# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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. 
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#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1811979'
_audit_update_record             
;
2017-12-16 deposited with the CCDC.	2019-09-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H16 N2'
_chemical_formula_sum            'C19 H16 N2'
_chemical_formula_weight         272.34

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.0425(5)
_cell_length_b                   12.1560(7)
_cell_length_c                   14.5478(9)
_cell_angle_alpha                90
_cell_angle_beta                 97.933(2)
_cell_angle_gamma                90
_cell_volume                     1408.65(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    2185
_cell_measurement_theta_min      3.4
_cell_measurement_theta_max      25.0

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_F_000             576.0
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_absorpt_coefficient_mu    0.076
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9780
_exptl_absorpt_correction_T_max  0.9879
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Xcalibur Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14062
_diffrn_reflns_av_unetI/netI     0.0637
_diffrn_reflns_av_R_equivalents  0.0599
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.557
_diffrn_reflns_theta_max         28.308
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3511
_reflns_number_gt                2258
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1795P)²+2.8757P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3509
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1204
_refine_ls_R_factor_gt           0.0739
_refine_ls_wR_factor_ref         0.2498
_refine_ls_wR_factor_gt          0.2061
_refine_ls_goodness_of_fit_ref   0.787
_refine_ls_restrained_S_all      0.787
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.6609(3) -0.12167(16) 0.80594(14) 0.0152(5) Uani 1 1 d . . . . .
N2 N -0.0456(3) -0.1679(2) 1.00498(18) 0.0280(6) Uani 1 1 d . . . . .
C7 C 0.2862(3) -0.0442(2) 0.91459(16) 0.0155(5) Uani 1 1 d . . . . .
H7 H 0.231387 0.017216 0.933980 0.019 Uiso 1 1 calc R U . . .
C3 C 0.3015(3) -0.2427(2) 0.89522(18) 0.0182(5) Uani 1 1 d . . . . .
H3 H 0.255896 -0.312153 0.901675 0.022 Uiso 1 1 calc R U . . .
C12 C 0.8836(3) -0.02068(19) 0.75084(16) 0.0143(5) Uani 1 1 d . . . . .
C6 C 0.4349(3) -0.03084(19) 0.87417(16) 0.0142(5) Uani 1 1 d . . . . .
C10 C 0.7279(3) -0.02375(19) 0.79558(16) 0.0144(5) Uani 1 1 d . . . . .
C4 C 0.4460(3) -0.2309(2) 0.85657(18) 0.0172(5) Uani 1 1 d . . . . .
H4 H 0.499176 -0.293115 0.837560 0.021 Uiso 1 1 calc R U . . .
C9 C 0.6536(3) 0.07507(19) 0.82275(17) 0.0149(5) Uani 1 1 d . . . . .
H9 H 0.704777 0.142102 0.813852 0.018 Uiso 1 1 calc R U . . .
C17 C 0.9732(3) 0.0762(2) 0.74209(17) 0.0170(5) Uani 1 1 d . . . . .
H17 H 0.939257 0.140835 0.768143 0.020 Uiso 1 1 calc R U . . .
C14 C 1.0811(3) -0.1154(2) 0.66731(17) 0.0167(5) Uani 1 1 d . . . . .
H14 H 1.117226 -0.180494 0.642929 0.020 Uiso 1 1 calc R U . . .
C11 C 0.4266(3) 0.1770(2) 0.88858(18) 0.0181(5) Uani 1 1 d . . . . .
H11A H 0.326612 0.159172 0.914601 0.027 Uiso 1 1 calc R U . . .
H11B H 0.502888 0.216121 0.933709 0.027 Uiso 1 1 calc R U . . .
H11C H 0.398101 0.222331 0.834646 0.027 Uiso 1 1 calc R U . . .
C16 C 1.1122(3) 0.07751(19) 0.69511(18) 0.0174(5) Uani 1 1 d . . . . .
H16 H 1.168515 0.143356 0.689046 0.021 Uiso 1 1 calc R U . . .
C8 C 0.5081(3) 0.0734(2) 0.86175(16) 0.0153(5) Uani 1 1 d . . . . .
C1 C 0.2220(3) -0.1475(2) 0.92541(17) 0.0166(5) Uani 1 1 d . . . . .
C5 C 0.5164(3) -0.1261(2) 0.84482(17) 0.0147(5) Uani 1 1 d . . . . .
C15 C 1.1685(3) -0.0185(2) 0.65686(17) 0.0156(5) Uani 1 1 d . . . . .
C13 C 0.9414(3) -0.1170(2) 0.71322(17) 0.0168(5) Uani 1 1 d . . . . .
H13 H 0.885186 -0.182926 0.719127 0.020 Uiso 1 1 calc R U . . .
C19 C 1.2704(3) 0.0462(2) 0.51037(19) 0.0252(6) Uani 1 1 d . . . . .
H19A H 1.365586 0.046345 0.477195 0.038 Uiso 1 1 calc R U . . .
H19B H 1.177513 0.010571 0.473529 0.038 Uiso 1 1 calc R U . . .
H19C H 1.240222 0.120540 0.522919 0.038 Uiso 1 1 calc R U . . .
C2 C 0.0717(3) -0.1593(2) 0.96896(18) 0.0198(6) Uani 1 1 d . . . . .
C18 C 1.3145(3) -0.0158(2) 0.60173(18) 0.0170(5) Uani 1 1 d . . . . .
H18A H 1.346825 -0.090462 0.588889 0.020 Uiso 1 1 calc R U . . .
H18B H 1.409587 0.019600 0.638321 0.020 Uiso 1 1 calc R U . . .


_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 C10 1.324(3) . ?
N1 C5 1.362(3) . ?
N2 C2 1.145(3) . ?
C7 C1 1.376(3) . ?
C7 C6 1.413(3) . ?
C7 H7 0.9300 . ?
C3 C4 1.367(3) . ?
C3 C1 1.421(3) . ?
C3 H3 0.9300 . ?
C12 C13 1.398(3) . ?
C12 C17 1.395(3) . ?
C12 C10 1.489(3) . ?
C6 C8 1.420(3) . ?
C6 C5 1.425(3) . ?
C10 C9 1.422(3) . ?
C4 C5 1.413(3) . ?
C4 H4 0.9300 . ?
C9 C8 1.369(3) . ?
C9 H9 0.9300 . ?
C17 C16 1.388(3) . ?
C17 H17 0.9300 . ?
C14 C13 1.384(3) . ?
C14 C15 1.391(3) . ?
C14 H14 0.9300 . ?
C11 C8 1.497(3) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C16 C15 1.395(3) . ?
C16 H16 0.9300 . ?
C1 C2 1.448(3) . ?
C15 C18 1.511(3) . ?
C13 H13 0.9300 . ?
C19 C18 1.526(4) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?

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
C10 N1 C5 117.9(2) . . ?
C1 C7 C6 120.3(2) . . ?
C1 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C4 C3 C1 119.0(2) . . ?
C4 C3 H3 120.5 . . ?
C1 C3 H3 120.5 . . ?
C13 C12 C17 117.8(2) . . ?
C13 C12 C10 119.6(2) . . ?
C17 C12 C10 122.5(2) . . ?
C7 C6 C8 123.1(2) . . ?
C7 C6 C5 118.8(2) . . ?
C8 C6 C5 118.1(2) . . ?
N1 C10 C9 122.3(2) . . ?
N1 C10 C12 116.9(2) . . ?
C9 C10 C12 120.8(2) . . ?
C3 C4 C5 121.5(2) . . ?
C3 C4 H4 119.2 . . ?
C5 C4 H4 119.2 . . ?
C8 C9 C10 121.3(2) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 H9 119.4 . . ?
C16 C17 C12 121.1(2) . . ?
C16 C17 H17 119.5 . . ?
C12 C17 H17 119.5 . . ?
C13 C14 C15 121.4(2) . . ?
C13 C14 H14 119.3 . . ?
C15 C14 H14 119.3 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C17 C16 C15 120.9(2) . . ?
C17 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
C9 C8 C6 117.3(2) . . ?
C9 C8 C11 121.7(2) . . ?
C6 C8 C11 120.9(2) . . ?
C7 C1 C3 121.1(2) . . ?
C7 C1 C2 119.3(2) . . ?
C3 C1 C2 119.6(2) . . ?
N1 C5 C4 117.7(2) . . ?
N1 C5 C6 123.1(2) . . ?
C4 C5 C6 119.1(2) . . ?
C14 C15 C16 117.9(2) . . ?
C14 C15 C18 121.2(2) . . ?
C16 C15 C18 120.8(2) . . ?
C14 C13 C12 120.8(2) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N2 C2 C1 178.7(3) . . ?
C15 C18 C19 111.7(2) . . ?
C15 C18 H18A 109.3 . . ?
C19 C18 H18A 109.3 . . ?
C15 C18 H18B 109.3 . . ?
C19 C18 H18B 109.3 . . ?
H18A C18 H18B 107.9 . . ?

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
C1 C7 C6 C8 -179.5(2) . . . . ?
C1 C7 C6 C5 0.1(4) . . . . ?
C5 N1 C10 C9 -0.5(4) . . . . ?
C5 N1 C10 C12 -178.6(2) . . . . ?
C13 C12 C10 N1 6.9(3) . . . . ?
C17 C12 C10 N1 -175.2(2) . . . . ?
C13 C12 C10 C9 -171.2(2) . . . . ?
C17 C12 C10 C9 6.8(4) . . . . ?
C1 C3 C4 C5 -0.9(4) . . . . ?
N1 C10 C9 C8 0.3(4) . . . . ?
C12 C10 C9 C8 178.3(2) . . . . ?
C13 C12 C17 C16 1.9(4) . . . . ?
C10 C12 C17 C16 -176.1(2) . . . . ?
C12 C17 C16 C15 -1.3(4) . . . . ?
C10 C9 C8 C6 0.2(4) . . . . ?
C10 C9 C8 C11 -178.6(2) . . . . ?
C7 C6 C8 C9 179.2(2) . . . . ?
C5 C6 C8 C9 -0.4(3) . . . . ?
C7 C6 C8 C11 -2.1(4) . . . . ?
C5 C6 C8 C11 178.3(2) . . . . ?
C6 C7 C1 C3 -0.9(4) . . . . ?
C6 C7 C1 C2 178.6(2) . . . . ?
C4 C3 C1 C7 1.3(4) . . . . ?
C4 C3 C1 C2 -178.2(2) . . . . ?
C10 N1 C5 C4 -179.4(2) . . . . ?
C10 N1 C5 C6 0.3(4) . . . . ?
C3 C4 C5 N1 179.8(2) . . . . ?
C3 C4 C5 C6 0.1(4) . . . . ?
C7 C6 C5 N1 -179.4(2) . . . . ?
C8 C6 C5 N1 0.2(4) . . . . ?
C7 C6 C5 C4 0.3(4) . . . . ?
C8 C6 C5 C4 179.9(2) . . . . ?
C13 C14 C15 C16 0.7(4) . . . . ?
C13 C14 C15 C18 -176.2(2) . . . . ?
C17 C16 C15 C14 0.0(4) . . . . ?
C17 C16 C15 C18 177.0(2) . . . . ?
C15 C14 C13 C12 -0.1(4) . . . . ?
C17 C12 C13 C14 -1.2(4) . . . . ?
C10 C12 C13 C14 176.9(2) . . . . ?
C14 C15 C18 C19 109.2(3) . . . . ?
C16 C15 C18 C19 -67.7(3) . . . . ?

_refine_diff_density_max         0.662
_refine_diff_density_min         -0.623
_refine_diff_density_rms         0.082

