####################################################################### 
# 
# 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_TAPP
_audit_block_doi                 10.5517/cct2pvd
_database_code_depnum_ccdc_archive 'CCDC 747374'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1002/chem.200902596 2010
_audit_update_record             
;
2009-09-09 deposited with the CCDC.
2017-11-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H10 N4'
_chemical_melting_point          ?

_exptl_crystal_description       needle
_exptl_crystal_colour            orange

_diffrn_ambient_temperature      100(2)
_chemical_formula_weight         330.34

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   'P 21/c'
_symmetry_int_tables_number      14

_chemical_absolute_configuration .

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   3.7080(2)
_cell_length_b                   11.2525(6)
_cell_length_c                   16.6569(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.4040(13)
_cell_angle_gamma                90.00
_cell_volume                     689.20(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6995
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      32.02
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.592
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             340
_exptl_absorpt_coefficient_mu    0.098

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8021
_exptl_absorpt_correction_T_max  0.8623
_exptl_absorpt_process_details   
;
multi-scan from symmetry-related measurements (Blessing 1995)
SADABS (Sheldrick & Bruker AXS, 2004-2008)
;

_exptl_special_details           
;
?
;

_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD-PXL-KAF2 (Bruker AXS Smart 1000)'
_diffrn_measurement_method       'φ- and ω-scans'
_diffrn_detector_area_resol_mean 8.19
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            34441
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_av_sigmaI/netI    0.0201
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.19
_diffrn_reflns_theta_max         32.02
_reflns_number_total             2331
_reflns_number_gt                1915
_reflns_threshold_expression     >2sigma(I)


_computing_data_collection       'SMART (Bruker AXS, 1997-2003)'
_computing_cell_refinement       
;
SAINT (Bruker AXS, 1997-2008).
;

_computing_data_reduction        'SAINT (Bruker AXS, 1997-2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 1980-2008)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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)+(0.1162P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap

_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2331
_refine_ls_number_parameters     138
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0580
_refine_ls_R_factor_gt           0.0503
_refine_ls_wR_factor_ref         0.1553
_refine_ls_wR_factor_gt          0.1485
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_restrained_S_all      1.094
_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
N2 N -0.15177(19) 0.07357(6) 0.08455(4) 0.0116(2) Uani 1 1 d . . .
N1 N 0.1855(2) 0.16390(6) 0.20200(4) 0.01171(19) Uani 1 1 d . . .
C9 C -0.1694(2) 0.39780(7) -0.04040(5) 0.0082(2) Uani 1 1 d . . .
C7 C 0.1757(2) 0.49151(7) 0.08136(5) 0.00830(19) Uani 1 1 d . . .
C8 C 0.0066(2) 0.39125(7) 0.04049(5) 0.00789(19) Uani 1 1 d . . .
C3 C 0.0121(2) 0.28035(7) 0.08183(5) 0.00834(19) Uani 1 1 d . . .
C2 C 0.1820(2) 0.26852(7) 0.16241(5) 0.00945(19) Uani 1 1 d . . .
C6 C 0.3481(2) 0.47693(7) 0.16324(5) 0.0100(2) Uani 1 1 d . . .
C4 C -0.1550(2) 0.17814(7) 0.04461(5) 0.00925(19) Uani 1 1 d . . .
C10 C -0.3380(2) 0.29216(7) -0.07687(5) 0.0100(2) Uani 1 1 d . . .
C11 C -0.3336(2) 0.18668(7) -0.03688(5) 0.0109(2) Uani 1 1 d . . .
C5 C 0.3530(2) 0.37058(7) 0.20198(5) 0.0108(2) Uani 1 1 d . . .
C1 C 0.0183(2) 0.07376(7) 0.16006(5) 0.0124(2) Uani 1 1 d . . .
H11 H -0.456(3) 0.1134(11) -0.0590(7) 0.018(3) Uiso 1 1 d . . .
H5 H 0.472(3) 0.3591(12) 0.2591(8) 0.024(3) Uiso 1 1 d . . .
H10 H -0.463(3) 0.2997(11) -0.1336(7) 0.019(3) Uiso 1 1 d . . .
H1 H 0.026(4) -0.0032(12) 0.1891(8) 0.027(3) Uiso 1 1 d . . .
H6 H 0.458(4) 0.5456(11) 0.1925(8) 0.028(3) Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N2 0.0127(3) 0.0091(4) 0.0132(4) 0.0018(2) 0.0015(3) -0.0007(2)
N1 0.0134(3) 0.0103(4) 0.0112(3) 0.0019(2) 0.0007(3) 0.0005(2)
C9 0.0081(4) 0.0080(4) 0.0082(4) -0.0012(3) 0.0004(3) -0.0004(3)
C7 0.0084(4) 0.0086(4) 0.0077(4) -0.0010(3) 0.0003(3) 0.0001(3)
C8 0.0080(4) 0.0078(4) 0.0078(4) -0.0007(3) 0.0010(3) -0.0001(3)
C3 0.0081(4) 0.0080(4) 0.0089(4) -0.0001(3) 0.0010(3) -0.0001(3)
C2 0.0092(4) 0.0097(4) 0.0094(4) 0.0010(3) 0.0012(3) 0.0011(3)
C6 0.0111(4) 0.0100(4) 0.0085(4) -0.0013(3) -0.0001(3) -0.0004(3)
C4 0.0094(3) 0.0077(4) 0.0108(4) -0.0002(3) 0.0019(3) -0.0002(3)
C10 0.0109(4) 0.0093(4) 0.0093(4) -0.0020(3) -0.0011(3) -0.0009(3)
C11 0.0113(4) 0.0095(4) 0.0113(4) -0.0018(3) -0.0002(3) -0.0015(3)
C5 0.0119(4) 0.0118(4) 0.0079(4) -0.0010(3) -0.0012(3) 0.0002(3)
C1 0.0138(4) 0.0103(4) 0.0129(4) 0.0026(3) 0.0014(3) -0.0007(3)

_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
N2 C1 1.3323(11) . ?
N2 C4 1.3510(10) . ?
N1 C1 1.3378(10) . ?
N1 C2 1.3486(10) . ?
C9 C7 1.4189(11) 3_565 ?
C9 C8 1.4214(11) . ?
C9 C10 1.4406(11) . ?
C7 C9 1.4189(11) 3_565 ?
C7 C8 1.4210(11) . ?
C7 C6 1.4391(11) . ?
C8 C3 1.4241(11) . ?
C3 C4 1.4114(11) . ?
C3 C2 1.4136(11) . ?
C2 C5 1.4309(11) . ?
C6 C5 1.3586(11) . ?
C6 H6 0.975(14) . ?
C4 C11 1.4347(11) . ?
C10 C11 1.3602(11) . ?
C10 H10 1.000(12) . ?
C11 H11 0.988(12) . ?
C5 H5 1.005(13) . ?
C1 H1 0.991(14) . ?

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 N2 C4 115.89(7) . . ?
C1 N1 C2 115.59(7) . . ?
C7 C9 C8 118.58(7) 3_565 . ?
C7 C9 C10 122.84(7) 3_565 . ?
C8 C9 C10 118.57(7) . . ?
C9 C7 C8 119.19(7) 3_565 . ?
C9 C7 C6 122.24(7) 3_565 . ?
C8 C7 C6 118.56(7) . . ?
C7 C8 C9 122.23(8) . . ?
C7 C8 C3 119.09(8) . . ?
C9 C8 C3 118.69(7) . . ?
C4 C3 C2 117.20(7) . . ?
C4 C3 C8 121.57(8) . . ?
C2 C3 C8 121.23(7) . . ?
N1 C2 C3 121.43(7) . . ?
N1 C2 C5 119.97(7) . . ?
C3 C2 C5 118.59(7) . . ?
C5 C6 C7 121.85(7) . . ?
C5 C6 H6 118.8(8) . . ?
C7 C6 H6 119.3(8) . . ?
N2 C4 C3 121.19(8) . . ?
N2 C4 C11 119.86(7) . . ?
C3 C4 C11 118.95(7) . . ?
C11 C10 C9 122.44(7) . . ?
C11 C10 H10 120.8(7) . . ?
C9 C10 H10 116.8(7) . . ?
C10 C11 C4 119.78(7) . . ?
C10 C11 H11 124.7(7) . . ?
C4 C11 H11 115.5(7) . . ?
C6 C5 C2 120.67(7) . . ?
C6 C5 H5 122.7(7) . . ?
C2 C5 H5 116.6(8) . . ?
N2 C1 N1 128.70(8) . . ?
N2 C1 H1 116.1(8) . . ?
N1 C1 H1 115.2(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
C9 C7 C8 C9 0.06(14) 3_565 . . . ?
C6 C7 C8 C9 -179.93(7) . . . . ?
C9 C7 C8 C3 -179.76(7) 3_565 . . . ?
C6 C7 C8 C3 0.25(13) . . . . ?
C7 C9 C8 C7 -0.06(14) 3_565 . . . ?
C10 C9 C8 C7 -179.20(7) . . . . ?
C7 C9 C8 C3 179.76(7) 3_565 . . . ?
C10 C9 C8 C3 0.62(12) . . . . ?
C7 C8 C3 C4 179.26(7) . . . . ?
C9 C8 C3 C4 -0.56(13) . . . . ?
C7 C8 C3 C2 0.00(13) . . . . ?
C9 C8 C3 C2 -179.82(7) . . . . ?
C1 N1 C2 C3 -0.12(12) . . . . ?
C1 N1 C2 C5 179.90(7) . . . . ?
C4 C3 C2 N1 0.21(12) . . . . ?
C8 C3 C2 N1 179.50(7) . . . . ?
C4 C3 C2 C5 -179.81(7) . . . . ?
C8 C3 C2 C5 -0.52(13) . . . . ?
C9 C7 C6 C5 -179.97(7) 3_565 . . . ?
C8 C7 C6 C5 0.02(13) . . . . ?
C1 N2 C4 C3 -0.21(12) . . . . ?
C1 N2 C4 C11 -179.64(7) . . . . ?
C2 C3 C4 N2 -0.03(12) . . . . ?
C8 C3 C4 N2 -179.32(7) . . . . ?
C2 C3 C4 C11 179.40(7) . . . . ?
C8 C3 C4 C11 0.11(13) . . . . ?
C7 C9 C10 C11 -179.35(7) 3_565 . . . ?
C8 C9 C10 C11 -0.26(13) . . . . ?
C9 C10 C11 C4 -0.20(13) . . . . ?
N2 C4 C11 C10 179.71(7) . . . . ?
C3 C4 C11 C10 0.27(13) . . . . ?
C7 C6 C5 C2 -0.55(13) . . . . ?
N1 C2 C5 C6 -179.22(7) . . . . ?
C3 C2 C5 C6 0.80(13) . . . . ?
C4 N2 C1 N1 0.33(14) . . . . ?
C2 N1 C1 N2 -0.16(14) . . . . ?

_diffrn_measured_fraction_theta_max 0.968
_diffrn_reflns_theta_full        31.00
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.700
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.084
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'



_audit_block_code                ga_sm1
_audit_block_refno               539





