# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 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_c

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H14 N2'
_chemical_formula_weight         306.35

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           ?
_symmetry_space_group_name_H-M   ?

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                   9.1083(18)
_cell_length_b                   9.872(2)
_cell_length_c                   16.583(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.24(3)
_cell_angle_gamma                90.00
_cell_volume                     1462.5(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             640
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13871
_diffrn_reflns_av_R_equivalents  0.0717
_diffrn_reflns_av_sigmaI/netI    0.0669
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.08
_diffrn_reflns_theta_max         27.48
_reflns_number_total             3340
_reflns_number_gt                2240
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0693P)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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3340
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0810
_refine_ls_R_factor_gt           0.0526
_refine_ls_wR_factor_ref         0.1342
_refine_ls_wR_factor_gt          0.1222
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.003
_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
N2 N 0.72652(15) 1.05457(16) 0.18946(8) 0.0309(4) Uani 1 1 d . . .
H2B H 0.6603 1.1171 0.1880 0.037 Uiso 1 1 calc R . .
N1 N 0.61774(15) 1.12085(15) 0.00176(8) 0.0306(4) Uani 1 1 d . . .
H1B H 0.5686 1.1749 0.0274 0.037 Uiso 1 1 calc R . .
C1 C 0.62802(19) 1.0745(2) -0.24343(11) 0.0356(4) Uani 1 1 d . . .
H1A H 0.6340 1.0616 -0.2983 0.043 Uiso 1 1 calc R . .
C2 C 1.10744(19) 0.6530(2) 0.04996(12) 0.0371(5) Uani 1 1 d . . .
H2A H 1.1810 0.5878 0.0658 0.044 Uiso 1 1 calc R . .
C3 C 0.5339(2) 1.1754(2) -0.22274(11) 0.0372(4) Uani 1 1 d . . .
H3A H 0.4782 1.2284 -0.2640 0.045 Uiso 1 1 calc R . .
C4 C 1.05241(19) 0.6771(2) -0.03326(12) 0.0386(5) Uani 1 1 d . . .
H4A H 1.0889 0.6275 -0.0728 0.046 Uiso 1 1 calc R . .
C5 C 0.8935(2) 0.9473(2) 0.40123(11) 0.0367(5) Uani 1 1 d . . .
H5A H 0.8871 0.9581 0.4562 0.044 Uiso 1 1 calc R . .
C6 C 0.71238(19) 0.99363(19) -0.18355(10) 0.0317(4) Uani 1 1 d . . .
H6A H 0.7749 0.9273 -0.1981 0.038 Uiso 1 1 calc R . .
C7 C 0.77060(17) 0.99782(18) 0.12217(10) 0.0274(4) Uani 1 1 d . . .
C8 C 0.88708(17) 0.85131(18) 0.00147(10) 0.0271(4) Uani 1 1 d . . .
C9 C 0.52263(19) 1.1970(2) -0.14247(11) 0.0356(4) Uani 1 1 d . . .
H9A H 0.4604 1.2643 -0.1287 0.043 Uiso 1 1 calc R . .
C10 C 1.01162(18) 0.8379(2) 0.29942(11) 0.0329(4) Uani 1 1 d . . .
H10A H 1.0837 0.7792 0.2867 0.040 Uiso 1 1 calc R . .
C11 C 1.00388(19) 0.8628(2) 0.38076(11) 0.0364(5) Uani 1 1 d . . .
H11A H 1.0733 0.8225 0.4224 0.044 Uiso 1 1 calc R . .
C12 C 1.05333(18) 0.72533(19) 0.10864(11) 0.0326(4) Uani 1 1 d . . .
H12A H 1.0904 0.7075 0.1639 0.039 Uiso 1 1 calc R . .
C13 C 0.94456(18) 0.77385(19) -0.05706(11) 0.0337(4) Uani 1 1 d . . .
H13A H 0.9085 0.7888 -0.1128 0.040 Uiso 1 1 calc R . .
C14 C 0.71992(17) 1.02556(18) 0.03781(10) 0.0275(4) Uani 1 1 d . . .
C15 C 0.60710(18) 1.11545(18) -0.08217(10) 0.0294(4) Uani 1 1 d . . .
C16 C 0.79358(19) 1.0152(2) 0.34129(11) 0.0342(4) Uani 1 1 d . . .
H16A H 0.7209 1.0723 0.3549 0.041 Uiso 1 1 calc R . .
C17 C 0.90987(18) 0.90183(18) 0.23624(10) 0.0288(4) Uani 1 1 d . . .
C18 C 0.80613(18) 0.99462(18) 0.25963(10) 0.0289(4) Uani 1 1 d . . .
C19 C 0.77591(17) 0.95488(17) -0.02195(10) 0.0262(4) Uani 1 1 d . . .
C20 C 0.70307(17) 1.01234(18) -0.10026(10) 0.0275(4) Uani 1 1 d . . .
C21 C 0.94298(16) 0.82579(18) 0.08694(10) 0.0275(4) Uani 1 1 d . . .
C22 C 0.88319(17) 0.90221(18) 0.14696(10) 0.0276(4) 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
N2 C7 1.376(2) . ?
N2 C18 1.379(2) . ?
N1 C14 1.375(2) . ?
N1 C15 1.377(2) . ?
C1 C6 1.384(3) . ?
C1 C3 1.400(3) . ?
C2 C12 1.373(3) . ?
C2 C4 1.394(3) . ?
C3 C9 1.372(3) . ?
C4 C13 1.372(3) . ?
C5 C16 1.383(3) . ?
C5 C11 1.399(3) . ?
C6 C20 1.412(2) . ?
C7 C22 1.395(2) . ?
C7 C14 1.412(2) . ?
C8 C13 1.414(2) . ?
C8 C21 1.432(2) . ?
C8 C19 1.438(2) . ?
C9 C15 1.393(2) . ?
C10 C11 1.386(2) . ?
C10 C17 1.406(2) . ?
C12 C21 1.408(2) . ?
C14 C19 1.388(2) . ?
C15 C20 1.411(2) . ?
C16 C18 1.396(2) . ?
C17 C18 1.423(2) . ?
C17 C22 1.453(2) . ?
C19 C20 1.453(2) . ?
C21 C22 1.438(2) . ?

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 N2 C18 108.72(14) . . ?
C14 N1 C15 108.74(14) . . ?
C6 C1 C3 121.02(17) . . ?
C12 C2 C4 120.22(17) . . ?
C9 C3 C1 120.94(17) . . ?
C13 C4 C2 120.19(18) . . ?
C16 C5 C11 121.22(17) . . ?
C1 C6 C20 119.69(17) . . ?
N2 C7 C22 110.49(15) . . ?
N2 C7 C14 129.32(16) . . ?
C22 C7 C14 120.18(16) . . ?
C13 C8 C21 118.46(16) . . ?
C13 C8 C19 122.32(16) . . ?
C21 C8 C19 119.22(15) . . ?
C3 C9 C15 118.10(18) . . ?
C11 C10 C17 119.63(17) . . ?
C10 C11 C5 121.14(17) . . ?
C2 C12 C21 121.46(17) . . ?
C4 C13 C8 121.28(17) . . ?
N1 C14 C19 110.19(14) . . ?
N1 C14 C7 128.77(16) . . ?
C19 C14 C7 121.02(15) . . ?
N1 C15 C9 128.55(17) . . ?
N1 C15 C20 108.55(15) . . ?
C9 C15 C20 122.87(17) . . ?
C5 C16 C18 117.38(18) . . ?
C10 C17 C18 117.53(16) . . ?
C10 C17 C22 135.69(17) . . ?
C18 C17 C22 106.74(14) . . ?
N2 C18 C16 128.84(17) . . ?
N2 C18 C17 108.31(15) . . ?
C16 C18 C17 122.85(16) . . ?
C14 C19 C8 120.13(15) . . ?
C14 C19 C20 105.93(15) . . ?
C8 C19 C20 133.91(15) . . ?
C6 C20 C15 117.38(16) . . ?
C6 C20 C19 135.95(17) . . ?
C15 C20 C19 106.58(15) . . ?
C12 C21 C8 118.38(16) . . ?
C12 C21 C22 122.72(16) . . ?
C8 C21 C22 118.90(15) . . ?
C7 C22 C21 120.44(15) . . ?
C7 C22 C17 105.63(15) . . ?
C21 C22 C17 133.89(16) . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.050
_database_code_depnum_ccdc_archive 'CCDC 993542'
