# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1551540'
_audit_update_record             
;
2017-05-22 deposited with the CCDC.
2018-02-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          364
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H13 N3'
_chemical_formula_weight         271.31

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 '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/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.9797(2)
_cell_length_b                   17.5384(3)
_cell_length_c                   9.3882(2)
_cell_angle_alpha                90
_cell_angle_beta                 108.488(2)
_cell_angle_gamma                90
_cell_volume                     1402.24(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    292(2)
_cell_measurement_reflns_used    3222
_cell_measurement_theta_min      5.5560
_cell_measurement_theta_max      71.1950

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_F_000             568
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.612
_shelx_estimated_absorpt_T_min   0.862
_shelx_estimated_absorpt_T_max   0.887
_exptl_absorpt_correction_T_min  0.91012
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      292(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 5.2169
_diffrn_reflns_number            4882
_diffrn_reflns_av_unetI/netI     0.0165
_diffrn_reflns_av_R_equivalents  0.0134
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         5.044
_diffrn_reflns_theta_max         71.220
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             2630
_reflns_number_gt                2329
_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       'CrysAlisPro (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 (L. J. Farrugia, 2001)'
_computing_publication_material  SHELXL-97

_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)+(0.0549P)²+0.1395P] 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     SHELXL
_refine_ls_extinction_coef       0.0030(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2630
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0403
_refine_ls_R_factor_gt           0.0360
_refine_ls_wR_factor_ref         0.1028
_refine_ls_wR_factor_gt          0.0983
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_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_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
N2 N 0.51512(11) 0.54021(6) 0.72972(11) 0.0506(3) Uani 1 1 d . . . . .
N3 N 0.35788(13) 0.57881(7) 0.49389(13) 0.0613(3) Uani 1 1 d . . . . .
N1 N 0.70626(12) 0.48387(6) 0.91438(13) 0.0602(3) Uani 1 1 d . . . . .
C8 C 0.46879(13) 0.40696(6) 0.80603(14) 0.0497(3) Uani 1 1 d . . . . .
C7 C 0.56312(13) 0.47688(7) 0.82060(14) 0.0508(3) Uani 1 1 d . . . . .
C14 C 0.36243(13) 0.55823(6) 0.63065(14) 0.0499(3) Uani 1 1 d . . . . .
C6 C 0.64164(14) 0.59076(7) 0.76825(15) 0.0550(3) Uani 1 1 d . . . . .
C9 C 0.37283(14) 0.38094(7) 0.66739(15) 0.0532(3) Uani 1 1 d . . . . .
H9 H 0.3643 0.4089 0.5810 0.064 Uiso 1 1 calc R U . . .
C15 C 0.23347(15) 0.55679(7) 0.68163(16) 0.0568(3) Uani 1 1 d . . . . .
H15 H 0.2428 0.5425 0.7795 0.068 Uiso 1 1 calc R U . . .
C10 C 0.29018(15) 0.31372(7) 0.65769(17) 0.0605(3) Uani 1 1 d . . . . .
H10 H 0.2264 0.2964 0.5647 0.073 Uiso 1 1 calc R U . . .
C1 C 0.75748(15) 0.55490(8) 0.88335(16) 0.0598(3) Uani 1 1 d . . . . .
C16 C 0.09070(15) 0.57744(8) 0.58059(19) 0.0674(4) Uani 1 1 d . . . . .
H16 H 0.0008 0.5775 0.6095 0.081 Uiso 1 1 calc R U . . .
C13 C 0.48299(18) 0.36350(8) 0.93324(16) 0.0642(3) Uani 1 1 d . . . . .
H13 H 0.5496 0.3794 1.0261 0.077 Uiso 1 1 calc R U . . .
C17 C 0.08234(17) 0.59789(8) 0.43702(18) 0.0703(4) Uani 1 1 d . . . . .
H17 H -0.0132 0.6113 0.3671 0.084 Uiso 1 1 calc R U . . .
C11 C 0.30184(18) 0.27215(8) 0.78546(19) 0.0694(4) Uani 1 1 d . . . . .
H11 H 0.2443 0.2275 0.7789 0.083 Uiso 1 1 calc R U . . .
C5 C 0.66092(18) 0.66276(8) 0.71535(17) 0.0672(4) Uani 1 1 d . . . . .
H5 H 0.5818 0.6864 0.6393 0.081 Uiso 1 1 calc R U . . .
C18 C 0.21743(17) 0.59822(9) 0.39877(17) 0.0694(4) Uani 1 1 d . . . . .
H18 H 0.2112 0.6127 0.3017 0.083 Uiso 1 1 calc R U . . .
C12 C 0.3988(2) 0.29687(8) 0.92265(19) 0.0749(4) Uani 1 1 d . . . . .
H12 H 0.4076 0.2685 1.0086 0.090 Uiso 1 1 calc R U . . .
C2 C 0.90132(18) 0.59165(10) 0.9498(2) 0.0778(4) Uani 1 1 d . . . . .
H2 H 0.9802 0.5689 1.0274 0.093 Uiso 1 1 calc R U . . .
C4 C 0.8051(2) 0.69737(9) 0.7826(2) 0.0793(5) Uani 1 1 d . . . . .
H4 H 0.8237 0.7455 0.7501 0.095 Uiso 1 1 calc R U . . .
C3 C 0.9221(2) 0.66233(10) 0.8967(2) 0.0841(5) Uani 1 1 d . . . . .
H3 H 1.0173 0.6874 0.9384 0.101 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
N2 C7 1.3835(16) . ?
N2 C6 1.3953(15) . ?
N2 C14 1.4269(15) . ?
N3 C14 1.3218(17) . ?
N3 C18 1.3378(18) . ?
N1 C7 1.3133(16) . ?
N1 C1 1.3904(18) . ?
C8 C13 1.3881(18) . ?
C8 C9 1.3905(17) . ?
C8 C7 1.4720(16) . ?
C14 C15 1.3865(17) . ?
C6 C5 1.3877(19) . ?
C6 C1 1.3901(19) . ?
C9 C10 1.3807(18) . ?
C9 H9 0.9300 . ?
C15 C16 1.3796(19) . ?
C15 H15 0.9300 . ?
C10 C11 1.379(2) . ?
C10 H10 0.9300 . ?
C1 C2 1.4008(19) . ?
C16 C17 1.374(2) . ?
C16 H16 0.9300 . ?
C13 C12 1.378(2) . ?
C13 H13 0.9300 . ?
C17 C18 1.370(2) . ?
C17 H17 0.9300 . ?
C11 C12 1.376(2) . ?
C11 H11 0.9300 . ?
C5 C4 1.387(2) . ?
C5 H5 0.9300 . ?
C18 H18 0.9300 . ?
C12 H12 0.9300 . ?
C2 C3 1.371(3) . ?
C2 H2 0.9300 . ?
C4 C3 1.384(3) . ?
C4 H4 0.9300 . ?
C3 H3 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
C7 N2 C6 106.34(10) . . ?
C7 N2 C14 128.82(10) . . ?
C6 N2 C14 124.29(10) . . ?
C14 N3 C18 116.75(12) . . ?
C7 N1 C1 105.16(11) . . ?
C13 C8 C9 119.06(12) . . ?
C13 C8 C7 118.97(11) . . ?
C9 C8 C7 121.86(11) . . ?
N1 C7 N2 112.70(11) . . ?
N1 C7 C8 123.51(11) . . ?
N2 C7 C8 123.64(11) . . ?
N3 C14 C15 124.63(12) . . ?
N3 C14 N2 114.90(10) . . ?
C15 C14 N2 120.40(11) . . ?
C5 C6 C1 122.84(12) . . ?
C5 C6 N2 132.00(13) . . ?
C1 C6 N2 105.13(11) . . ?
C10 C9 C8 120.17(12) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C16 C15 C14 116.98(13) . . ?
C16 C15 H15 121.5 . . ?
C14 C15 H15 121.5 . . ?
C11 C10 C9 120.21(13) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C6 C1 N1 110.64(11) . . ?
C6 C1 C2 119.67(14) . . ?
N1 C1 C2 129.68(14) . . ?
C17 C16 C15 119.54(13) . . ?
C17 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
C12 C13 C8 120.32(14) . . ?
C12 C13 H13 119.8 . . ?
C8 C13 H13 119.8 . . ?
C18 C17 C16 118.74(13) . . ?
C18 C17 H17 120.6 . . ?
C16 C17 H17 120.6 . . ?
C12 C11 C10 119.89(13) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C4 C5 C6 116.08(15) . . ?
C4 C5 H5 122.0 . . ?
C6 C5 H5 122.0 . . ?
N3 C18 C17 123.35(15) . . ?
N3 C18 H18 118.3 . . ?
C17 C18 H18 118.3 . . ?
C11 C12 C13 120.30(14) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C3 C2 C1 117.81(16) . . ?
C3 C2 H2 121.1 . . ?
C1 C2 H2 121.1 . . ?
C3 C4 C5 121.84(15) . . ?
C3 C4 H4 119.1 . . ?
C5 C4 H4 119.1 . . ?
C2 C3 C4 121.74(14) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?

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 N1 C7 N2 -0.86(14) . . . . ?
C1 N1 C7 C8 174.77(11) . . . . ?
C6 N2 C7 N1 1.42(14) . . . . ?
C14 N2 C7 N1 -170.22(11) . . . . ?
C6 N2 C7 C8 -174.21(11) . . . . ?
C14 N2 C7 C8 14.15(19) . . . . ?
C13 C8 C7 N1 35.17(17) . . . . ?
C9 C8 C7 N1 -141.09(13) . . . . ?
C13 C8 C7 N2 -149.67(12) . . . . ?
C9 C8 C7 N2 34.07(17) . . . . ?
C18 N3 C14 C15 -1.16(19) . . . . ?
C18 N3 C14 N2 -178.20(11) . . . . ?
C7 N2 C14 N3 -130.82(13) . . . . ?
C6 N2 C14 N3 58.90(16) . . . . ?
C7 N2 C14 C15 52.00(17) . . . . ?
C6 N2 C14 C15 -118.28(13) . . . . ?
C7 N2 C6 C5 -179.71(14) . . . . ?
C14 N2 C6 C5 -7.6(2) . . . . ?
C7 N2 C6 C1 -1.31(13) . . . . ?
C14 N2 C6 C1 170.80(11) . . . . ?
C13 C8 C9 C10 1.56(18) . . . . ?
C7 C8 C9 C10 177.82(11) . . . . ?
N3 C14 C15 C16 0.93(19) . . . . ?
N2 C14 C15 C16 177.82(11) . . . . ?
C8 C9 C10 C11 0.25(18) . . . . ?
C5 C6 C1 N1 179.44(12) . . . . ?
N2 C6 C1 N1 0.86(14) . . . . ?
C5 C6 C1 C2 -0.5(2) . . . . ?
N2 C6 C1 C2 -179.08(12) . . . . ?
C7 N1 C1 C6 -0.03(15) . . . . ?
C7 N1 C1 C2 179.90(15) . . . . ?
C14 C15 C16 C17 0.17(19) . . . . ?
C9 C8 C13 C12 -2.2(2) . . . . ?
C7 C8 C13 C12 -178.58(12) . . . . ?
C15 C16 C17 C18 -0.9(2) . . . . ?
C9 C10 C11 C12 -1.4(2) . . . . ?
C1 C6 C5 C4 1.0(2) . . . . ?
N2 C6 C5 C4 179.16(13) . . . . ?
C14 N3 C18 C17 0.3(2) . . . . ?
C16 C17 C18 N3 0.7(2) . . . . ?
C10 C11 C12 C13 0.8(2) . . . . ?
C8 C13 C12 C11 1.1(2) . . . . ?
C6 C1 C2 C3 -0.4(2) . . . . ?
N1 C1 C2 C3 179.63(15) . . . . ?
C6 C5 C4 C3 -0.6(2) . . . . ?
C1 C2 C3 C4 0.8(3) . . . . ?
C5 C4 C3 C2 -0.3(3) . . . . ?

_refine_diff_density_max         0.158
_refine_diff_density_min         -0.135
_refine_diff_density_rms         0.026

_shelxl_version_number           2013-4


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetone'
