 H13 3.5453 no . 2_666
H3 N15 3.5993 no . 1_545
H3 C3 3.3620 no . 2_665
H3 C4 3.4391 no . 2_665
H3 C8 3.2903 no . .
H3 C8 3.5001 no . 2_665
H3 C9 3.4202 no . .
H3 H3 2.7120 no . 2_665
H3 H4 2.8586 no . 2_665
H3 H8A 3.1252 no . .
H3 H8A 3.1600 no . 2_665
H3 H8B 2.8119 no . 1_455
H3 H8C 2.9093 no . .
H3 H8C 2.9453 no . 2_665
H4 N15 2.6378 no . 2_675
H4 C12 3.0629 no . 2_675
H4 H3 2.8586 no . 2_665
H4 H8A 2.8646 no . 2_665
H4 H8C 3.0964 no . .
H5 N14 3.2391 no . 2_675
H5 C5 3.4615 no . 2_575
H5 C12 3.5089 no . .
H5 C12 3.3178 no . 2_675
H5 H5 3.4791 no . 2_575
H5 H8A 3.4129 no . 1_465
H6 N15 3.3689 no . 1_455
H6 N15 3.5964 no . .
H6 C8 3.5459 no . 1_465
H6 C11 3.5151 no . 2_576
H6 C12 3.4299 no . 1_455
H6 C12 3.5966 no . .
H6 H8A 2.8355 no . 1_465
H6 H8B 3.5765 no . 1_465
H6 H11 2.6805 no . 2_576
H6 H13 3.3118 no . 1_565
H8A N15 3.5700 no . 1_545
H8A C3 3.5796 no . .
H8A C3 3.4281 no . 2_665
H8A C4 3.2750 no . 2_665
H8A C6 3.5649 no . 1_645
H8A H3 3.1252 no . .
H8A H3 3.1600 no . 2_665
H8A H4 2.8646 no . 2_665
H8A H5 3.4129 no . 1_645
H8A H6 2.8355 no . 1_645
H8A H8B 3.5817 no . 2_765
H8B N13 3.0494 no . 1_655
H8B C1 2.8692 no . 1_655
H8B C2 2.8501 no . 1_655
H8B C3 2.9290 no . 1_655
H8B C8 3.5622 no . 2_765
H8B H3 2.8119 no . 1_655
H8B H6 3.5765 no . 1_645
H8B H8A 3.5817 no . 2_765
H8B H8B 3.4398 no . 2_765
H8B H8C 3.1037 no . 2_765
H8B H13 2.9872 no . 1_655
H8C C3 3.0478 no . .
H8C C3 3.5584 no . 2_665
H8C C4 3.1586 no . .
H8C C8 3.5983 no . 2_765
H8C H3 2.9093 no . .
H8C H3 2.9453 no . 2_665
H8C H4 3.0964 no . .
H8C H8B 3.1037 no . 2_765
H8C H8C 3.5141 no . 2_765
H11 N13 3.4742 no . 2_566
H11 N13 3.5427 no . 2_666
H11 N15 3.0266 no . 2_676
H11 C6 3.5589 no . 2_576
H11 C7 3.4233 no . .
H11 H6 2.6805 no . 2_576
H11 H13 3.5980 no . 1_565
H11 H13 3.5547 no . 2_566
H11 H13 3.3585 no . 2_666
H13 N15 2.1544 no . 1_545
H13 C11 3.5291 no . 2_666
H13 C12 3.0812 no . 1_545
H13 C12 3.5453 no . 2_666
H13 H6 3.3118 no . 1_545
H13 H8B 2.9872 no . 1_455
H13 H11 3.5980 no . 1_545
H13 H11 3.5547 no . 2_566
H13 H11 3.3585 no . 2_666

#==============================================================================
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
N13 H13 N15 . . 1_545 2.967(5) 0.860 2.154 157.4 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
#==============================================================================
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_added_by_encifer
_database_code_depnum_ccdc_archive 'CCDC 1456639'
_audit_update_record             
;
2016-02-29 deposited with the CCDC.
2016-05-27 downloaded from the CCDC.
;
#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C28 H18 N6'
_chemical_formula_moiety         'C28 H18 N6'
_chemical_formula_weight         438.49
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   7.0445(3)
_cell_length_b                   8.9964(4)
_cell_length_c                   9.7681(4)
_cell_angle_alpha                74.396(2)
_cell_angle_beta                 71.111(3)
_cell_angle_gamma                65.2771(17)
_cell_volume                     525.57(4)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    3170
_cell_measurement_theta_min      4.84
_cell_measurement_theta_max      67.93
_cell_measurement_temperature    273
#------------------------------------------------------------------------------
_exptl_crystal_description       unknown
_exptl_crystal_colour            unknown
_exptl_crystal_size_max          0.254
_exptl_crystal_size_mid          0.026
_exptl_crystal_size_min          0.019
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             228.00
_exptl_absorpt_coefficient_mu    0.679
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.710
_exptl_absorpt_correction_T_max  0.987

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

_diffrn_ambient_temperature      273
_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            6096
_diffrn_reflns_av_R_equivalents  0.0723
_diffrn_reflns_theta_max         68.21
_diffrn_reflns_theta_full        68.22
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# 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).
;
_reflns_number_total             1894
_reflns_number_gt                591
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_gt           0.0965
_refine_ls_wR_factor_ref         0.2731
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         1894
_refine_ls_number_parameters     154
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.1000P)²+0.0000P] 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         0.260
_refine_diff_density_min         -0.310
_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
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(1992, 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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.1032(7) 0.4594(9) 0.3236(7) 0.0989(17) Uani 1.0 2 d . . .
N2 N 0.5006(9) 1.0269(8) 0.2863(7) 0.109(2) Uani 1.0 2 d . . .
N3 N 0.7575(8) 0.6933(7) -0.0193(6) 0.1022(19) Uani 1.0 2 d . . .
C1 C 0.1593(9) 0.7047(12) 0.1500(8) 0.101(3) Uani 1.0 2 d . . .
C2 C 0.1429(10) 0.8642(12) 0.1380(9) 0.110(3) Uani 1.0 2 d . . .
C3 C 0.0569(10) 0.9446(10) 0.2590(11) 0.107(3) Uani 1.0 2 d . . .
C4 C -0.0110(8) 0.8639(10) 0.3957(8) 0.094(2) Uani 1.0 2 d . . .
C5 C 0.0068(8) 0.7003(9) 0.4119(9) 0.0798(18) Uani 1.0 2 d . . .
C6 C 0.0949(8) 0.6217(10) 0.2859(9) 0.0812(19) Uani 1.0 2 d . . .
C7 C 0.0306(9) 0.4285(9) 0.4713(8) 0.084(3) Uani 1.0 2 d . . .
C8 C 0.5471(10) 0.8931(12) 0.2732(8) 0.093(3) Uani 1.0 2 d . . .
C9 C 0.6854(9) 0.7056(8) 0.1030(10) 0.086(2) Uani 1.0 2 d . . .
C10 C 0.5936(8) 0.7310(9) 0.2530(8) 0.0768(17) Uani 1.0 2 d . . .
C11 C 0.5539(7) 0.6077(8) 0.3707(7) 0.0681(16) Uani 1.0 2 d . . .
C12 C 0.4689(7) 0.6592(7) 0.5150(7) 0.0726(17) Uani 1.0 2 d . . .
C13 C 0.5824(7) 0.4446(8) 0.3608(7) 0.0681(16) Uani 1.0 2 d . . .
C14 C 0.6652(7) 0.3779(7) 0.2189(7) 0.0871(18) Uani 1.0 2 d . . .
H1 H 0.2132 0.6531 0.0675 0.1210 Uiso 1.0 2 calc R . .
H1A H 0.1467 0.3903 0.2639 0.1187 Uiso 1.0 2 calc R . .
H2 H 0.1904 0.9200 0.0467 0.1319 Uiso 1.0 2 calc R . .
H3 H 0.0449 1.0539 0.2478 0.1280 Uiso 1.0 2 calc R . .
H4 H -0.0685 0.9183 0.4767 0.1131 Uiso 1.0 2 calc R . .
H12 H 0.4492 0.7659 0.5225 0.0871 Uiso 1.0 2 calc R . .
H14A H 0.5578 0.3487 0.2038 0.1046 Uiso 1.0 2 calc R . .
H14B H 0.7938 0.2814 0.2224 0.1046 Uiso 1.0 2 calc R . .
H14C H 0.6968 0.4608 0.1397 0.1046 Uiso 1.0 2 calc R . .



#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_molecular_graphics    'CrystalStructure 4.0'

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

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
N1 C6 1.387(11) yes . .
N1 C7 1.359(9) yes . .
N2 C8 1.140(13) yes . .
N3 C9 1.153(10) yes . .
C1 C2 1.366(15) yes . .
C1 C6 1.373(10) yes . .
C2 C3 1.384(14) yes . .
C3 C4 1.376(11) yes . .
C4 C5 1.393(12) yes . .
C5 C6 1.416(12) yes . .
C5 C7 1.437(10) yes . 2_566
C7 C7 1.386(12) yes . 2_566
C8 C10 1.409(14) yes . .
C9 C10 1.435(11) yes . .
C10 C11 1.413(9) yes . .
C11 C12 1.460(10) yes . .
C11 C13 1.421(11) yes . .
C12 C13 1.366(8) yes . 2_666
C13 C14 1.502(9) yes . .
N1 H1A 0.860 no . .
C1 H1 0.930 no . .
C2 H2 0.930 no . .
C3 H3 0.930 no . .
C4 H4 0.930 no . .
C12 H12 0.930 no . .
C14 H14A 0.960 no . .
C14 H14B 0.960 no . .
C14 H14C 0.960 no . .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
C6 N1 C7 108.1(7) yes . . .
C2 C1 C6 118.9(8) yes . . .
C1 C2 C3 121.3(8) yes . . .
C2 C3 C4 120.5(9) yes . . .
C3 C4 C5 119.6(8) yes . . .
C4 C5 C6 118.6(7) yes . . .
C4 C5 C7 138.0(8) yes . . 2_566
C6 C5 C7 103.4(7) yes . . 2_566
N1 C6 C1 128.5(8) yes . . .
N1 C6 C5 110.4(6) yes . . .
C1 C6 C5 121.1(8) yes . . .
N1 C7 C5 141.8(8) yes . . 2_566
N1 C7 C7 108.9(7) yes . . 2_566
C5 C7 C7 109.2(7) yes 2_566 . 2_566
N2 C8 C10 176.4(9) yes . . .
N3 C9 C10 176.7(8) yes . . .
C8 C10 C9 113.3(6) yes . . .
C8 C10 C11 122.3(7) yes . . .
C9 C10 C11 124.4(7) yes . . .
C10 C11 C12 114.9(7) yes . . .
C10 C11 C13 126.6(7) yes . . .
C12 C11 C13 118.4(5) yes . . .
C11 C12 C13 121.9(7) yes . . 2_666
C11 C13 C12 119.6(6) yes . . 2_666
C11 C13 C14 123.6(5) yes . . .
C12 C13 C14 116.8(7) yes 2_666 . .
C6 N1 H1A 125.973 no . . .
C7 N1 H1A 125.972 no . . .
C2 C1 H1 120.536 no . . .
C6 C1 H1 120.535 no . . .
C1 C2 H2 119.355 no . . .
C3 C2 H2 119.357 no . . .
C2 C3 H3 119.748 no . . .
C4 C3 H3 119.748 no . . .
C3 C4 H4 120.207 no . . .
C5 C4 H4 120.213 no . . .
C11 C12 H12 119.032 no . . .
C13 C12 H12 119.032 no 2_666 . .
C13 C14 H14A 109.469 no . . .
C13 C14 H14B 109.474 no . . .
C13 C14 H14C 109.472 no . . .
H14A C14 H14B 109.468 no . . .
H14A C14 H14C 109.470 no . . .
H14B C14 H14C 109.473 no . . .

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_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C6 N1 C7 C5 -179.2(8) no . . . 2_566
C6 N1 C7 C7 1.8(7) no . . . 2_566
C7 N1 C6 C1 177.5(6) no . . . .
C7 N1 C6 C5 -2.3(7) no . . . .
C2 C1 C6 N1 -177.9(6) no . . . .
C2 C1 C6 C5 1.8(10) no . . . .
C6 C1 C2 C3 -2.0(10) no . . . .
C1 C2 C3 C4 1.2(11) no . . . .
C2 C3 C4 C5 -0.1(10) no . . . .
C3 C4 C5 C6 -0.1(9) no . . . .
C3 C4 C5 C7 175.8(7) no . . . 2_566
C4 C5 C6 N1 179.0(5) no . . . .
C4 C5 C6 C1 -0.8(9) no . . . .
C4 C5 C7 N1 2.0(15) no . . 2_566 2_566
C4 C5 C7 C7 -177.0(7) no . . 2_566 .
C6 C5 C7 N1 178.3(8) no . . 2_566 2_566
C6 C5 C7 C7 -0.7(7) no . . 2_566 .
C7 C5 C6 N1 1.8(7) no 2_566 . . .
C7 C5 C6 C1 -178.0(6) no 2_566 . . .
N1 C7 C7 N1 180(6) no 1_555 1_555 2_566 2_566
N1 C7 C7 C5 -0.7(7) no . . 2_566 .
C5 C7 C7 N1 0.7(7) no 2_566 . 2_566 2_566
C5 C7 C7 C5 -180(6) no 2_566 1_555 2_566 1_555
C8 C10 C11 C12 -2.2(8) no . . . .
C8 C10 C11 C13 175.8(6) no . . . .
C9 C10 C11 C12 177.2(6) no . . . .
C9 C10 C11 C13 -4.8(10) no . . . .
C10 C11 C12 C13 178.4(5) no . . . 2_666
C10 C11 C13 C12 -178.2(5) no . . . 2_666
C10 C11 C13 C14 1.1(8) no . . . .
C12 C11 C13 C12 -0.2(7) no . . . 2_666
C12 C11 C13 C14 179.0(4) no . . . .
C13 C11 C12 C13 0.2(8) no . . . 2_666
C11 C12 C13 C11 -0.3(8) no . . 2_666 2_666
C11 C12 C13 C14 179.1(4) no . . 2_666 2_666

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
N1 N1 3.427(9) no . 2_566
N1 C4 3.598(12) no . .
N1 C4 3.541(10) no . 2_566
N1 C6 3.597(9) no . 2_566
N2 C9 3.374(11) no . .
N2 C11 3.520(10) no . .
N2 C12 3.507(9) no . .
N3 C8 3.374(11) no . .
N3 C14 3.302(8) no . .
C1 C4 2.792(12) no . .
C1 C7 3.563(10) no . .
C1 C7 3.559(10) no . 2_566
C2 C5 2.766(11) no . .
C3 C6 2.750(13) no . .
C5 C5 3.578(11) no . 2_566
C8 C12 2.786(10) no . .
C9 C13 3.072(9) no . .
C9 C14 2.907(9) no . .
C10 C14 3.095(11) no . .
C11 C11 2.840(8) no . 2_666
C12 C12 2.793(10) no . 2_666
C13 C13 2.860(10) no . 2_666
N1 N3 3.297(10) no . 2_665
N1 C10 3.563(7) no . 1_455
N1 C11 3.439(6) no . 1_455
N1 C12 3.492(9) no . 2_666
N1 C13 3.455(9) no . .
N1 C14 3.551(7) no . .
N2 N3 3.487(8) no . 2_675
N2 C4 3.527(10) no . 1_655
N3 N1 3.297(10) no . 2_665
N3 N2 3.487(8) no . 2_675
C1 C9 3.510(12) no . 1_455
C1 C9 3.588(10) no . .
C1 C14 3.585(10) no . 2_665
C2 C9 3.408(9) no . .
C2 C10 3.344(11) no . .
C3 C8 3.331(12) no . .
C3 C10 3.440(8) no . .
C4 N2 3.527(10) no . 1_455
C4 C8 3.570(12) no . 1_455
C4 C12 3.517(8) no . .
C5 C8 3.495(10) no . 1_455
C5 C11 3.493(8) no . .
C5 C12 3.558(10) no . .
C6 C9 3.587(12) no . 1_455
C6 C10 3.347(9) no . 1_455
C6 C11 3.535(10) no . .
C6 C13 3.360(8) no . .
C7 C11 3.406(9) no . 1_455
C7 C11 3.593(11) no . 2_666
C7 C12 3.558(7) no . 1_455
C7 C12 3.316(9) no . 2_666
C7 C13 3.591(11) no . 1_455
C8 C3 3.331(12) no . .
C8 C4 3.570(12) no . 1_655
C8 C5 3.495(10) no . 1_655
C9 C1 3.588(10) no . .
C9 C1 3.510(12) no . 1_655
C9 C2 3.408(9) no . .
C9 C6 3.587(12) no . 1_655
C10 N1 3.563(7) no . 1_655
C10 C2 3.344(11) no . .
C10 C3 3.440(8) no . .
C10 C6 3.347(9) no . 1_655
C11 N1 3.439(6) no . 1_655
C11 C5 3.493(8) no . .
C11 C6 3.535(10) no . .
C11 C7 3.406(9) no . 1_655
C11 C7 3.593(11) no . 2_666
C12 N1 3.492(9) no . 2_666
C12 C4 3.517(8) no . .
C12 C5 3.558(10) no . .
C12 C7 3.558(7) no . 1_655
C12 C7 3.316(9) no . 2_666
C13 N1 3.455(9) no . .
C13 C6 3.360(8) no . .
C13 C7 3.591(11) no . 1_655
C14 N1 3.551(7) no . .
C14 C1 3.585(10) no . 2_665
N1 H1 2.7252 no . .
N1 H4 3.4973 no . 2_566
N2 H12 2.8680 no . .
N3 H14C 2.3538 no . .
C1 H1A 2.7743 no . .
C1 H3 3.2292 no . .
C2 H4 3.2357 no . .
C3 H1 3.2363 no . .
C4 H1A 3.5895 no . 2_566
C4 H2 3.2294 no . .
C5 H1 3.2707 no . .
C5 H1A 3.1278 no . .
C5 H1A 2.9993 no . 2_566
C5 H3 3.2331 no . .
C6 H2 3.1987 no . .
C6 H4 3.2608 no . .
C7 H1A 3.0626 no . 2_566
C7 H4 2.9332 no . 2_566
C8 H12 2.4058 no . .
C9 H14A 3.4972 no . .
C9 H14B 3.5004 no . .
C9 H14C 2.1054 no . .
C10 H12 2.5505 no . .
C10 H14C 2.6667 no . .
C11 H12 3.2470 no . 2_666
C11 H14A 3.1704 no . .
C11 H14B 3.1822 no . .
C11 H14C 2.6219 no . .
C12 H14A 2.6757 no . 2_666
C12 H14B 2.6700 no . 2_666
C12 H14C 3.2332 no . 2_666
C13 H12 3.3093 no . .
C14 H12 2.5496 no . 2_666
H1 H1A 2.7192 no . .
H1 H2 2.2947 no . .
H1A H4 3.3207 no . 2_566
H2 H3 2.3015 no . .
H3 H4 2.3056 no . .
H12 H14A 2.5864 no . 2_666
H12 H14B 2.5688 no . 2_666
H12 H14C 3.4703 no . 2_666
N1 H12 3.5209 no . 2_666
N1 H14A 2.8549 no . .
N2 H1A 3.1787 no . 1_565
N2 H2 3.3160 no . 2_675
N2 H3 3.2540 no . .
N2 H4 3.1091 no . 2_576
N2 H12 3.1533 no . 2_676
N2 H14A 2.9498 no . 1_565
N2 H14B 3.4998 no . 1_565
N3 H1 3.4322 no . 1_655
N3 H1 3.1889 no . 2_665
N3 H1A 2.4962 no . 2_665
N3 H2 3.5721 no . .
N3 H2 3.5795 no . 2_675
N3 H3 3.1621 no . 2_675
N3 H14A 3.4623 no . 2_665
N3 H14B 3.2059 no . 2_765
N3 H14C 3.4022 no . 2_765
C1 H14A 3.3085 no . .
C1 H14A 3.4317 no . 2_665
C1 H14B 3.5167 no . 2_665
C1 H14C 3.4765 no . .
C1 H14C 3.2246 no . 2_665
C2 H2 3.0949 no . 2_575
C3 H4 3.1835 no . 2_576
C3 H14B 2.8097 no . 1_465
C4 H4 2.8975 no . 2_576
C4 H12 3.5274 no . .
C4 H12 3.5351 no . 2_576
C4 H14B 3.5539 no . 1_465
C5 H12 3.5503 no . 1_455
C6 H14A 3.1589 no . .
C7 H12 3.3494 no . 2_666
C8 H2 3.4708 no . 2_675
C8 H3 3.2805 no . .
C8 H4 3.5108 no . 2_576
C9 H1 3.4570 no . 1_655
C9 H2 3.3512 no . .
C10 H2 3.5838 no . .
C14 H1 3.5973 no . .
C14 H1 2.7024 no . 2_665
C14 H1A 3.4912 no . .
C14 H3 3.0424 no . 1_645
H1 N3 3.4322 no . 1_455
H1 N3 3.1889 no . 2_665
H1 C9 3.4570 no . 1_455
H1 C14 3.5973 no . .
H1 C14 2.7024 no . 2_665
H1 H14A 3.1207 no . .
H1 H14A 2.6184 no . 2_665
H1 H14B 2.7450 no . 2_665
H1 H14C 3.3266 no . .
H1 H14C 2.2998 no . 2_665
H1A N2 3.1787 no . 1_545
H1A N3 2.4962 no . 2_665
H1A C14 3.4912 no . .
H1A H3 3.4421 no . 1_545
H1A H14A 2.6422 no . .
H1A H14B 3.1954 no . 1_455
H1A H14C 3.5092 no . 1_455
H2 N2 3.3160 no . 2_675
H2 N3 3.5721 no . .
H2 N3 3.5795 no . 2_675
H2 C2 3.0949 no . 2_575
H2 C8 3.4708 no . 2_675
H2 C9 3.3512 no . .
H2 C10 3.5838 no . .
H2 H2 2.7832 no . 2_575
H2 H14A 3.4291 no . 2_665
H2 H14B 3.5223 no . 2_665
H3 N2 3.2540 no . .
H3 N3 3.1621 no . 2_675
H3 C8 3.2805 no . .
H3 C14 3.0424 no . 1_465
H3 H1A 3.4421 no . 1_565
H3 H4 2.8323 no . 2_576
H3 H12 3.4584 no . 2_576
H3 H14A 3.4237 no . 1_465
H3 H14B 2.0889 no . 1_465
H3 H14C 3.5523 no . 1_465
H4 N2 3.1091 no . 2_576
H4 C3 3.1835 no . 2_576
H4 C4 2.8975 no . 2_576
H4 C8 3.5108 no . 2_576
H4 H3 2.8323 no . 2_576
H4 H4 2.2657 no . 2_576
H4 H12 3.4528 no . .
H4 H12 2.9816 no . 2_576
H4 H14B 3.5109 no . 1_465
H12 N1 3.5209 no . 2_666
H12 N2 3.1533 no . 2_676
H12 C4 3.5274 no . .
H12 C4 3.5351 no . 2_576
H12 C5 3.5503 no . 1_655
H12 C7 3.3494 no . 2_666
H12 H3 3.4584 no . 2_576
H12 H4 3.4528 no . .
H12 H4 2.9816 no . 2_576
H14A N1 2.8549 no . .
H14A N2 2.9498 no . 1_545
H14A N3 3.4623 no . 2_665
H14A C1 3.3085 no . .
H14A C1 3.4317 no . 2_665
H14A C6 3.1589 no . .
H14A H1 3.1207 no . .
H14A H1 2.6184 no . 2_665
H14A H1A 2.6422 no . .
H14A H2 3.4291 no . 2_665
H14A H3 3.4237 no . 1_645
H14B N2 3.4998 no . 1_545
H14B N3 3.2059 no . 2_765
H14B C1 3.5167 no . 2_665
H14B C3 2.8097 no . 1_645
H14B C4 3.5539 no . 1_645
H14B H1 2.7450 no . 2_665
H14B H1A 3.1954 no . 1_655
H14B H2 3.5223 no . 2_665
H14B H3 2.0889 no . 1_645
H14B H4 3.5109 no . 1_645
H14C N3 3.4022 no . 2_765
H14C C1 3.4765 no . .
H14C C1 3.2246 no . 2_665
H14C H1 3.3266 no . .
H14C H1 2.2998 no . 2_665
H14C H1A 3.5092 no . 1_655
H14C H3 3.5523 no . 1_645

#==============================================================================

#==============================================================================
# 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
#==============================================================================
