# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2013

#######################################################################
#
#                 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
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#  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_i41a
#TrackingRef 'i41a.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H14 N2'
_chemical_formula_sum            'C15 H14 N2'
_chemical_formula_weight         222.28

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           Tetragonal
_symmetry_space_group_name_H-M   'I4(1)/a '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y+1/2, z'
'-y+3/4, x+1/4, z+1/4'
'y+1/4, -x+1/4, z+1/4'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1, z+1/2'
'-y+5/4, x+3/4, z+3/4'
'y+3/4, -x+3/4, z+3/4'
'-x, -y, -z'
'x, y-1/2, -z'
'y-3/4, -x-1/4, -z-1/4'
'-y-1/4, x-1/4, -z-1/4'
'-x+1/2, -y+1/2, -z+1/2'
'x+1/2, y, -z+1/2'
'y-1/4, -x+1/4, -z+1/4'
'-y+1/4, x+1/4, -z+1/4'

_cell_length_a                   14.4293(16)
_cell_length_b                   14.4293(16)
_cell_length_c                   22.345(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     4652.3(13)
_cell_formula_units_Z            16
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2059
_cell_measurement_theta_min      1.68
_cell_measurement_theta_max      25.05

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1888
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9850
_exptl_absorpt_correction_T_max  0.9880
_exptl_absorpt_process_details   'SADABS(Sheldrick, 1996)'

_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  'Bruker APEX CCD area-detector'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13088
_diffrn_reflns_av_R_equivalents  0.0606
_diffrn_reflns_av_sigmaI/netI    0.0364
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.68
_diffrn_reflns_theta_max         25.05
_reflns_number_total             2059
_reflns_number_gt                1169
_reflns_threshold_expression     >2\s(I)

_computing_data_collection       'SMART (Bruker, 1997)'
_computing_cell_refinement       'SMART (Bruker, 1997)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97(Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL-PLUS (Sheldrick, 1990)'
_computing_publication_material  SHELXL-97

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.1859P)^2^+82.7234P] where P=(Fo^2^+2Fc^2^)/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         2059
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2632
_refine_ls_R_factor_gt           0.2096
_refine_ls_wR_factor_ref         0.5567
_refine_ls_wR_factor_gt          0.5257
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_restrained_S_all      1.104
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001

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 1.2969(9) 0.3735(8) 0.0438(6) 0.077(3) Uani 1 1 d . . .
H1 H 1.2716 0.3741 0.0821 0.092 Uiso 1 1 calc R . .
C2 C 1.3922(9) 0.3728(9) 0.0349(6) 0.084(4) Uani 1 1 d . . .
H2 H 1.4300 0.3747 0.0686 0.100 Uiso 1 1 calc R . .
C3 C 1.4343(8) 0.3695(9) -0.0196(7) 0.085(4) Uani 1 1 d . . .
H3 H 1.4985 0.3694 -0.0230 0.101 Uiso 1 1 calc R . .
C4 C 1.3773(8) 0.3661(9) -0.0708(6) 0.081(4) Uani 1 1 d . . .
H4 H 1.4030 0.3617 -0.1088 0.098 Uiso 1 1 calc R . .
C5 C 1.2836(6) 0.3696(8) -0.0633(6) 0.073(3) Uani 1 1 d . . .
H5 H 1.2465 0.3696 -0.0973 0.088 Uiso 1 1 calc R . .
C6 C 1.2402(7) 0.3731(7) -0.0075(6) 0.068(3) Uani 1 1 d . . .
C7 C 1.1379(7) 0.3732(6) 0.0006(5) 0.058(3) Uani 1 1 d . . .
C8 C 1.0208(11) 0.3798(10) 0.0646(7) 0.101(5) Uani 1 1 d . . .
H8A H 1.0056 0.3291 0.0913 0.122 Uiso 1 1 calc R . .
H8B H 1.0078 0.4365 0.0864 0.122 Uiso 1 1 calc R . .
C9 C 0.9594(9) 0.3761(6) 0.0193(5) 0.065(3) Uani 1 1 d . . .
C10 C 0.9907(7) 0.3729(6) -0.0363(5) 0.060(3) Uani 1 1 d . . .
C11 C 0.9305(9) 0.3695(9) -0.0844(6) 0.081(4) Uani 1 1 d . . .
H11 H 0.9543 0.3656 -0.1230 0.097 Uiso 1 1 calc R . .
C12 C 0.8369(7) 0.3719(8) -0.0764(6) 0.079(4) Uani 1 1 d . . .
H12 H 0.7965 0.3720 -0.1089 0.094 Uiso 1 1 calc R . .
C13 C 0.8031(9) 0.3742(8) -0.0165(7) 0.079(4) Uani 1 1 d . . .
C14 C 0.8556(10) 0.3802(9) 0.0297(7) 0.091(4) Uani 1 1 d . . .
H14 H 0.8311 0.3869 0.0680 0.110 Uiso 1 1 calc R . .
C15 C 0.6961(8) 0.3791(10) -0.0095(6) 0.091(4) Uani 1 1 d . . .
H15A H 0.6675 0.3738 -0.0482 0.136 Uiso 1 1 calc R . .
H15B H 0.6792 0.4372 0.0083 0.136 Uiso 1 1 calc R . .
H15C H 0.6754 0.3292 0.0156 0.136 Uiso 1 1 calc R . .
N1 N 1.0885(7) 0.3710(6) -0.0468(4) 0.070(3) Uani 1 1 d . . .
N2 N 1.1096(7) 0.3771(7) 0.0566(5) 0.081(3) Uani 1 1 d . . .
H2A H 1.1478 0.3779 0.0861 0.097 Uiso 1 1 calc R . .

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
C1 0.076(8) 0.071(8) 0.085(9) 0.005(6) 0.007(7) -0.012(6)
C2 0.079(9) 0.086(9) 0.086(9) -0.002(7) -0.026(7) -0.005(7)
C3 0.038(6) 0.099(10) 0.117(11) 0.023(8) 0.013(7) 0.006(6)
C4 0.055(7) 0.098(9) 0.091(9) 0.026(7) 0.025(6) -0.001(6)
C5 0.031(5) 0.089(8) 0.099(9) 0.016(7) 0.005(5) 0.006(5)
C6 0.052(6) 0.062(7) 0.089(9) 0.019(6) -0.002(6) -0.002(5)
C7 0.056(6) 0.039(5) 0.080(8) -0.002(5) 0.011(6) 0.003(4)
C8 0.119(13) 0.092(10) 0.093(11) -0.009(8) 0.022(10) 0.005(9)
C9 0.088(8) 0.038(5) 0.069(8) -0.009(5) -0.019(6) 0.011(5)
C10 0.061(6) 0.035(5) 0.083(8) 0.006(5) -0.026(6) -0.006(4)
C11 0.081(8) 0.094(9) 0.069(8) 0.002(7) -0.007(6) 0.000(7)
C12 0.046(6) 0.086(9) 0.104(10) 0.002(7) 0.005(6) -0.009(5)
C13 0.069(8) 0.052(6) 0.117(11) 0.009(7) 0.006(8) 0.000(5)
C14 0.098(11) 0.085(9) 0.091(10) -0.008(8) -0.013(8) -0.002(7)
C15 0.051(7) 0.121(11) 0.101(10) -0.002(8) 0.018(6) -0.002(7)
N1 0.069(6) 0.068(6) 0.073(6) 0.010(5) -0.016(5) -0.003(5)
N2 0.062(6) 0.102(8) 0.078(7) -0.012(6) 0.005(5) -0.006(5)

_geom_special_details            
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell s.u.'s are taken
into account individually in the estimation of s.u.'s in distances, angles
and torsion angles; correlations between s.u.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'s 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 1.390(17) . ?
C1 C6 1.407(16) . ?
C1 H1 0.9300 . ?
C2 C3 1.361(18) . ?
C2 H2 0.9300 . ?
C3 C4 1.409(17) . ?
C3 H3 0.9300 . ?
C4 C5 1.362(14) . ?
C4 H4 0.9300 . ?
C5 C6 1.397(16) . ?
C5 H5 0.9300 . ?
C6 C7 1.487(14) . ?
C7 N1 1.278(14) . ?
C7 N2 1.318(14) . ?
C8 C9 1.347(17) . ?
C8 N2 1.295(16) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.323(15) . ?
C9 C14 1.517(18) . ?
C10 C11 1.382(15) . ?
C10 N1 1.432(14) . ?
C11 C12 1.362(16) . ?
C11 H11 0.9300 . ?
C12 C13 1.425(18) . ?
C12 H12 0.9300 . ?
C13 C14 1.284(18) . ?
C13 C15 1.554(16) . ?
C14 H14 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
N2 H2A 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 117.3(12) . . ?
C2 C1 H1 121.4 . . ?
C6 C1 H1 121.4 . . ?
C3 C2 C1 124.7(12) . . ?
C3 C2 H2 117.6 . . ?
C1 C2 H2 117.6 . . ?
C2 C3 C4 117.8(11) . . ?
C2 C3 H3 121.1 . . ?
C4 C3 H3 121.1 . . ?
C5 C4 C3 118.6(12) . . ?
C5 C4 H4 120.7 . . ?
C3 C4 H4 120.7 . . ?
C4 C5 C6 123.7(12) . . ?
C4 C5 H5 118.1 . . ?
C6 C5 H5 118.1 . . ?
C5 C6 C1 117.8(10) . . ?
C5 C6 C7 123.6(10) . . ?
C1 C6 C7 118.6(11) . . ?
N1 C7 N2 128.0(10) . . ?
N1 C7 C6 116.9(10) . . ?
N2 C7 C6 115.0(11) . . ?
C9 C8 N2 123.1(13) . . ?
C9 C8 H8A 106.6 . . ?
N2 C8 H8A 106.6 . . ?
C9 C8 H8B 106.6 . . ?
N2 C8 H8B 106.6 . . ?
H8A C8 H8B 106.5 . . ?
C10 C9 C8 119.0(12) . . ?
C10 C9 C14 118.9(11) . . ?
C8 C9 C14 122.1(12) . . ?
C9 C10 C11 121.1(11) . . ?
C9 C10 N1 119.4(10) . . ?
C11 C10 N1 119.5(11) . . ?
C10 C11 C12 121.4(13) . . ?
C10 C11 H11 119.3 . . ?
C12 C11 H11 119.3 . . ?
C11 C12 C13 117.6(12) . . ?
C11 C12 H12 121.2 . . ?
C13 C12 H12 121.2 . . ?
C14 C13 C12 123.7(13) . . ?
C14 C13 C15 120.2(14) . . ?
C12 C13 C15 115.8(12) . . ?
C13 C14 C9 117.1(13) . . ?
C13 C14 H14 121.4 . . ?
C9 C14 H14 121.4 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C7 N1 C10 114.4(10) . . ?
C7 N2 C8 116.1(12) . . ?
C7 N2 H2A 122.0 . . ?
C8 N2 H2A 122.0 . . ?

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 -1.7(19) . . . . ?
C1 C2 C3 C4 0(2) . . . . ?
C2 C3 C4 C5 2.2(19) . . . . ?
C3 C4 C5 C6 -2.3(19) . . . . ?
C4 C5 C6 C1 0.3(18) . . . . ?
C4 C5 C6 C7 -177.5(10) . . . . ?
C2 C1 C6 C5 1.7(16) . . . . ?
C2 C1 C6 C7 179.6(10) . . . . ?
C5 C6 C7 N1 -0.8(16) . . . . ?
C1 C6 C7 N1 -178.6(10) . . . . ?
C5 C6 C7 N2 -179.7(11) . . . . ?
C1 C6 C7 N2 2.5(14) . . . . ?
N2 C8 C9 C10 -2(2) . . . . ?
N2 C8 C9 C14 -179.5(12) . . . . ?
C8 C9 C10 C11 -179.6(11) . . . . ?
C14 C9 C10 C11 -2.5(15) . . . . ?
C8 C9 C10 N1 1.6(15) . . . . ?
C14 C9 C10 N1 178.6(9) . . . . ?
C9 C10 C11 C12 1.7(17) . . . . ?
N1 C10 C11 C12 -179.5(10) . . . . ?
C10 C11 C12 C13 -2.5(18) . . . . ?
C11 C12 C13 C14 4.7(19) . . . . ?
C11 C12 C13 C15 178.7(11) . . . . ?
C12 C13 C14 C9 -5.5(19) . . . . ?
C15 C13 C14 C9 -179.2(10) . . . . ?
C10 C9 C14 C13 4.4(17) . . . . ?
C8 C9 C14 C13 -178.6(12) . . . . ?
N2 C7 N1 C10 -0.2(16) . . . . ?
C6 C7 N1 C10 -178.9(8) . . . . ?
C9 C10 N1 C7 -0.3(13) . . . . ?
C11 C10 N1 C7 -179.2(10) . . . . ?
N1 C7 N2 C8 -0.6(18) . . . . ?
C6 C7 N2 C8 178.2(11) . . . . ?
C9 C8 N2 C7 2(2) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.610
_refine_diff_density_min         -0.436
_refine_diff_density_rms         0.113


_database_code_depnum_ccdc_archive 'CCDC 932059'