# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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 1944062'
_audit_update_record             
;
2019-07-30 deposited with the CCDC.	2019-12-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H15 N3'
_chemical_formula_weight         333.38

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/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                   9.549(2)
_cell_length_b                   21.299(4)
_cell_length_c                   9.583(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 111.20(3)
_cell_angle_gamma                90.00
_cell_volume                     1817.1(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2581
_cell_measurement_theta_min      1.912
_cell_measurement_theta_max      23.259

_exptl_crystal_description       Needle
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.219
_exptl_crystal_F_000             696
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.07
_exptl_absorpt_coefficient_mu    0.073
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.6319
_exptl_absorpt_correction_T_max  0.7954
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker SMART APEX'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17692
_diffrn_reflns_av_unetI/netI     0.0562
_diffrn_reflns_av_R_equivalents  0.0917
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.912
_diffrn_reflns_theta_max         23.259
_diffrn_reflns_theta_full        23.259
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             2581
_reflns_number_gt                1506
_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-2014/7 (Sheldrick, 2014)'
_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)+(0.0717P)²+0.1023P] 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-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.016(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2581
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0897
_refine_ls_R_factor_gt           0.0495
_refine_ls_wR_factor_ref         0.1548
_refine_ls_wR_factor_gt          0.1274
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_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
N2 N 0.8323(2) 0.46120(8) 0.6549(2) 0.0639(6) Uani 1 1 d . . . . .
N3 N 0.3851(2) 0.36731(11) 0.3227(3) 0.0810(7) Uani 1 1 d . . . . .
C9 C 0.9373(3) 0.50914(11) 0.6924(3) 0.0616(7) Uani 1 1 d . . . . .
C3 C 0.6025(3) 0.41539(11) 0.4751(3) 0.0654(7) Uani 1 1 d . . . . .
C10 C 0.9336(3) 0.56100(11) 0.5930(3) 0.0664(7) Uani 1 1 d . . . . .
C8 C 0.7183(3) 0.46425(11) 0.5192(3) 0.0628(7) Uani 1 1 d . . . . .
C7 C 0.7030(3) 0.51491(12) 0.4106(3) 0.0689(7) Uani 1 1 d . . . . .
N1 N 0.7301(3) 0.30856(12) 0.8084(3) 0.1040(9) Uani 1 1 d . . . . .
C4 C 0.4816(3) 0.41930(13) 0.3361(3) 0.0739(8) Uani 1 1 d . . . . .
C2 C 0.5769(3) 0.35821(12) 0.5476(3) 0.0717(7) Uani 1 1 d . . . . .
C15 C 1.0545(3) 0.50840(12) 0.8385(3) 0.0751(8) Uani 1 1 d . . . . .
H15 H 1.0609 0.4748 0.9025 0.090 Uiso 1 1 calc R U . . .
C17 C 0.2564(3) 0.33253(11) 0.0524(3) 0.0754(8) Uani 1 1 d . . . . .
C11 C 0.8142(3) 0.56201(11) 0.4519(3) 0.0721(8) Uani 1 1 d . . . . .
H11 H 0.8092 0.5944 0.3852 0.087 Uiso 1 1 calc R U . . .
C1 C 0.6651(3) 0.33217(12) 0.6922(4) 0.0789(8) Uani 1 1 d . . . . .
C23 C 0.4437(3) 0.33113(13) 0.4494(4) 0.0813(8) Uani 1 1 d . . . . .
H23 H 0.4014 0.2941 0.4674 0.098 Uiso 1 1 calc R U . . .
C6 C 0.5750(3) 0.51543(13) 0.2679(3) 0.0837(8) Uani 1 1 d . . . . .
H6 H 0.5668 0.5480 0.2008 0.100 Uiso 1 1 calc R U . . .
C12 C 1.0473(3) 0.60959(12) 0.6441(3) 0.0798(8) Uani 1 1 d . . . . .
H12 H 1.0470 0.6424 0.5800 0.096 Uiso 1 1 calc R U . . .
C5 C 0.4662(3) 0.46919(13) 0.2298(3) 0.0867(9) Uani 1 1 d . . . . .
H5 H 0.3859 0.4702 0.1388 0.104 Uiso 1 1 calc R U . . .
C14 C 1.1578(3) 0.55684(13) 0.8850(3) 0.0865(9) Uani 1 1 d . . . . .
H14 H 1.2294 0.5565 0.9814 0.104 Uiso 1 1 calc R U . . .
C22 C 0.3927(4) 0.31666(13) 0.0379(4) 0.0947(10) Uani 1 1 d . . . . .
H22 H 0.4822 0.3214 0.1190 0.114 Uiso 1 1 calc R U . . .
C13 C 1.1551(3) 0.60807(13) 0.7849(4) 0.0883(9) Uani 1 1 d . . . . .
H13 H 1.2263 0.6399 0.8160 0.106 Uiso 1 1 calc R U . . .
C18 C 0.1226(4) 0.32588(12) -0.0735(4) 0.0898(9) Uani 1 1 d . . . . .
H18 H 0.0314 0.3370 -0.0660 0.108 Uiso 1 1 calc R U . . .
C16 C 0.2413(3) 0.35564(14) 0.1975(3) 0.0912(9) Uani 1 1 d . . . . .
H16A H 0.1835 0.3943 0.1765 0.109 Uiso 1 1 calc R U . . .
H16B H 0.1846 0.3248 0.2296 0.109 Uiso 1 1 calc R U . . .
C21 C 0.3950(5) 0.29335(15) -0.0998(5) 0.1154(12) Uani 1 1 d . . . . .
H21 H 0.4857 0.2828 -0.1090 0.138 Uiso 1 1 calc R U . . .
C20 C 0.2595(7) 0.28620(16) -0.2224(5) 0.1221(15) Uani 1 1 d . . . . .
H20 H 0.2603 0.2702 -0.3125 0.146 Uiso 1 1 calc R U . . .
C19 C 0.1250(6) 0.30300(16) -0.2088(4) 0.1173(12) Uani 1 1 d . . . . .
H19 H 0.0356 0.2990 -0.2904 0.141 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 C8 1.362(3) . ?
N2 C9 1.384(3) . ?
N3 C23 1.375(3) . ?
N3 C4 1.416(3) . ?
N3 C16 1.481(3) . ?
C9 C15 1.442(3) . ?
C9 C10 1.451(3) . ?
C3 C4 1.415(3) . ?
C3 C8 1.465(3) . ?
C3 C2 1.466(3) . ?
C10 C11 1.419(3) . ?
C10 C12 1.451(4) . ?
C8 C7 1.469(3) . ?
C7 C11 1.410(3) . ?
C7 C6 1.468(3) . ?
N1 C1 1.173(3) . ?
C4 C5 1.443(4) . ?
C2 C23 1.403(4) . ?
C2 C1 1.447(4) . ?
C15 C14 1.384(3) . ?
C15 H15 0.9300 . ?
C17 C22 1.400(4) . ?
C17 C18 1.411(4) . ?
C17 C16 1.531(4) . ?
C11 H11 0.9300 . ?
C23 H23 0.9300 . ?
C6 C5 1.381(4) . ?
C6 H6 0.9300 . ?
C12 C13 1.369(4) . ?
C12 H12 0.9300 . ?
C5 H5 0.9300 . ?
C14 C13 1.447(4) . ?
C14 H14 0.9300 . ?
C22 C21 1.417(4) . ?
C22 H22 0.9300 . ?
C13 H13 0.9300 . ?
C18 C19 1.392(5) . ?
C18 H18 0.9300 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C21 C20 1.406(5) . ?
C21 H21 0.9300 . ?
C20 C19 1.385(5) . ?
C20 H20 0.9300 . ?
C19 H19 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
C8 N2 C9 117.8(2) . . ?
C23 N3 C4 108.3(2) . . ?
C23 N3 C16 125.7(3) . . ?
C4 N3 C16 125.9(3) . . ?
N2 C9 C15 118.6(2) . . ?
N2 C9 C10 123.2(2) . . ?
C15 C9 C10 118.1(2) . . ?
C4 C3 C8 120.2(2) . . ?
C4 C3 C2 106.0(2) . . ?
C8 C3 C2 133.8(2) . . ?
C11 C10 C9 117.2(2) . . ?
C11 C10 C12 123.8(2) . . ?
C9 C10 C12 119.0(2) . . ?
N2 C8 C3 120.0(2) . . ?
N2 C8 C7 123.5(2) . . ?
C3 C8 C7 116.5(2) . . ?
C11 C7 C6 123.0(2) . . ?
C11 C7 C8 116.9(2) . . ?
C6 C7 C8 120.1(2) . . ?
C3 C4 N3 108.8(2) . . ?
C3 C4 C5 123.3(3) . . ?
N3 C4 C5 127.9(3) . . ?
C23 C2 C1 123.9(3) . . ?
C23 C2 C3 106.9(2) . . ?
C1 C2 C3 129.3(2) . . ?
C14 C15 C9 121.1(3) . . ?
C14 C15 H15 119.4 . . ?
C9 C15 H15 119.4 . . ?
C22 C17 C18 118.5(3) . . ?
C22 C17 C16 124.4(3) . . ?
C18 C17 C16 117.1(3) . . ?
C7 C11 C10 121.4(2) . . ?
C7 C11 H11 119.3 . . ?
C10 C11 H11 119.3 . . ?
N1 C1 C2 176.1(3) . . ?
N3 C23 C2 110.0(3) . . ?
N3 C23 H23 125.0 . . ?
C2 C23 H23 125.0 . . ?
C5 C6 C7 122.3(3) . . ?
C5 C6 H6 118.9 . . ?
C7 C6 H6 118.9 . . ?
C13 C12 C10 121.3(3) . . ?
C13 C12 H12 119.3 . . ?
C10 C12 H12 119.3 . . ?
C6 C5 C4 117.6(3) . . ?
C6 C5 H5 121.2 . . ?
C4 C5 H5 121.2 . . ?
C15 C14 C13 120.6(3) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C17 C22 C21 120.3(3) . . ?
C17 C22 H22 119.8 . . ?
C21 C22 H22 119.8 . . ?
C12 C13 C14 119.9(3) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C19 C18 C17 121.1(3) . . ?
C19 C18 H18 119.4 . . ?
C17 C18 H18 119.4 . . ?
N3 C16 C17 115.2(2) . . ?
N3 C16 H16A 108.5 . . ?
C17 C16 H16A 108.5 . . ?
N3 C16 H16B 108.5 . . ?
C17 C16 H16B 108.5 . . ?
H16A C16 H16B 107.5 . . ?
C20 C21 C22 119.8(4) . . ?
C20 C21 H21 120.1 . . ?
C22 C21 H21 120.1 . . ?
C19 C20 C21 119.8(4) . . ?
C19 C20 H20 120.1 . . ?
C21 C20 H20 120.1 . . ?
C20 C19 C18 120.4(4) . . ?
C20 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?

_refine_diff_density_max         0.145
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.035

