# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_son-387-5
_database_code_depnum_ccdc_archive 'CCDC 1486060'
_audit_update_record             
;
2016-06-16 deposited with the CCDC.
2016-08-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H14 N2'
_chemical_formula_sum            'C19 H14 N2'
_chemical_formula_weight         270.32

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_space_group_name_Hall  '-P 2ybc'

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                   13.739(5)
_cell_length_b                   5.908(5)
_cell_length_c                   17.319(5)
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 91.208(5)
_cell_angle_gamma                90.000(5)
_cell_volume                     1405.5(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1602
_cell_measurement_theta_min      3.70
_cell_measurement_theta_max      25.00

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.17
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             568
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9850
_exptl_absorpt_correction_T_max  0.9872
_exptl_absorpt_process_details   crysalispro

_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  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15507
_diffrn_reflns_av_R_equivalents  0.0390
_diffrn_reflns_av_sigmaI/netI    0.0330
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.64
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2465
_reflns_number_gt                1602
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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 > 2σ(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)+(0.0641P)²+0.0476P] 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         2465
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0823
_refine_ls_R_factor_gt           0.0514
_refine_ls_wR_factor_ref         0.1365
_refine_ls_wR_factor_gt          0.1235
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.001
_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 0.40506(13) 0.1655(3) 0.44700(9) 0.0418(5) Uani 1 1 d . . .
C2 C 0.35923(14) 0.3199(3) 0.49735(10) 0.0492(5) Uani 1 1 d . . .
H2 H 0.3899 0.4555 0.5102 0.059 Uiso 1 1 calc R . .
C3 C 0.27162(15) 0.2719(4) 0.52673(11) 0.0586(6) Uani 1 1 d . . .
H3 H 0.2426 0.3753 0.5595 0.070 Uiso 1 1 calc R . .
C4 C 0.22292(15) 0.0666(4) 0.50853(11) 0.0625(6) Uani 1 1 d . . .
H4 H 0.1622 0.0371 0.5290 0.075 Uiso 1 1 calc R . .
C5 C 0.26440(14) -0.0864(3) 0.46147(11) 0.0544(5) Uani 1 1 d . . .
H5 H 0.2319 -0.2206 0.4499 0.065 Uiso 1 1 calc R . .
C6 C 0.35689(13) -0.0445(3) 0.42960(9) 0.0427(5) Uani 1 1 d . . .
C7 C 0.40452(14) -0.1980(3) 0.38311(9) 0.0436(5) Uani 1 1 d . . .
H7 H 0.3759 -0.3367 0.3713 0.052 Uiso 1 1 calc R . .
C8 C 0.49430(13) -0.1442(3) 0.35455(9) 0.0391(5) Uani 1 1 d . . .
C9 C 0.54940(14) -0.2920(3) 0.30785(9) 0.0445(5) Uani 1 1 d . . .
H9 H 0.5240 -0.4354 0.2982 0.053 Uiso 1 1 calc R . .
C10 C 0.67079(13) -0.0284(3) 0.29140(9) 0.0420(5) Uani 1 1 d . . .
C11 C 0.62542(13) 0.1225(3) 0.33837(10) 0.0427(5) Uani 1 1 d . . .
H11 H 0.6544 0.2621 0.3483 0.051 Uiso 1 1 calc R . .
C12 C 0.53552(13) 0.0710(3) 0.37219(9) 0.0391(5) Uani 1 1 d . . .
C13 C 0.76147(13) 0.0219(3) 0.25056(10) 0.0456(5) Uani 1 1 d . . .
C14 C 0.79904(15) -0.1294(4) 0.19820(12) 0.0618(6) Uani 1 1 d . . .
H14 H 0.7682 -0.2680 0.1904 0.074 Uiso 1 1 calc R . .
C15 C 0.88104(16) -0.0796(4) 0.15731(13) 0.0726(7) Uani 1 1 d . . .
H15 H 0.9042 -0.1852 0.1224 0.087 Uiso 1 1 calc R . .
C16 C 0.92971(15) 0.1226(4) 0.16667(12) 0.0656(6) Uani 1 1 d . . .
C17 C 0.89248(16) 0.2734(4) 0.21825(14) 0.0764(7) Uani 1 1 d . . .
H17 H 0.9234 0.4119 0.2257 0.092 Uiso 1 1 calc R . .
C18 C 0.81071(16) 0.2254(4) 0.25922(13) 0.0694(7) Uani 1 1 d . . .
H18 H 0.7876 0.3323 0.2938 0.083 Uiso 1 1 calc R . .
C19 C 1.01811(18) 0.1793(5) 0.11998(15) 0.0995(9) Uani 1 1 d . . .
H19A H 1.0415 0.3270 0.1342 0.149 Uiso 1 1 calc R . .
H19B H 1.0008 0.1776 0.0660 0.149 Uiso 1 1 calc R . .
H19C H 1.0682 0.0693 0.1301 0.149 Uiso 1 1 calc R . .
N1 N 0.49207(11) 0.2219(2) 0.41828(8) 0.0433(4) Uani 1 1 d . . .
N2 N 0.63258(11) -0.2430(3) 0.27743(8) 0.0472(4) Uani 1 1 d . . .


_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 N1 1.346(2) . ?
C1 C2 1.418(2) . ?
C1 C6 1.435(3) . ?
C2 C3 1.347(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.418(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.351(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.418(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.386(2) . ?
C7 C8 1.376(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.419(2) . ?
C8 C12 1.423(3) . ?
C9 N2 1.301(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.366(2) . ?
C10 N2 1.392(2) . ?
C10 C13 1.476(2) . ?
C11 C12 1.411(2) . ?
C11 H11 0.9300 . ?
C12 N1 1.345(2) . ?
C13 C14 1.381(2) . ?
C13 C18 1.386(3) . ?
C14 C15 1.375(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.377(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.369(3) . ?
C16 C19 1.511(3) . ?
C17 C18 1.371(3) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?

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
N1 C1 C2 118.49(17) . . ?
N1 C1 C6 123.06(17) . . ?
C2 C1 C6 118.45(18) . . ?
C3 C2 C1 120.58(19) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C2 C3 C4 121.16(19) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C5 C4 C3 120.2(2) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 120.73(19) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C7 C6 C5 123.37(18) . . ?
C7 C6 C1 117.79(17) . . ?
C5 C6 C1 118.83(17) . . ?
C8 C7 C6 119.73(17) . . ?
C8 C7 H7 120.1 . . ?
C6 C7 H7 120.1 . . ?
C7 C8 C9 123.78(17) . . ?
C7 C8 C12 119.01(16) . . ?
C9 C8 C12 117.21(17) . . ?
N2 C9 C8 125.28(18) . . ?
N2 C9 H9 117.4 . . ?
C8 C9 H9 117.4 . . ?
C11 C10 N2 121.52(17) . . ?
C11 C10 C13 123.66(17) . . ?
N2 C10 C13 114.80(16) . . ?
C10 C11 C12 121.38(17) . . ?
C10 C11 H11 119.3 . . ?
C12 C11 H11 119.3 . . ?
N1 C12 C11 120.45(16) . . ?
N1 C12 C8 122.71(17) . . ?
C11 C12 C8 116.84(16) . . ?
C14 C13 C18 116.38(19) . . ?
C14 C13 C10 121.00(18) . . ?
C18 C13 C10 122.54(18) . . ?
C15 C14 C13 121.4(2) . . ?
C15 C14 H14 119.3 . . ?
C13 C14 H14 119.3 . . ?
C14 C15 C16 121.8(2) . . ?
C14 C15 H15 119.1 . . ?
C16 C15 H15 119.1 . . ?
C17 C16 C15 117.0(2) . . ?
C17 C16 C19 121.4(2) . . ?
C15 C16 C19 121.6(2) . . ?
C16 C17 C18 121.7(2) . . ?
C16 C17 H17 119.2 . . ?
C18 C17 H17 119.2 . . ?
C17 C18 C13 121.8(2) . . ?
C17 C18 H18 119.1 . . ?
C13 C18 H18 119.1 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C12 N1 C1 117.64(15) . . ?
C9 N2 C10 117.63(16) . . ?

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
N1 C1 C2 C3 179.20(16) . . . . ?
C6 C1 C2 C3 -1.4(3) . . . . ?
C1 C2 C3 C4 0.2(3) . . . . ?
C2 C3 C4 C5 0.5(3) . . . . ?
C3 C4 C5 C6 0.0(3) . . . . ?
C4 C5 C6 C7 177.77(17) . . . . ?
C4 C5 C6 C1 -1.2(3) . . . . ?
N1 C1 C6 C7 2.3(2) . . . . ?
C2 C1 C6 C7 -177.17(14) . . . . ?
N1 C1 C6 C5 -178.74(15) . . . . ?
C2 C1 C6 C5 1.8(2) . . . . ?
C5 C6 C7 C8 -179.91(16) . . . . ?
C1 C6 C7 C8 -1.0(2) . . . . ?
C6 C7 C8 C9 178.69(15) . . . . ?
C6 C7 C8 C12 -1.3(2) . . . . ?
C7 C8 C9 N2 177.10(16) . . . . ?
C12 C8 C9 N2 -2.9(3) . . . . ?
N2 C10 C11 C12 -2.8(3) . . . . ?
C13 C10 C11 C12 175.91(15) . . . . ?
C10 C11 C12 N1 179.98(15) . . . . ?
C10 C11 C12 C8 -0.5(2) . . . . ?
C7 C8 C12 N1 2.7(2) . . . . ?
C9 C8 C12 N1 -177.36(15) . . . . ?
C7 C8 C12 C11 -176.90(15) . . . . ?
C9 C8 C12 C11 3.1(2) . . . . ?
C11 C10 C13 C14 -173.85(17) . . . . ?
N2 C10 C13 C14 4.9(2) . . . . ?
C11 C10 C13 C18 2.8(3) . . . . ?
N2 C10 C13 C18 -178.42(17) . . . . ?
C18 C13 C14 C15 0.2(3) . . . . ?
C10 C13 C14 C15 177.02(17) . . . . ?
C13 C14 C15 C16 0.2(3) . . . . ?
C14 C15 C16 C17 -0.5(3) . . . . ?
C14 C15 C16 C19 -178.3(2) . . . . ?
C15 C16 C17 C18 0.4(4) . . . . ?
C19 C16 C17 C18 178.2(2) . . . . ?
C16 C17 C18 C13 0.0(4) . . . . ?
C14 C13 C18 C17 -0.3(3) . . . . ?
C10 C13 C18 C17 -177.05(19) . . . . ?
C11 C12 N1 C1 178.11(15) . . . . ?
C8 C12 N1 C1 -1.4(2) . . . . ?
C2 C1 N1 C12 178.38(14) . . . . ?
C6 C1 N1 C12 -1.0(2) . . . . ?
C8 C9 N2 C10 -0.3(3) . . . . ?
C11 C10 N2 C9 3.1(2) . . . . ?
C13 C10 N2 C9 -175.66(15) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.149
_refine_diff_density_rms         0.034
