# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2015

####################################################################### 
# 
# 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_vas12
_database_code_depnum_ccdc_archive 'CCDC 1007197'
_audit_update_record             
;
2014-06-07 deposited with the CCDC.
2015-04-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H14 N2'
_chemical_formula_sum            'C21 H14 N2'
_chemical_formula_weight         294.34

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   P2(1)/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                   12.8102(3)
_cell_length_b                   12.3291(3)
_cell_length_c                   10.2865(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 112.0070(10)
_cell_angle_gamma                90.00
_cell_volume                     1506.26(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1132
_cell_measurement_theta_min      3.41
_cell_measurement_theta_max      27.32

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             616
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9575
_exptl_absorpt_correction_T_max  0.9947
_exptl_absorpt_process_details   'SADABS (Bruker, 2006)'

_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  'CCD Area Detector'
_diffrn_measurement_device       'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9838
_diffrn_reflns_av_R_equivalents  0.0984
_diffrn_reflns_av_sigmaI/netI    0.0888
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.70
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2633
_reflns_number_gt                1734
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2006)'
_computing_cell_refinement       'APEX2 (Bruker, 2006)'
_computing_data_reduction        'APEX2 (Bruker, 2006)'
_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)+(0.1653P)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         2633
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1088
_refine_ls_R_factor_gt           0.0809
_refine_ls_wR_factor_ref         0.2479
_refine_ls_wR_factor_gt          0.2133
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      1.000
_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
N1 N 0.0765(2) 0.2239(2) -0.1568(2) 0.0378(7) Uani 1 1 d . . .
N2 N 0.0742(2) 0.2236(2) 0.0592(3) 0.0398(7) Uani 1 1 d . . .
H2N H 0.0944 0.2367 0.1474 0.048 Uiso 1 1 calc R . .
C1 C -0.0162(2) 0.1652(2) -0.1575(3) 0.0356(7) Uani 1 1 d . . .
C2 C -0.0991(3) 0.1109(3) -0.2666(3) 0.0450(8) Uani 1 1 d . . .
H2 H -0.0989 0.1114 -0.3569 0.054 Uiso 1 1 calc R . .
C3 C -0.1809(3) 0.0567(3) -0.2370(4) 0.0523(9) Uani 1 1 d . . .
H3 H -0.2362 0.0191 -0.3082 0.063 Uiso 1 1 calc R . .
C4 C -0.1832(3) 0.0567(3) -0.1014(4) 0.0545(9) Uani 1 1 d . . .
H4 H -0.2402 0.0197 -0.0846 0.065 Uiso 1 1 calc R . .
C5 C -0.1023(3) 0.1108(3) 0.0067(3) 0.0513(9) Uani 1 1 d . . .
H5 H -0.1035 0.1114 0.0965 0.062 Uiso 1 1 calc R . .
C6 C -0.0188(2) 0.1644(2) -0.0229(3) 0.0375(7) Uani 1 1 d . . .
C7 C 0.1281(3) 0.2574(2) -0.0256(3) 0.0371(7) Uani 1 1 d . . .
C8 C 0.2331(2) 0.3209(2) 0.0251(3) 0.0353(7) Uani 1 1 d . . .
C9 C 0.2356(2) 0.4240(3) 0.0842(3) 0.0369(7) Uani 1 1 d . . .
C10 C 0.1396(3) 0.4711(3) 0.1022(3) 0.0406(8) Uani 1 1 d . . .
H10 H 0.0730 0.4318 0.0773 0.049 Uiso 1 1 calc R . .
C11 C 0.1451(3) 0.5728(3) 0.1554(3) 0.0502(9) Uani 1 1 d . . .
H11 H 0.0818 0.6022 0.1656 0.060 Uiso 1 1 calc R . .
C12 C 0.2436(3) 0.6338(3) 0.1949(4) 0.0554(10) Uani 1 1 d . . .
H12 H 0.2456 0.7031 0.2314 0.066 Uiso 1 1 calc R . .
C13 C 0.3365(3) 0.5925(3) 0.1803(3) 0.0533(9) Uani 1 1 d . . .
H13 H 0.4018 0.6341 0.2072 0.064 Uiso 1 1 calc R . .
C14 C 0.3361(3) 0.4874(3) 0.1250(3) 0.0427(8) Uani 1 1 d . . .
C15 C 0.4310(3) 0.4446(3) 0.1096(3) 0.0464(8) Uani 1 1 d . . .
H15 H 0.4965 0.4858 0.1374 0.056 Uiso 1 1 calc R . .
C16 C 0.4309(3) 0.3423(3) 0.0540(3) 0.0438(8) Uani 1 1 d . . .
C17 C 0.5283(3) 0.2985(3) 0.0386(4) 0.0539(9) Uani 1 1 d . . .
H17 H 0.5942 0.3392 0.0663 0.065 Uiso 1 1 calc R . .
C18 C 0.5262(3) 0.1984(3) -0.0158(4) 0.0600(10) Uani 1 1 d . . .
H18 H 0.5904 0.1713 -0.0262 0.072 Uiso 1 1 calc R . .
C19 C 0.4288(3) 0.1355(3) -0.0566(4) 0.0545(9) Uani 1 1 d . . .
H19 H 0.4293 0.0664 -0.0926 0.065 Uiso 1 1 calc R . .
C20 C 0.3337(3) 0.1730(3) -0.0446(3) 0.0460(8) Uani 1 1 d . . .
H20 H 0.2698 0.1294 -0.0726 0.055 Uiso 1 1 calc R . .
C21 C 0.3300(3) 0.2779(3) 0.0101(3) 0.0393(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
N1 C7 1.327(5) . ?
N1 C1 1.389(4) . ?
N2 C7 1.364(4) . ?
N2 C6 1.383(4) . ?
N2 H2N 0.8600 . ?
C1 C2 1.394(4) . ?
C1 C6 1.397(5) . ?
C2 C3 1.370(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.406(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.376(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.384(4) . ?
C5 H5 0.9300 . ?
C7 C8 1.473(4) . ?
C8 C9 1.405(4) . ?
C8 C21 1.410(4) . ?
C9 C14 1.429(4) . ?
C9 C10 1.432(4) . ?
C10 C11 1.359(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.393(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.352(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.415(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.387(4) . ?
C15 C16 1.385(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.422(4) . ?
C16 C21 1.438(4) . ?
C17 C18 1.351(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.394(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.352(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.419(4) . ?
C20 H20 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 N1 C1 105.5(2) . . ?
C7 N2 C6 107.3(3) . . ?
C7 N2 H2N 126.3 . . ?
C6 N2 H2N 126.3 . . ?
N1 C1 C2 130.3(3) . . ?
N1 C1 C6 109.7(3) . . ?
C2 C1 C6 120.1(3) . . ?
C3 C2 C1 118.0(3) . . ?
C3 C2 H2 121.0 . . ?
C1 C2 H2 121.0 . . ?
C2 C3 C4 121.5(3) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
C5 C4 C3 120.8(3) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 117.7(3) . . ?
C4 C5 H5 121.2 . . ?
C6 C5 H5 121.2 . . ?
N2 C6 C5 132.7(3) . . ?
N2 C6 C1 105.5(3) . . ?
C5 C6 C1 121.9(3) . . ?
N1 C7 N2 112.1(3) . . ?
N1 C7 C8 124.5(2) . . ?
N2 C7 C8 123.4(3) . . ?
C9 C8 C21 120.6(3) . . ?
C9 C8 C7 120.2(3) . . ?
C21 C8 C7 119.1(3) . . ?
C8 C9 C14 119.6(3) . . ?
C8 C9 C10 122.8(3) . . ?
C14 C9 C10 117.6(3) . . ?
C11 C10 C9 120.6(3) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C10 C11 C12 121.3(3) . . ?
C10 C11 H11 119.3 . . ?
C12 C11 H11 119.3 . . ?
C13 C12 C11 120.2(3) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C12 C13 C14 121.2(3) . . ?
C12 C13 H13 119.4 . . ?
C14 C13 H13 119.4 . . ?
C15 C14 C13 121.6(3) . . ?
C15 C14 C9 119.4(3) . . ?
C13 C14 C9 119.1(3) . . ?
C16 C15 C14 121.9(3) . . ?
C16 C15 H15 119.0 . . ?
C14 C15 H15 119.0 . . ?
C15 C16 C17 121.8(3) . . ?
C15 C16 C21 119.6(3) . . ?
C17 C16 C21 118.6(3) . . ?
C18 C17 C16 120.8(3) . . ?
C18 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?
C17 C18 C19 120.6(3) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 H18 119.7 . . ?
C20 C19 C18 121.2(3) . . ?
C20 C19 H19 119.4 . . ?
C18 C19 H19 119.4 . . ?
C19 C20 C21 120.9(3) . . ?
C19 C20 H20 119.6 . . ?
C21 C20 H20 119.6 . . ?
C8 C21 C20 123.2(3) . . ?
C8 C21 C16 118.9(3) . . ?
C20 C21 C16 117.9(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
C7 N1 C1 C2 -179.4(3) . . . . ?
C7 N1 C1 C6 0.0(3) . . . . ?
N1 C1 C2 C3 178.6(3) . . . . ?
C6 C1 C2 C3 -0.7(5) . . . . ?
C1 C2 C3 C4 1.0(5) . . . . ?
C2 C3 C4 C5 -0.5(6) . . . . ?
C3 C4 C5 C6 -0.3(5) . . . . ?
C7 N2 C6 C5 179.5(3) . . . . ?
C7 N2 C6 C1 0.1(3) . . . . ?
C4 C5 C6 N2 -178.7(3) . . . . ?
C4 C5 C6 C1 0.6(5) . . . . ?
N1 C1 C6 N2 -0.1(3) . . . . ?
C2 C1 C6 N2 179.4(3) . . . . ?
N1 C1 C6 C5 -179.6(3) . . . . ?
C2 C1 C6 C5 -0.1(5) . . . . ?
C1 N1 C7 N2 0.1(3) . . . . ?
C1 N1 C7 C8 178.3(3) . . . . ?
C6 N2 C7 N1 -0.1(3) . . . . ?
C6 N2 C7 C8 -178.4(3) . . . . ?
N1 C7 C8 C9 120.2(3) . . . . ?
N2 C7 C8 C9 -61.7(4) . . . . ?
N1 C7 C8 C21 -58.1(4) . . . . ?
N2 C7 C8 C21 120.0(3) . . . . ?
C21 C8 C9 C14 2.1(4) . . . . ?
C7 C8 C9 C14 -176.2(3) . . . . ?
C21 C8 C9 C10 -179.8(3) . . . . ?
C7 C8 C9 C10 1.9(4) . . . . ?
C8 C9 C10 C11 -177.7(3) . . . . ?
C14 C9 C10 C11 0.4(4) . . . . ?
C9 C10 C11 C12 -0.5(5) . . . . ?
C10 C11 C12 C13 0.3(5) . . . . ?
C11 C12 C13 C14 0.1(5) . . . . ?
C12 C13 C14 C15 179.9(3) . . . . ?
C12 C13 C14 C9 -0.1(5) . . . . ?
C8 C9 C14 C15 -2.0(4) . . . . ?
C10 C9 C14 C15 179.8(3) . . . . ?
C8 C9 C14 C13 178.1(3) . . . . ?
C10 C9 C14 C13 -0.1(4) . . . . ?
C13 C14 C15 C16 -179.3(3) . . . . ?
C9 C14 C15 C16 0.8(5) . . . . ?
C14 C15 C16 C17 -179.9(3) . . . . ?
C14 C15 C16 C21 0.3(5) . . . . ?
C15 C16 C17 C18 180.0(3) . . . . ?
C21 C16 C17 C18 -0.2(5) . . . . ?
C16 C17 C18 C19 -0.7(5) . . . . ?
C17 C18 C19 C20 0.9(5) . . . . ?
C18 C19 C20 C21 -0.1(5) . . . . ?
C9 C8 C21 C20 177.9(3) . . . . ?
C7 C8 C21 C20 -3.7(4) . . . . ?
C9 C8 C21 C16 -1.1(4) . . . . ?
C7 C8 C21 C16 177.2(2) . . . . ?
C19 C20 C21 C8 -179.9(3) . . . . ?
C19 C20 C21 C16 -0.8(5) . . . . ?
C15 C16 C21 C8 -0.1(4) . . . . ?
C17 C16 C21 C8 -180.0(3) . . . . ?
C15 C16 C21 C20 -179.2(3) . . . . ?
C17 C16 C21 C20 0.9(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.327
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.081
