# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 1584272'
_audit_update_record             
;
2017-11-07 deposited with the CCDC.
2018-05-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H13 N'
_chemical_formula_weight         243.29

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           Orthorhombic
_symmetry_space_group_name_H-M   'Fdd2 '

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

_cell_length_a                   12.7887(15)
_cell_length_b                   38.1950(19)
_cell_length_c                   10.8230(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     5286.6(10)
_cell_formula_units_Z            16
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    599
_cell_measurement_theta_min      2.52
_cell_measurement_theta_max      16.64

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.223
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2048
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9769
_exptl_absorpt_correction_T_max  0.9852
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_number            6523
_diffrn_reflns_av_R_equivalents  0.0936
_diffrn_reflns_av_sigmaI/netI    0.0807
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -43
_diffrn_reflns_limit_k_max       45
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         2.52
_diffrn_reflns_theta_max         24.99
_reflns_number_total             1834
_reflns_number_gt                992
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0006P)²+0.1000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.00095(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1834
_refine_ls_number_parameters     173
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1072
_refine_ls_R_factor_gt           0.0427
_refine_ls_wR_factor_ref         0.0633
_refine_ls_wR_factor_gt          0.0544
_refine_ls_goodness_of_fit_ref   0.982
_refine_ls_restrained_S_all      0.982
_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 0.42860(17) 0.05028(6) 0.8325(3) 0.0709(7) Uani 1 1 d . . .
C1 C 0.4930(3) 0.05944(8) 0.7335(4) 0.0770(9) Uani 1 1 d . . .
C2 C 0.4876(3) 0.04876(8) 0.6123(4) 0.0975(11) Uani 1 1 d . . .
H2A H 0.4357 0.0334 0.5861 0.117 Uiso 1 1 calc R . .
C3 C 0.5609(4) 0.06142(11) 0.5313(4) 0.1182(15) Uani 1 1 d . . .
H3A H 0.5583 0.0549 0.4486 0.142 Uiso 1 1 calc R . .
C4 C 0.6385(4) 0.08379(12) 0.5714(6) 0.1278(18) Uani 1 1 d . . .
H4A H 0.6871 0.0919 0.5143 0.153 Uiso 1 1 calc R . .
C5 C 0.6470(3) 0.09461(10) 0.6930(5) 0.1133(15) Uani 1 1 d . . .
H5A H 0.6997 0.1097 0.7187 0.136 Uiso 1 1 calc R . .
C6 C 0.5722(3) 0.08167(8) 0.7751(4) 0.0824(10) Uani 1 1 d . . .
C7 C 0.5546(2) 0.08629(8) 0.9044(4) 0.0782(10) Uani 1 1 d . . .
C8 C 0.6037(3) 0.10545(9) 0.9972(5) 0.1047(13) Uani 1 1 d . . .
H8A H 0.6634 0.1184 0.9792 0.126 Uiso 1 1 calc R . .
C9 C 0.5650(3) 0.10529(8) 1.1137(5) 0.1108(15) Uani 1 1 d . . .
H9A H 0.5987 0.1181 1.1749 0.133 Uiso 1 1 calc R . .
C10 C 0.4751(3) 0.08619(8) 1.1436(4) 0.0986(12) Uani 1 1 d . . .
H10A H 0.4493 0.0866 1.2239 0.118 Uiso 1 1 calc R . .
C11 C 0.4249(2) 0.06684(7) 1.0546(3) 0.0768(9) Uani 1 1 d . . .
H11A H 0.3649 0.0541 1.0733 0.092 Uiso 1 1 calc R . .
C12 C 0.4656(2) 0.06684(7) 0.9376(4) 0.0705(9) Uani 1 1 d . . .
C13 C 0.3371(2) 0.02992(8) 0.8240(3) 0.0666(8) Uani 1 1 d . . .
C14 C 0.2570(2) 0.04014(8) 0.7477(3) 0.0823(10) Uani 1 1 d . . .
H14A H 0.2630 0.0605 0.7011 0.099 Uiso 1 1 calc R . .
C15 C 0.1684(3) 0.02032(10) 0.7406(3) 0.0926(10) Uani 1 1 d . . .
H15A H 0.1141 0.0272 0.6889 0.111 Uiso 1 1 calc R . .
C16 C 0.1593(3) -0.00960(10) 0.8091(4) 0.0935(11) Uani 1 1 d . . .
H16A H 0.0986 -0.0230 0.8042 0.112 Uiso 1 1 calc R . .
C17 C 0.2386(3) -0.01989(8) 0.8846(4) 0.0897(10) Uani 1 1 d . . .
H17A H 0.2319 -0.0401 0.9320 0.108 Uiso 1 1 calc R . .
C18 C 0.3286(2) -0.00033(7) 0.8907(3) 0.0750(9) Uani 1 1 d . . .
H18A H 0.3838 -0.0077 0.9402 0.090 Uiso 1 1 calc R . .


_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 C12 1.384(3) . ?
N1 C1 1.397(4) . ?
N1 C13 1.408(3) . ?
C1 C2 1.375(4) . ?
C1 C6 1.396(4) . ?
C2 C3 1.372(4) . ?
C2 H2A 0.9300 . ?
C3 C4 1.379(5) . ?
C3 H3A 0.9300 . ?
C4 C5 1.384(6) . ?
C4 H4A 0.9300 . ?
C5 C6 1.396(5) . ?
C5 H5A 0.9300 . ?
C6 C7 1.429(4) . ?
C7 C8 1.393(5) . ?
C7 C12 1.406(4) . ?
C8 C9 1.355(5) . ?
C8 H8A 0.9300 . ?
C9 C10 1.399(4) . ?
C9 H9A 0.9300 . ?
C10 C11 1.374(4) . ?
C10 H10A 0.9300 . ?
C11 C12 1.369(4) . ?
C11 H11A 0.9300 . ?
C13 C18 1.367(3) . ?
C13 C14 1.372(4) . ?
C14 C15 1.364(4) . ?
C14 H14A 0.9300 . ?
C15 C16 1.368(4) . ?
C15 H15A 0.9300 . ?
C16 C17 1.360(4) . ?
C16 H16A 0.9300 . ?
C17 C18 1.374(3) . ?
C17 H17A 0.9300 . ?
C18 H18A 0.9300 . ?

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
C12 N1 C1 108.3(3) . . ?
C12 N1 C13 126.2(3) . . ?
C1 N1 C13 125.3(3) . . ?
C2 C1 C6 121.7(4) . . ?
C2 C1 N1 128.9(3) . . ?
C6 C1 N1 109.4(4) . . ?
C3 C2 C1 118.1(4) . . ?
C3 C2 H2A 121.0 . . ?
C1 C2 H2A 121.0 . . ?
C2 C3 C4 120.6(4) . . ?
C2 C3 H3A 119.7 . . ?
C4 C3 H3A 119.7 . . ?
C3 C4 C5 122.7(5) . . ?
C3 C4 H4A 118.6 . . ?
C5 C4 H4A 118.6 . . ?
C4 C5 C6 116.5(4) . . ?
C4 C5 H5A 121.8 . . ?
C6 C5 H5A 121.8 . . ?
C1 C6 C5 120.5(4) . . ?
C1 C6 C7 106.1(4) . . ?
C5 C6 C7 133.4(4) . . ?
C8 C7 C12 117.4(4) . . ?
C8 C7 C6 134.4(4) . . ?
C12 C7 C6 108.2(4) . . ?
C9 C8 C7 120.2(4) . . ?
C9 C8 H8A 119.9 . . ?
C7 C8 H8A 119.9 . . ?
C8 C9 C10 121.2(4) . . ?
C8 C9 H9A 119.4 . . ?
C10 C9 H9A 119.4 . . ?
C11 C10 C9 120.2(4) . . ?
C11 C10 H10A 119.9 . . ?
C9 C10 H10A 119.9 . . ?
C12 C11 C10 118.1(3) . . ?
C12 C11 H11A 121.0 . . ?
C10 C11 H11A 121.0 . . ?
C11 C12 N1 129.0(3) . . ?
C11 C12 C7 122.9(4) . . ?
N1 C12 C7 108.0(3) . . ?
C18 C13 C14 119.9(3) . . ?
C18 C13 N1 119.9(3) . . ?
C14 C13 N1 120.2(3) . . ?
C15 C14 C13 119.7(3) . . ?
C15 C14 H14A 120.1 . . ?
C13 C14 H14A 120.1 . . ?
C14 C15 C16 120.3(3) . . ?
C14 C15 H15A 119.9 . . ?
C16 C15 H15A 119.9 . . ?
C17 C16 C15 120.2(3) . . ?
C17 C16 H16A 119.9 . . ?
C15 C16 H16A 119.9 . . ?
C16 C17 C18 119.7(3) . . ?
C16 C17 H17A 120.1 . . ?
C18 C17 H17A 120.1 . . ?
C13 C18 C17 120.1(3) . . ?
C13 C18 H18A 120.0 . . ?
C17 C18 H18A 120.0 . . ?

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
C12 N1 C1 C2 178.6(3) . . . . ?
C13 N1 C1 C2 -6.0(5) . . . . ?
C12 N1 C1 C6 0.6(3) . . . . ?
C13 N1 C1 C6 175.9(2) . . . . ?
C6 C1 C2 C3 -1.9(5) . . . . ?
N1 C1 C2 C3 -179.7(3) . . . . ?
C1 C2 C3 C4 0.9(5) . . . . ?
C2 C3 C4 C5 0.0(6) . . . . ?
C3 C4 C5 C6 0.0(6) . . . . ?
C2 C1 C6 C5 1.9(5) . . . . ?
N1 C1 C6 C5 -179.9(3) . . . . ?
C2 C1 C6 C7 -178.5(3) . . . . ?
N1 C1 C6 C7 -0.3(3) . . . . ?
C4 C5 C6 C1 -0.9(5) . . . . ?
C4 C5 C6 C7 179.7(4) . . . . ?
C1 C6 C7 C8 -178.7(3) . . . . ?
C5 C6 C7 C8 0.7(6) . . . . ?
C1 C6 C7 C12 0.0(3) . . . . ?
C5 C6 C7 C12 179.4(3) . . . . ?
C12 C7 C8 C9 -0.9(5) . . . . ?
C6 C7 C8 C9 177.7(4) . . . . ?
C7 C8 C9 C10 -0.3(6) . . . . ?
C8 C9 C10 C11 0.6(5) . . . . ?
C9 C10 C11 C12 0.2(4) . . . . ?
C10 C11 C12 N1 -178.5(2) . . . . ?
C10 C11 C12 C7 -1.5(4) . . . . ?
C1 N1 C12 C11 176.8(3) . . . . ?
C13 N1 C12 C11 1.4(4) . . . . ?
C1 N1 C12 C7 -0.6(3) . . . . ?
C13 N1 C12 C7 -175.9(3) . . . . ?
C8 C7 C12 C11 1.8(4) . . . . ?
C6 C7 C12 C11 -177.2(3) . . . . ?
C8 C7 C12 N1 179.3(2) . . . . ?
C6 C7 C12 N1 0.4(3) . . . . ?
C12 N1 C13 C18 -63.3(4) . . . . ?
C1 N1 C13 C18 122.1(3) . . . . ?
C12 N1 C13 C14 117.5(3) . . . . ?
C1 N1 C13 C14 -57.1(4) . . . . ?
C18 C13 C14 C15 1.1(5) . . . . ?
N1 C13 C14 C15 -179.7(3) . . . . ?
C13 C14 C15 C16 0.1(5) . . . . ?
C14 C15 C16 C17 -0.3(5) . . . . ?
C15 C16 C17 C18 -0.8(5) . . . . ?
C14 C13 C18 C17 -2.2(5) . . . . ?
N1 C13 C18 C17 178.6(3) . . . . ?
C16 C17 C18 C13 2.0(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.087
_refine_diff_density_min         -0.084
_refine_diff_density_rms         0.023
