# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2014

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#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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#  data retrieval see:
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data_1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H12 N2'
_chemical_formula_weight         208.26

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   P21/c

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                   9.026(6)
_cell_length_b                   23.908(16)
_cell_length_c                   10.185(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.752(12)
_cell_angle_gamma                90.00
_cell_volume                     2198(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1786
_cell_measurement_theta_min      2.63
_cell_measurement_theta_max      24.41

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.17
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             880
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9850
_exptl_absorpt_correction_T_max  0.9873
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10686
_diffrn_reflns_av_R_equivalents  0.1040
_diffrn_reflns_av_sigmaI/netI    0.1043
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.70
_diffrn_reflns_theta_max         25.10
_reflns_number_total             3895
_reflns_number_gt                2198
_reflns_threshold_expression     >2sigma(I)

_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-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3895
_refine_ls_number_parameters     289
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1884
_refine_ls_R_factor_gt           0.1308
_refine_ls_wR_factor_ref         0.4312
_refine_ls_wR_factor_gt          0.3909
_refine_ls_goodness_of_fit_ref   1.448
_refine_ls_restrained_S_all      1.448
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.002

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
C1 C 0.7410(7) 0.3564(3) 0.3040(6) 0.0519(16) Uani 1 1 d . . .
H1 H 0.6679 0.3456 0.3623 0.062 Uiso 1 1 calc R . .
C2 C 0.8796(9) 0.4286(3) 0.2002(8) 0.066(2) Uani 1 1 d . . .
H2 H 0.9009 0.4663 0.1878 0.079 Uiso 1 1 calc R . .
C3 C 0.9640(8) 0.3879(3) 0.1347(7) 0.0602(19) Uani 1 1 d . . .
H3 H 1.0385 0.3986 0.0776 0.072 Uiso 1 1 calc R . .
C4 C 0.9351(7) 0.3330(3) 0.1559(6) 0.0509(16) Uani 1 1 d . . .
H4 H 0.9909 0.3059 0.1134 0.061 Uiso 1 1 calc R . .
C5 C 0.8234(6) 0.3165(3) 0.2401(5) 0.0404(14) Uani 1 1 d . . .
C6 C 0.7948(6) 0.2559(3) 0.2604(5) 0.0431(15) Uani 1 1 d . . .
C7 C 0.8105(6) 0.1632(2) 0.1971(6) 0.0410(14) Uani 1 1 d . . .
C8 C 0.8793(7) 0.1249(3) 0.1161(6) 0.0495(16) Uani 1 1 d . . .
H8 H 0.9223 0.1369 0.0386 0.059 Uiso 1 1 calc R . .
C9 C 0.8840(8) 0.0698(3) 0.1496(7) 0.0621(19) Uani 1 1 d . . .
H9 H 0.9305 0.0445 0.0943 0.075 Uiso 1 1 calc R . .
C10 C 0.8227(9) 0.0510(3) 0.2616(8) 0.070(2) Uani 1 1 d . . .
H10 H 0.8286 0.0132 0.2830 0.084 Uiso 1 1 calc R . .
C11 C 0.7507(8) 0.0878(3) 0.3451(7) 0.0576(18) Uani 1 1 d . . .
H11 H 0.7058 0.0749 0.4209 0.069 Uiso 1 1 calc R . .
C12 C 0.7470(7) 0.1449(3) 0.3130(6) 0.0476(16) Uani 1 1 d . . .
C13 C 0.6745(7) 0.1867(3) 0.3949(6) 0.0489(16) Uani 1 1 d . . .
H13A H 0.5712 0.1902 0.3687 0.059 Uiso 1 1 calc R . .
H13B H 0.6787 0.1751 0.4861 0.059 Uiso 1 1 calc R . .
C14 C 0.2257(8) 0.3544(3) 0.4149(6) 0.0565(17) Uani 1 1 d . . .
H14 H 0.1473 0.3421 0.3623 0.068 Uiso 1 1 calc R . .
C15 C 0.2473(9) 0.4112(3) 0.4334(7) 0.067(2) Uani 1 1 d . . .
H15 H 0.1835 0.4369 0.3940 0.081 Uiso 1 1 calc R . .
C16 C 0.3654(9) 0.4293(3) 0.5117(7) 0.070(2) Uani 1 1 d . . .
H16 H 0.3812 0.4673 0.5253 0.084 Uiso 1 1 calc R . .
C17 C 0.4592(8) 0.3903(3) 0.5690(7) 0.0624(19) Uani 1 1 d . . .
H17 H 0.5391 0.4023 0.6201 0.075 Uiso 1 1 calc R . .
C18 C 0.4362(7) 0.3349(3) 0.5516(6) 0.0539(17) Uani 1 1 d . . .
H18 H 0.4995 0.3094 0.5923 0.065 Uiso 1 1 calc R . .
C19 C 0.3195(6) 0.3156(2) 0.4738(5) 0.0385(14) Uani 1 1 d . . .
C20 C 0.2952(6) 0.2546(2) 0.4550(5) 0.0406(14) Uani 1 1 d . . .
C21 C 0.3177(6) 0.1639(2) 0.5241(6) 0.0424(14) Uani 1 1 d . . .
C22 C 0.3874(6) 0.1263(3) 0.6108(6) 0.0479(16) Uani 1 1 d . . .
H22 H 0.4322 0.1395 0.6875 0.057 Uiso 1 1 calc R . .
C23 C 0.3894(7) 0.0703(3) 0.5824(7) 0.0574(18) Uani 1 1 d . . .
H23 H 0.4300 0.0454 0.6432 0.069 Uiso 1 1 calc R . .
C24 C 0.3333(8) 0.0504(3) 0.4675(8) 0.064(2) Uani 1 1 d . . .
H24 H 0.3411 0.0125 0.4481 0.077 Uiso 1 1 calc R . .
C25 C 0.2651(8) 0.0859(3) 0.3794(7) 0.0590(19) Uani 1 1 d . . .
H25 H 0.2240 0.0719 0.3019 0.071 Uiso 1 1 calc R . .
C26 C 0.2574(6) 0.1432(3) 0.4062(6) 0.0443(15) Uani 1 1 d . . .
C27 C 0.1838(7) 0.1833(3) 0.3173(6) 0.0507(16) Uani 1 1 d . . .
H27A H 0.1938 0.1710 0.2271 0.061 Uiso 1 1 calc R . .
H27B H 0.0790 0.1853 0.3369 0.061 Uiso 1 1 calc R . .
C52 C 0.7680(10) 0.4139(3) 0.2810(8) 0.070(2) Uani 1 1 d . . .
H52 H 0.7101 0.4411 0.3206 0.084 Uiso 1 1 calc R . .
N1 N 0.8157(5) 0.2200(2) 0.1634(5) 0.0428(12) Uani 1 1 d . . .
N2 N 0.7479(6) 0.2397(2) 0.3806(5) 0.0531(15) Uani 1 1 d . . .
H2A H 0.7618 0.2610 0.4477 0.064 Uiso 1 1 calc R . .
N3 N 0.3159(5) 0.2208(2) 0.5535(5) 0.0434(13) Uani 1 1 d . . .
N4 N 0.2504(6) 0.2375(2) 0.3337(5) 0.0512(14) Uani 1 1 d . . .
H4A H 0.2618 0.2590 0.2669 0.061 Uiso 1 1 calc R . .


_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
C1 C5 1.379(8) . ?
C1 C52 1.415(9) . ?
C1 H1 0.9300 . ?
C2 C52 1.355(11) . ?
C2 C3 1.409(10) . ?
C2 H2 0.9300 . ?
C3 C4 1.358(9) . ?
C3 H3 0.9300 . ?
C4 C5 1.388(8) . ?
C4 H4 0.9300 . ?
C5 C6 1.488(8) . ?
C6 N1 1.323(7) . ?
C6 N2 1.356(7) . ?
C7 C8 1.384(8) . ?
C7 C12 1.390(8) . ?
C7 N1 1.403(7) . ?
C8 C9 1.362(9) . ?
C8 H8 0.9300 . ?
C9 C10 1.351(10) . ?
C9 H9 0.9300 . ?
C10 C11 1.391(10) . ?
C10 H10 0.9300 . ?
C11 C12 1.402(9) . ?
C11 H11 0.9300 . ?
C12 C13 1.462(9) . ?
C13 N2 1.438(8) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.384(10) . ?
C14 C19 1.387(8) . ?
C14 H14 0.9300 . ?
C15 C16 1.392(11) . ?
C15 H15 0.9300 . ?
C16 C17 1.384(10) . ?
C16 H16 0.9300 . ?
C17 C18 1.351(9) . ?
C17 H17 0.9300 . ?
C18 C19 1.389(8) . ?
C18 H18 0.9300 . ?
C19 C20 1.487(8) . ?
C20 N3 1.300(7) . ?
C20 N4 1.358(8) . ?
C21 N3 1.394(8) . ?
C21 C26 1.401(8) . ?
C21 C22 1.402(8) . ?
C22 C23 1.372(9) . ?
C22 H22 0.9300 . ?
C23 C24 1.355(10) . ?
C23 H23 0.9300 . ?
C24 C25 1.376(10) . ?
C24 H24 0.9300 . ?
C25 C26 1.398(9) . ?
C25 H25 0.9300 . ?
C26 C27 1.472(9) . ?
C27 N4 1.437(8) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C52 H52 0.9300 . ?
N2 H2A 0.8600 . ?
N4 H4A 0.8600 . ?

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
C5 C1 C52 119.9(6) . . ?
C5 C1 H1 120.1 . . ?
C52 C1 H1 120.1 . . ?
C52 C2 C3 121.2(7) . . ?
C52 C2 H2 119.4 . . ?
C3 C2 H2 119.4 . . ?
C4 C3 C2 119.1(7) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C3 C4 C5 121.0(6) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C1 C5 C4 119.8(6) . . ?
C1 C5 C6 120.9(5) . . ?
C4 C5 C6 119.4(5) . . ?
N1 C6 N2 122.6(6) . . ?
N1 C6 C5 120.0(5) . . ?
N2 C6 C5 117.4(5) . . ?
C8 C7 C12 119.4(6) . . ?
C8 C7 N1 118.6(5) . . ?
C12 C7 N1 121.9(5) . . ?
C9 C8 C7 120.2(6) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C10 C9 C8 121.5(7) . . ?
C10 C9 H9 119.3 . . ?
C8 C9 H9 119.3 . . ?
C9 C10 C11 120.3(7) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C10 C11 C12 119.0(7) . . ?
C10 C11 H11 120.5 . . ?
C12 C11 H11 120.5 . . ?
C7 C12 C11 119.7(6) . . ?
C7 C12 C13 117.5(6) . . ?
C11 C12 C13 122.8(6) . . ?
N2 C13 C12 109.6(5) . . ?
N2 C13 H13A 109.8 . . ?
C12 C13 H13A 109.8 . . ?
N2 C13 H13B 109.8 . . ?
C12 C13 H13B 109.8 . . ?
H13A C13 H13B 108.2 . . ?
C15 C14 C19 120.9(6) . . ?
C15 C14 H14 119.5 . . ?
C19 C14 H14 119.5 . . ?
C14 C15 C16 119.2(7) . . ?
C14 C15 H15 120.4 . . ?
C16 C15 H15 120.4 . . ?
C17 C16 C15 119.4(7) . . ?
C17 C16 H16 120.3 . . ?
C15 C16 H16 120.3 . . ?
C18 C17 C16 120.9(7) . . ?
C18 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?
C17 C18 C19 121.0(6) . . ?
C17 C18 H18 119.5 . . ?
C19 C18 H18 119.5 . . ?
C14 C19 C18 118.6(6) . . ?
C14 C19 C20 120.8(5) . . ?
C18 C19 C20 120.6(5) . . ?
N3 C20 N4 123.6(6) . . ?
N3 C20 C19 119.4(5) . . ?
N4 C20 C19 117.0(5) . . ?
N3 C21 C26 121.5(5) . . ?
N3 C21 C22 119.7(5) . . ?
C26 C21 C22 118.7(6) . . ?
C23 C22 C21 120.0(6) . . ?
C23 C22 H22 120.0 . . ?
C21 C22 H22 120.0 . . ?
C24 C23 C22 121.2(7) . . ?
C24 C23 H23 119.4 . . ?
C22 C23 H23 119.4 . . ?
C23 C24 C25 120.4(7) . . ?
C23 C24 H24 119.8 . . ?
C25 C24 H24 119.8 . . ?
C24 C25 C26 120.0(7) . . ?
C24 C25 H25 120.0 . . ?
C26 C25 H25 120.0 . . ?
C25 C26 C21 119.5(6) . . ?
C25 C26 C27 122.7(6) . . ?
C21 C26 C27 117.7(6) . . ?
N4 C27 C26 109.3(5) . . ?
N4 C27 H27A 109.8 . . ?
C26 C27 H27A 109.8 . . ?
N4 C27 H27B 109.8 . . ?
C26 C27 H27B 109.8 . . ?
H27A C27 H27B 108.3 . . ?
C2 C52 C1 119.0(7) . . ?
C2 C52 H52 120.5 . . ?
C1 C52 H52 120.5 . . ?
C6 N1 C7 116.1(5) . . ?
C6 N2 C13 119.5(5) . . ?
C6 N2 H2A 120.3 . . ?
C13 N2 H2A 120.3 . . ?
C20 N3 C21 116.3(5) . . ?
C20 N4 C27 119.8(5) . . ?
C20 N4 H4A 120.1 . . ?
C27 N4 H4A 120.1 . . ?

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
C52 C2 C3 C4 -1.8(11) . . . . ?
C2 C3 C4 C5 0.5(10) . . . . ?
C52 C1 C5 C4 1.7(9) . . . . ?
C52 C1 C5 C6 -178.6(6) . . . . ?
C3 C4 C5 C1 -0.5(9) . . . . ?
C3 C4 C5 C6 179.8(6) . . . . ?
C1 C5 C6 N1 147.6(6) . . . . ?
C4 C5 C6 N1 -32.7(8) . . . . ?
C1 C5 C6 N2 -32.6(8) . . . . ?
C4 C5 C6 N2 147.1(6) . . . . ?
C12 C7 C8 C9 0.3(9) . . . . ?
N1 C7 C8 C9 176.1(5) . . . . ?
C7 C8 C9 C10 -0.1(10) . . . . ?
C8 C9 C10 C11 0.9(11) . . . . ?
C9 C10 C11 C12 -1.9(11) . . . . ?
C8 C7 C12 C11 -1.3(8) . . . . ?
N1 C7 C12 C11 -177.0(5) . . . . ?
C8 C7 C12 C13 -179.5(5) . . . . ?
N1 C7 C12 C13 4.7(8) . . . . ?
C10 C11 C12 C7 2.1(9) . . . . ?
C10 C11 C12 C13 -179.8(6) . . . . ?
C7 C12 C13 N2 -31.3(7) . . . . ?
C11 C12 C13 N2 150.5(6) . . . . ?
C19 C14 C15 C16 0.4(11) . . . . ?
C14 C15 C16 C17 0.2(11) . . . . ?
C15 C16 C17 C18 -1.0(11) . . . . ?
C16 C17 C18 C19 1.2(11) . . . . ?
C15 C14 C19 C18 -0.2(9) . . . . ?
C15 C14 C19 C20 179.3(6) . . . . ?
C17 C18 C19 C14 -0.6(9) . . . . ?
C17 C18 C19 C20 179.9(6) . . . . ?
C14 C19 C20 N3 -140.7(6) . . . . ?
C18 C19 C20 N3 38.9(8) . . . . ?
C14 C19 C20 N4 38.7(8) . . . . ?
C18 C19 C20 N4 -141.8(6) . . . . ?
N3 C21 C22 C23 179.9(5) . . . . ?
C26 C21 C22 C23 -3.1(8) . . . . ?
C21 C22 C23 C24 4.3(9) . . . . ?
C22 C23 C24 C25 -3.8(10) . . . . ?
C23 C24 C25 C26 2.1(10) . . . . ?
C24 C25 C26 C21 -0.9(9) . . . . ?
C24 C25 C26 C27 -178.9(6) . . . . ?
N3 C21 C26 C25 178.4(5) . . . . ?
C22 C21 C26 C25 1.4(8) . . . . ?
N3 C21 C26 C27 -3.5(8) . . . . ?
C22 C21 C26 C27 179.5(5) . . . . ?
C25 C26 C27 N4 -152.7(6) . . . . ?
C21 C26 C27 N4 29.3(8) . . . . ?
C3 C2 C52 C1 3.0(11) . . . . ?
C5 C1 C52 C2 -2.9(10) . . . . ?
N2 C6 N1 C7 -10.2(8) . . . . ?
C5 C6 N1 C7 169.6(5) . . . . ?
C8 C7 N1 C6 -158.2(5) . . . . ?
C12 C7 N1 C6 17.6(7) . . . . ?
N1 C6 N2 C13 -19.9(9) . . . . ?
C5 C6 N2 C13 160.3(5) . . . . ?
C12 C13 N2 C6 39.6(8) . . . . ?
N4 C20 N3 C21 12.0(8) . . . . ?
C19 C20 N3 C21 -168.7(5) . . . . ?
C26 C21 N3 C20 -18.7(8) . . . . ?
C22 C21 N3 C20 158.2(5) . . . . ?
N3 C20 N4 C27 17.5(9) . . . . ?
C19 C20 N4 C27 -161.8(5) . . . . ?
C26 C27 N4 C20 -36.9(8) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.10
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.534
_refine_diff_density_min         -0.464
_refine_diff_density_rms         0.119
_database_code_depnum_ccdc_archive 'CCDC 977533'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H11 F N2'
_chemical_formula_weight         226.25

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/n  '

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

_cell_length_a                   10.145(6)
_cell_length_b                   9.004(5)
_cell_length_c                   25.125(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.322(10)
_cell_angle_gamma                90.00
_cell_volume                     2258(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2271
_cell_measurement_theta_min      2.80
_cell_measurement_theta_max      25.30

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.23
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             944
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9775
_exptl_absorpt_correction_T_max  0.9792
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7589
_diffrn_reflns_av_R_equivalents  0.0874
_diffrn_reflns_av_sigmaI/netI    0.0903
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.33
_diffrn_reflns_theta_max         25.10
_reflns_number_total             3655
_reflns_number_gt                2360
_reflns_threshold_expression     >2sigma(I)

_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-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.1878P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3655
_refine_ls_number_parameters     307
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1250
_refine_ls_R_factor_gt           0.0778
_refine_ls_wR_factor_ref         0.2920
_refine_ls_wR_factor_gt          0.2388
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_restrained_S_all      1.090
_refine_ls_shift/su_max          0.002
_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
C1 C 0.6678(4) 0.5626(4) 0.16655(16) 0.0458(10) Uani 1 1 d . . .
H1 H 0.7195 0.5026 0.1923 0.055 Uiso 1 1 calc R . .
C2 C 0.6692(4) 0.5389(5) 0.11262(16) 0.0532(11) Uani 1 1 d . . .
H2 H 0.7203 0.4627 0.1017 0.064 Uiso 1 1 calc R . .
C3 C 0.5942(5) 0.6294(5) 0.07546(17) 0.0575(12) Uani 1 1 d . . .
C4 C 0.5142(5) 0.7398(5) 0.0898(2) 0.0647(13) Uani 1 1 d . . .
H4 H 0.4624 0.7983 0.0636 0.078 Uiso 1 1 calc R . .
C5 C 0.5122(4) 0.7620(5) 0.14380(18) 0.0556(12) Uani 1 1 d . . .
H5 H 0.4581 0.8361 0.1542 0.067 Uiso 1 1 calc R . .
C6 C 0.5904(4) 0.6746(4) 0.18314(15) 0.0383(9) Uani 1 1 d . . .
C7 C 0.5937(4) 0.7034(4) 0.24137(15) 0.0354(9) Uani 1 1 d . . .
C8 C 0.4857(4) 0.8232(4) 0.30756(15) 0.0500(11) Uani 1 1 d . . .
H8A H 0.3989 0.8203 0.3185 0.060 Uiso 1 1 calc R . .
H8B H 0.5103 0.9264 0.3041 0.060 Uiso 1 1 calc R . .
C9 C 0.5885(4) 0.7478(4) 0.34956(16) 0.0422(10) Uani 1 1 d . . .
C10 C 0.5814(5) 0.7363(5) 0.40323(17) 0.0555(12) Uani 1 1 d . . .
H10 H 0.5068 0.7742 0.4154 0.067 Uiso 1 1 calc R . .
C11 C 0.6805(6) 0.6707(5) 0.43951(19) 0.0674(14) Uani 1 1 d . . .
H11 H 0.6751 0.6668 0.4760 0.081 Uiso 1 1 calc R . .
C12 C 0.7897(5) 0.6098(5) 0.42092(17) 0.0621(13) Uani 1 1 d . . .
H12 H 0.8574 0.5640 0.4452 0.075 Uiso 1 1 calc R . .
C13 C 0.7986(4) 0.6165(4) 0.36701(16) 0.0471(10) Uani 1 1 d . . .
H13 H 0.8716 0.5744 0.3550 0.057 Uiso 1 1 calc R . .
C14 C 0.6979(4) 0.6866(4) 0.33032(14) 0.0365(9) Uani 1 1 d . . .
C15 C 0.2282(4) 0.5632(4) 0.32568(15) 0.0418(10) Uani 1 1 d . . .
H15 H 0.2607 0.5024 0.3010 0.050 Uiso 1 1 calc R . .
C16 C 0.2691(4) 0.5404(4) 0.38015(16) 0.0493(11) Uani 1 1 d . . .
H16 H 0.3285 0.4642 0.3927 0.059 Uiso 1 1 calc R . .
C17 C 0.2212(5) 0.6311(5) 0.41528(15) 0.0533(12) Uani 1 1 d . . .
C18 C 0.1336(5) 0.7429(5) 0.39915(17) 0.0564(12) Uani 1 1 d . . .
H18 H 0.1025 0.8030 0.4243 0.068 Uiso 1 1 calc R . .
C19 C 0.0921(4) 0.7650(4) 0.34465(16) 0.0481(11) Uani 1 1 d . . .
H19 H 0.0317 0.8408 0.3328 0.058 Uiso 1 1 calc R . .
C20 C 0.1384(4) 0.6765(4) 0.30707(14) 0.0351(9) Uani 1 1 d . . .
C21 C 0.0964(4) 0.7035(4) 0.24820(15) 0.0362(9) Uani 1 1 d . . .
C22 C -0.0670(4) 0.8218(4) 0.17945(15) 0.0468(10) Uani 1 1 d . . .
H22A H -0.0387 0.9249 0.1825 0.056 Uiso 1 1 calc R . .
H22B H -0.1633 0.8194 0.1675 0.056 Uiso 1 1 calc R . .
C23 C 0.0002(4) 0.7441(4) 0.13949(15) 0.0407(10) Uani 1 1 d . . .
C24 C -0.0495(5) 0.7363(5) 0.08511(17) 0.0578(12) Uani 1 1 d . . .
H24 H -0.1327 0.7781 0.0718 0.069 Uiso 1 1 calc R . .
C25 C 0.0205(5) 0.6681(6) 0.04966(18) 0.0679(14) Uani 1 1 d . . .
H25 H -0.0144 0.6647 0.0128 0.081 Uiso 1 1 calc R . .
C26 C 0.1434(6) 0.6051(5) 0.06985(18) 0.0644(13) Uani 1 1 d . . .
H26 H 0.1916 0.5581 0.0465 0.077 Uiso 1 1 calc R . .
C27 C 0.1947(4) 0.6114(4) 0.12435(16) 0.0479(10) Uani 1 1 d . . .
H27 H 0.2775 0.5684 0.1375 0.057 Uiso 1 1 calc R . .
C28 C 0.1253(4) 0.6806(4) 0.15966(14) 0.0368(9) Uani 1 1 d . . .
F1 F 0.6001(4) 0.6093(4) 0.02217(10) 0.0942(11) Uani 1 1 d . . .
F2 F 0.2620(3) 0.6070(3) 0.46934(10) 0.0880(10) Uani 1 1 d . . .
N1 N 0.4786(3) 0.7490(4) 0.25657(13) 0.0462(9) Uani 1 1 d . . .
H1A H 0.4025 0.7337 0.2360 0.055 Uiso 1 1 calc R . .
N2 N 0.7069(3) 0.6846(3) 0.27473(12) 0.0375(8) Uani 1 1 d . . .
N3 N -0.0319(3) 0.7489(3) 0.23172(13) 0.0429(8) Uani 1 1 d . . .
H3 H -0.0912 0.7350 0.2517 0.052 Uiso 1 1 calc R . .
N4 N 0.1798(3) 0.6800(3) 0.21560(12) 0.0346(8) Uani 1 1 d . . .


_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
C1 C2 1.374(5) . ?
C1 C6 1.388(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.364(6) . ?
C2 H2 0.9300 . ?
C3 F1 1.363(5) . ?
C3 C4 1.372(7) . ?
C4 C5 1.375(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.394(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.480(5) . ?
C7 N2 1.306(5) . ?
C7 N1 1.355(5) . ?
C8 N1 1.435(5) . ?
C8 C9 1.506(6) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.367(6) . ?
C9 C14 1.401(5) . ?
C10 C11 1.365(7) . ?
C10 H10 0.9300 . ?
C11 C12 1.390(7) . ?
C11 H11 0.9300 . ?
C12 C13 1.375(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.398(5) . ?
C13 H13 0.9300 . ?
C14 N2 1.416(4) . ?
C15 C16 1.373(5) . ?
C15 C20 1.392(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.355(6) . ?
C16 H16 0.9300 . ?
C17 C18 1.355(6) . ?
C17 F2 1.364(4) . ?
C18 C19 1.373(6) . ?
C18 H18 0.9300 . ?
C19 C20 1.380(5) . ?
C19 H19 0.9300 . ?
C20 C21 1.484(5) . ?
C21 N4 1.296(5) . ?
C21 N3 1.356(5) . ?
C22 N3 1.454(5) . ?
C22 C23 1.486(5) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 C24 1.371(5) . ?
C23 C28 1.401(6) . ?
C24 C25 1.378(7) . ?
C24 H24 0.9300 . ?
C25 C26 1.381(7) . ?
C25 H25 0.9300 . ?
C26 C27 1.376(6) . ?
C26 H26 0.9300 . ?
C27 C28 1.377(5) . ?
C27 H27 0.9300 . ?
C28 N4 1.415(4) . ?
N1 H1A 0.8600 . ?
N3 H3 0.8600 . ?

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
C2 C1 C6 121.0(4) . . ?
C2 C1 H1 119.5 . . ?
C6 C1 H1 119.5 . . ?
C3 C2 C1 118.6(4) . . ?
C3 C2 H2 120.7 . . ?
C1 C2 H2 120.7 . . ?
F1 C3 C2 118.4(4) . . ?
F1 C3 C4 119.1(4) . . ?
C2 C3 C4 122.4(4) . . ?
C3 C4 C5 118.7(4) . . ?
C3 C4 H4 120.7 . . ?
C5 C4 H4 120.7 . . ?
C4 C5 C6 120.6(4) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 118.6(4) . . ?
C1 C6 C7 120.7(3) . . ?
C5 C6 C7 120.7(4) . . ?
N2 C7 N1 124.2(4) . . ?
N2 C7 C6 118.2(3) . . ?
N1 C7 C6 117.6(3) . . ?
N1 C8 C9 109.5(3) . . ?
N1 C8 H8A 109.8 . . ?
C9 C8 H8A 109.8 . . ?
N1 C8 H8B 109.8 . . ?
C9 C8 H8B 109.8 . . ?
H8A C8 H8B 108.2 . . ?
C10 C9 C14 119.7(4) . . ?
C10 C9 C8 125.0(4) . . ?
C14 C9 C8 115.3(3) . . ?
C11 C10 C9 121.9(4) . . ?
C11 C10 H10 119.0 . . ?
C9 C10 H10 119.0 . . ?
C10 C11 C12 118.8(4) . . ?
C10 C11 H11 120.6 . . ?
C12 C11 H11 120.6 . . ?
C13 C12 C11 120.7(4) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C12 C13 C14 120.0(4) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C13 C14 C9 118.7(4) . . ?
C13 C14 N2 118.4(3) . . ?
C9 C14 N2 122.7(3) . . ?
C16 C15 C20 120.5(3) . . ?
C16 C15 H15 119.8 . . ?
C20 C15 H15 119.8 . . ?
C17 C16 C15 118.7(4) . . ?
C17 C16 H16 120.7 . . ?
C15 C16 H16 120.7 . . ?
C16 C17 C18 123.0(4) . . ?
C16 C17 F2 118.2(4) . . ?
C18 C17 F2 118.8(4) . . ?
C17 C18 C19 118.3(4) . . ?
C17 C18 H18 120.9 . . ?
C19 C18 H18 120.9 . . ?
C18 C19 C20 121.2(4) . . ?
C18 C19 H19 119.4 . . ?
C20 C19 H19 119.4 . . ?
C19 C20 C15 118.4(4) . . ?
C19 C20 C21 121.0(3) . . ?
C15 C20 C21 120.6(3) . . ?
N4 C21 N3 123.8(3) . . ?
N4 C21 C20 120.0(3) . . ?
N3 C21 C20 116.3(3) . . ?
N3 C22 C23 109.3(3) . . ?
N3 C22 H22A 109.8 . . ?
C23 C22 H22A 109.8 . . ?
N3 C22 H22B 109.8 . . ?
C23 C22 H22B 109.8 . . ?
H22A C22 H22B 108.3 . . ?
C24 C23 C28 119.2(4) . . ?
C24 C23 C22 124.5(4) . . ?
C28 C23 C22 116.3(3) . . ?
C23 C24 C25 121.8(4) . . ?
C23 C24 H24 119.1 . . ?
C25 C24 H24 119.1 . . ?
C24 C25 C26 118.8(4) . . ?
C24 C25 H25 120.6 . . ?
C26 C25 H25 120.6 . . ?
C27 C26 C25 120.3(5) . . ?
C27 C26 H26 119.9 . . ?
C25 C26 H26 119.9 . . ?
C26 C27 C28 120.9(4) . . ?
C26 C27 H27 119.6 . . ?
C28 C27 H27 119.6 . . ?
C27 C28 C23 119.1(4) . . ?
C27 C28 N4 119.0(4) . . ?
C23 C28 N4 121.9(3) . . ?
C7 N1 C8 119.0(3) . . ?
C7 N1 H1A 120.5 . . ?
C8 N1 H1A 120.5 . . ?
C7 N2 C14 115.3(3) . . ?
C21 N3 C22 118.6(3) . . ?
C21 N3 H3 120.7 . . ?
C22 N3 H3 120.7 . . ?
C21 N4 C28 116.3(3) . . ?

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
C6 C1 C2 C3 0.9(6) . . . . ?
C1 C2 C3 F1 177.4(3) . . . . ?
C1 C2 C3 C4 -2.2(6) . . . . ?
F1 C3 C4 C5 -178.0(4) . . . . ?
C2 C3 C4 C5 1.5(7) . . . . ?
C3 C4 C5 C6 0.3(6) . . . . ?
C2 C1 C6 C5 0.8(5) . . . . ?
C2 C1 C6 C7 -177.5(3) . . . . ?
C4 C5 C6 C1 -1.5(6) . . . . ?
C4 C5 C6 C7 176.9(4) . . . . ?
C1 C6 C7 N2 34.7(5) . . . . ?
C5 C6 C7 N2 -143.6(4) . . . . ?
C1 C6 C7 N1 -145.9(4) . . . . ?
C5 C6 C7 N1 35.8(5) . . . . ?
N1 C8 C9 C10 -147.4(4) . . . . ?
N1 C8 C9 C14 32.7(5) . . . . ?
C14 C9 C10 C11 2.2(6) . . . . ?
C8 C9 C10 C11 -177.7(4) . . . . ?
C9 C10 C11 C12 -2.1(7) . . . . ?
C10 C11 C12 C13 0.6(7) . . . . ?
C11 C12 C13 C14 0.7(6) . . . . ?
C12 C13 C14 C9 -0.6(5) . . . . ?
C12 C13 C14 N2 -176.8(3) . . . . ?
C10 C9 C14 C13 -0.8(5) . . . . ?
C8 C9 C14 C13 179.1(3) . . . . ?
C10 C9 C14 N2 175.2(3) . . . . ?
C8 C9 C14 N2 -4.9(5) . . . . ?
C20 C15 C16 C17 -0.6(6) . . . . ?
C15 C16 C17 C18 0.6(7) . . . . ?
C15 C16 C17 F2 179.7(3) . . . . ?
C16 C17 C18 C19 -0.2(7) . . . . ?
F2 C17 C18 C19 -179.2(4) . . . . ?
C17 C18 C19 C20 -0.3(6) . . . . ?
C18 C19 C20 C15 0.3(6) . . . . ?
C18 C19 C20 C21 -178.2(3) . . . . ?
C16 C15 C20 C19 0.1(5) . . . . ?
C16 C15 C20 C21 178.6(3) . . . . ?
C19 C20 C21 N4 145.2(4) . . . . ?
C15 C20 C21 N4 -33.3(5) . . . . ?
C19 C20 C21 N3 -36.4(5) . . . . ?
C15 C20 C21 N3 145.1(3) . . . . ?
N3 C22 C23 C24 150.4(4) . . . . ?
N3 C22 C23 C28 -32.2(4) . . . . ?
C28 C23 C24 C25 -0.3(6) . . . . ?
C22 C23 C24 C25 177.0(4) . . . . ?
C23 C24 C25 C26 0.6(7) . . . . ?
C24 C25 C26 C27 -0.4(7) . . . . ?
C25 C26 C27 C28 -0.1(6) . . . . ?
C26 C27 C28 C23 0.5(5) . . . . ?
C26 C27 C28 N4 177.9(3) . . . . ?
C24 C23 C28 C27 -0.3(5) . . . . ?
C22 C23 C28 C27 -177.8(3) . . . . ?
C24 C23 C28 N4 -177.6(3) . . . . ?
C22 C23 C28 N4 4.9(4) . . . . ?
N2 C7 N1 C8 19.5(5) . . . . ?
C6 C7 N1 C8 -159.9(3) . . . . ?
C9 C8 N1 C7 -40.9(5) . . . . ?
N1 C7 N2 C14 12.0(5) . . . . ?
C6 C7 N2 C14 -168.7(3) . . . . ?
C13 C14 N2 C7 157.2(3) . . . . ?
C9 C14 N2 C7 -18.8(4) . . . . ?
N4 C21 N3 C22 -21.2(5) . . . . ?
C20 C21 N3 C22 160.5(3) . . . . ?
C23 C22 N3 C21 41.1(4) . . . . ?
N3 C21 N4 C28 -10.0(5) . . . . ?
C20 C21 N4 C28 168.3(3) . . . . ?
C27 C28 N4 C21 -159.3(3) . . . . ?
C23 C28 N4 C21 18.0(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.910
_diffrn_reflns_theta_full        25.10
_diffrn_measured_fraction_theta_full 0.910
_refine_diff_density_max         0.648
_refine_diff_density_min         -0.448
_refine_diff_density_rms         0.169
_database_code_depnum_ccdc_archive 'CCDC 977534'
