# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1400529'
_audit_update_record             
;
2015-05-12 deposited with the CCDC.
2015-06-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97

_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H16 N2'
_chemical_formula_weight         308.37

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

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                   11.9993(9)
_cell_length_b                   4.2453(3)
_cell_length_c                   29.803(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.261(4)
_cell_angle_gamma                90.00
_cell_volume                     1493.90(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(1)
_exptl_crystal_description       plate
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.04

_exptl_crystal_density_diffrn    1.371
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             648
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2007)'
_exptl_absorpt_correction_T_min  0.4717
_exptl_absorpt_correction_T_max  0.7452
_diffrn_ambient_temperature      100(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'CCD Area Detector'
_diffrn_measurement_device_type  'Bruker APEXII'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_reflns_number            32407
_diffrn_reflns_av_R_equivalents  0.0637
_diffrn_reflns_av_sigmaI/netI    0.0286
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         1.39
_diffrn_reflns_theta_max         25.38
_reflns_number_total             2740
_reflns_number_gt                2217
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0928P)²+0.5028P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2740
_refine_ls_number_parameters     219
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0664
_refine_ls_R_factor_gt           0.0541
_refine_ls_wR_factor_ref         0.1579
_refine_ls_wR_factor_gt          0.1464
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_restrained_S_all      1.104
_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 0.64393(12) 0.5981(4) 0.15620(5) 0.0262(4) Uani 1 1 d . . .
N2 N 0.69448(12) 0.7769(4) 0.19255(5) 0.0265(4) Uani 1 1 d . . .
C3 C 0.79832(14) 0.8685(4) 0.19394(6) 0.0250(4) Uani 1 1 d . . .
C4 C 0.86460(14) 0.7887(4) 0.15915(6) 0.0246(4) Uani 1 1 d . . .
C5 C 0.97499(15) 0.8933(4) 0.16039(6) 0.0272(4) Uani 1 1 d . . .
H5 H 1.0095 1.0227 0.1840 0.036 Uiso 1 1 calc R . .
C6 C 1.03323(15) 0.8039(5) 0.12630(6) 0.0287(4) Uani 1 1 d . . .
H6 H 1.1068 0.8757 0.1272 0.038 Uiso 1 1 calc R . .
C7 C 0.98443(14) 0.6109(5) 0.09114(6) 0.0273(4) Uani 1 1 d . . .
H7 H 1.0258 0.5535 0.0688 0.036 Uiso 1 1 calc R . .
C8 C 0.87253(14) 0.4984(4) 0.08837(6) 0.0239(4) Uani 1 1 d . . .
C9 C 0.81821(14) 0.2916(4) 0.05224(6) 0.0237(4) Uani 1 1 d . . .
C10 C 0.86942(15) 0.1938(5) 0.01571(6) 0.0275(4) Uani 1 1 d . . .
H10 H 0.9421 0.2637 0.0142 0.037 Uiso 1 1 calc R . .
C11 C 0.81493(15) -0.0022(5) -0.01789(6) 0.0294(5) Uani 1 1 d . . .
H11 H 0.8502 -0.0603 -0.0420 0.039 Uiso 1 1 calc R . .
C12 C 0.70608(15) -0.1145(5) -0.01582(6) 0.0300(5) Uani 1 1 d . . .
H12 H 0.6693 -0.2488 -0.0383 0.040 Uiso 1 1 calc R . .
C13 C 0.65433(15) -0.0255(4) 0.01956(6) 0.0274(4) Uani 1 1 d . . .
H13 H 0.5827 -0.1040 0.0211 0.036 Uiso 1 1 calc R . .
C14 C 0.70695(14) 0.1827(4) 0.05384(6) 0.0243(4) Uani 1 1 d . . .
C15 C 0.64928(14) 0.2819(4) 0.08886(6) 0.0247(4) Uani 1 1 d . . .
H15 H 0.5767 0.2068 0.0893 0.033 Uiso 1 1 calc R . .
C16 C 0.69851(14) 0.4866(4) 0.12204(5) 0.0227(4) Uani 1 1 d . . .
C17 C 0.81299(14) 0.5917(4) 0.12295(6) 0.0231(4) Uani 1 1 d . . .
C18 C 0.52757(14) 0.5255(5) 0.15756(6) 0.0248(4) Uani 1 1 d . . .
C19 C 0.44281(15) 0.6202(5) 0.12186(6) 0.0276(4) Uani 1 1 d . . .
H19 H 0.4613 0.7242 0.0967 0.037 Uiso 1 1 calc R . .
C20 C 0.33085(14) 0.5578(5) 0.12421(6) 0.0288(5) Uani 1 1 d . . .
H20 H 0.2739 0.6192 0.1004 0.038 Uiso 1 1 calc R . .
C21 C 0.30300(15) 0.4052(5) 0.16161(6) 0.0299(5) Uani 1 1 d . . .
H21 H 0.2276 0.3647 0.1630 0.040 Uiso 1 1 calc R . .
C22 C 0.38806(15) 0.3123(5) 0.19707(6) 0.0307(5) Uani 1 1 d . . .
H22 H 0.3693 0.2118 0.2224 0.041 Uiso 1 1 calc R . .
C23 C 0.50051(15) 0.3687(5) 0.19482(6) 0.0290(5) Uani 1 1 d . . .
H23 H 0.5575 0.3016 0.2182 0.039 Uiso 1 1 calc R . .
C24 C 0.84795(15) 1.0652(5) 0.23445(6) 0.0304(5) Uani 1 1 d . . .
H24A H 0.7912 1.1041 0.2528 0.046 Uiso 1 1 calc R . .
H24B H 0.8738 1.2621 0.2242 0.046 Uiso 1 1 calc R . .
H24C H 0.9106 0.9553 0.2523 0.046 Uiso 1 1 calc R . .


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 N2 1.372(2) . ?
N1 C16 1.388(2) . ?
N1 C18 1.437(2) . ?
N2 C3 1.299(2) . ?
C3 C4 1.455(2) . ?
C3 C24 1.501(2) . ?
C4 C5 1.391(2) . ?
C4 C17 1.418(3) . ?
C5 C6 1.385(3) . ?
C6 C7 1.376(3) . ?
C7 C8 1.414(2) . ?
C8 C17 1.411(2) . ?
C8 C9 1.451(3) . ?
C9 C10 1.405(2) . ?
C9 C14 1.421(2) . ?
C10 C11 1.374(3) . ?
C11 C12 1.402(3) . ?
C12 C13 1.369(3) . ?
C13 C14 1.412(2) . ?
C14 C15 1.415(2) . ?
C15 C16 1.369(3) . ?
C16 C17 1.440(2) . ?
C18 C23 1.382(3) . ?
C18 C19 1.394(2) . ?
C19 C20 1.383(2) . ?
C20 C21 1.381(3) . ?
C21 C22 1.389(3) . ?
C22 C23 1.384(3) . ?

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
N2 N1 C16 124.58(14) . . ?
N2 N1 C18 113.03(13) . . ?
C16 N1 C18 122.36(14) . . ?
C3 N2 N1 118.52(15) . . ?
N2 C3 C4 123.41(16) . . ?
N2 C3 C24 115.67(15) . . ?
C4 C3 C24 120.92(15) . . ?
C5 C4 C17 119.57(16) . . ?
C5 C4 C3 123.06(16) . . ?
C17 C4 C3 117.37(16) . . ?
C6 C5 C4 119.69(17) . . ?
C7 C6 C5 121.34(17) . . ?
C6 C7 C8 121.09(17) . . ?
C17 C8 C7 117.50(16) . . ?
C17 C8 C9 119.52(16) . . ?
C7 C8 C9 122.98(16) . . ?
C10 C9 C14 118.23(16) . . ?
C10 C9 C8 123.58(16) . . ?
C14 C9 C8 118.19(16) . . ?
C11 C10 C9 121.75(17) . . ?
C10 C11 C12 120.00(17) . . ?
C13 C12 C11 119.60(17) . . ?
C12 C13 C14 121.64(17) . . ?
C13 C14 C15 120.37(16) . . ?
C13 C14 C9 118.74(16) . . ?
C15 C14 C9 120.89(16) . . ?
C16 C15 C14 121.13(16) . . ?
C15 C16 N1 123.16(16) . . ?
C15 C16 C17 119.84(16) . . ?
N1 C16 C17 116.99(15) . . ?
C8 C17 C4 120.81(16) . . ?
C8 C17 C16 120.31(16) . . ?
C4 C17 C16 118.88(16) . . ?
C23 C18 C19 120.56(16) . . ?
C23 C18 N1 119.64(15) . . ?
C19 C18 N1 119.79(16) . . ?
C20 C19 C18 119.29(17) . . ?
C21 C20 C19 120.51(16) . . ?
C20 C21 C22 119.78(16) . . ?
C23 C22 C21 120.31(17) . . ?
C18 C23 C22 119.54(16) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.38
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.308
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.061
