# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_I
_audit_block_doi                 10.5517/ccdc.csd.cc1lwcsm
_database_code_depnum_ccdc_archive 'CCDC 1486071'
_audit_update_record             
;
2016-06-16 deposited with the CCDC.
2017-07-13 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            'C16 H11 N3'
_chemical_formula_weight         245.28

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                   11.280(3)
_cell_length_b                   12.342(4)
_cell_length_c                   8.977(3)
_cell_angle_alpha                90
_cell_angle_beta                 97.198(8)
_cell_angle_gamma                90
_cell_volume                     1239.8(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2544
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      27.99

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_F_000             512
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.081
_shelx_estimated_absorpt_T_min   0.977
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6925
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'SADABS-2012/1 (Bruker,2012)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker Kappa APEX-Duo CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8335
_diffrn_reflns_av_unetI/netI     0.0256
_diffrn_reflns_av_R_equivalents  0.0228
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.820
_diffrn_reflns_theta_max         28.253
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.952
_diffrn_measured_fraction_theta_full 0.965
_diffrn_reflns_Laue_measured_fraction_max 0.952
_diffrn_reflns_Laue_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.952
_diffrn_reflns_point_group_measured_fraction_full 0.965
_reflns_number_total             2913
_reflns_number_gt                1861
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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     
'w=1/[σ²(Fo²)+(0.0635P)²+0.0815P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2913
_refine_ls_number_parameters     216
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0693
_refine_ls_R_factor_gt           0.0389
_refine_ls_wR_factor_ref         0.1240
_refine_ls_wR_factor_gt          0.1029
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.012
_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
C1 C 0.31680(11) 0.84839(10) 0.15285(15) 0.0484(3) Uani 1 1 d . . . . .
N1 N 0.23349(10) 0.76754(8) 0.08956(14) 0.0528(3) Uani 1 1 d . . . . .
C2 C 0.43506(11) 0.84938(10) 0.11485(14) 0.0456(3) Uani 1 1 d . . . . .
N2 N 0.24752(11) 0.66119(10) 0.12968(17) 0.0666(4) Uani 1 1 d . . . . .
C3 C 0.47754(13) 0.77611(11) 0.01221(16) 0.0532(3) Uani 1 1 d . . . . .
H3 H 0.4208(12) 0.7222(11) -0.0377(17) 0.059(4) Uiso 1 1 d . . . . .
N3 N 0.15489(11) 0.60731(10) 0.06941(17) 0.0697(4) Uani 1 1 d . . . . .
C4 C 0.59272(13) 0.78313(13) -0.01925(18) 0.0606(4) Uani 1 1 d . . . . .
H4 H 0.6221(14) 0.7316(13) -0.0923(19) 0.073(5) Uiso 1 1 d . . . . .
C5 C 0.67065(13) 0.86194(13) 0.04992(19) 0.0625(4) Uani 1 1 d . . . . .
H5 H 0.7551(14) 0.8662(12) 0.0264(17) 0.073(5) Uiso 1 1 d . . . . .
C6 C 0.63265(13) 0.93352(13) 0.14818(17) 0.0585(4) Uani 1 1 d . . . . .
H6 H 0.6861(14) 0.9913(13) 0.1942(19) 0.073(5) Uiso 1 1 d . . . . .
C7 C 0.51349(12) 0.93019(10) 0.18330(15) 0.0490(3) Uani 1 1 d . . . . .
C8 C 0.47173(15) 1.00556(12) 0.28300(18) 0.0612(4) Uani 1 1 d . . . . .
H8 H 0.5262(13) 1.0590(13) 0.3243(18) 0.067(4) Uiso 1 1 d . . . . .
C9 C 0.35669(15) 1.00228(13) 0.31426(19) 0.0655(4) Uani 1 1 d . . . . .
H9 H 0.3287(14) 1.0533(14) 0.379(2) 0.080(5) Uiso 1 1 d . . . . .
C10 C 0.27850(13) 0.92258(12) 0.24852(17) 0.0579(4) Uani 1 1 d . . . . .
H10 H 0.1981(13) 0.9173(12) 0.2711(16) 0.064(4) Uiso 1 1 d . . . . .
C11 C 0.12717(11) 0.78167(11) 0.00159(16) 0.0500(3) Uani 1 1 d . . . . .
C12 C 0.07164(13) 0.87142(14) -0.07008(19) 0.0626(4) Uani 1 1 d . . . . .
H12 H 0.1103(15) 0.9445(15) -0.059(2) 0.082(5) Uiso 1 1 d . . . . .
C13 C -0.03618(15) 0.85240(17) -0.1544(2) 0.0792(5) Uani 1 1 d . . . . .
H13 H -0.0793(15) 0.9105(15) -0.209(2) 0.081(5) Uiso 1 1 d . . . . .
C14 C -0.08809(16) 0.74904(19) -0.1664(3) 0.0839(6) Uani 1 1 d . . . . .
H14 H -0.160(2) 0.7432(16) -0.230(3) 0.110(7) Uiso 1 1 d . . . . .
C15 C -0.03378(15) 0.66119(16) -0.0966(2) 0.0754(5) Uani 1 1 d . . . . .
H15 H -0.0675(16) 0.5897(17) -0.102(2) 0.098(6) Uiso 1 1 d . . . . .
C16 C 0.07726(12) 0.67847(12) -0.01078(18) 0.0574(4) Uani 1 1 d . . . . .


_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
C1 C10 1.362(2) . ?
C1 C2 1.4178(18) . ?
C1 N1 1.4380(17) . ?
N1 C11 1.3620(18) . ?
N1 N2 1.3650(16) . ?
C2 C3 1.4166(19) . ?
C2 C7 1.4208(18) . ?
N2 N3 1.2981(18) . ?
C3 C4 1.366(2) . ?
C3 H3 0.990(15) . ?
N3 C16 1.378(2) . ?
C4 C5 1.403(2) . ?
C4 H4 1.000(17) . ?
C5 C6 1.355(2) . ?
C5 H5 1.003(15) . ?
C6 C7 1.4191(19) . ?
C6 H6 0.990(17) . ?
C7 C8 1.412(2) . ?
C8 C9 1.362(2) . ?
C8 H8 0.945(16) . ?
C9 C10 1.401(2) . ?
C9 H9 0.937(17) . ?
C10 H10 0.956(14) . ?
C11 C12 1.390(2) . ?
C11 C16 1.3913(19) . ?
C12 C13 1.370(2) . ?
C12 H12 1.001(17) . ?
C13 C14 1.402(3) . ?
C13 H13 0.966(18) . ?
C14 C15 1.359(3) . ?
C14 H14 0.94(2) . ?
C15 C16 1.402(2) . ?
C15 H15 0.96(2) . ?

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 C1 C2 121.88(13) . . ?
C10 C1 N1 118.19(12) . . ?
C2 C1 N1 119.93(12) . . ?
C11 N1 N2 109.92(11) . . ?
C11 N1 C1 128.65(11) . . ?
N2 N1 C1 120.97(11) . . ?
C3 C2 C1 123.79(12) . . ?
C3 C2 C7 119.10(12) . . ?
C1 C2 C7 117.11(12) . . ?
N3 N2 N1 108.78(12) . . ?
C4 C3 C2 120.12(13) . . ?
C4 C3 H3 121.8(8) . . ?
C2 C3 H3 118.1(8) . . ?
N2 N3 C16 108.48(12) . . ?
C3 C4 C5 120.79(14) . . ?
C3 C4 H4 119.8(9) . . ?
C5 C4 H4 119.4(9) . . ?
C6 C5 C4 120.55(14) . . ?
C6 C5 H5 119.3(9) . . ?
C4 C5 H5 120.1(9) . . ?
C5 C6 C7 120.75(14) . . ?
C5 C6 H6 121.0(9) . . ?
C7 C6 H6 118.2(9) . . ?
C8 C7 C6 121.48(13) . . ?
C8 C7 C2 119.83(12) . . ?
C6 C7 C2 118.69(13) . . ?
C9 C8 C7 120.87(15) . . ?
C9 C8 H8 122.0(9) . . ?
C7 C8 H8 117.1(9) . . ?
C8 C9 C10 119.99(15) . . ?
C8 C9 H9 120.7(10) . . ?
C10 C9 H9 119.3(10) . . ?
C1 C10 C9 120.32(13) . . ?
C1 C10 H10 118.2(9) . . ?
C9 C10 H10 121.5(9) . . ?
N1 C11 C12 133.11(13) . . ?
N1 C11 C16 104.31(12) . . ?
C12 C11 C16 122.55(14) . . ?
C13 C12 C11 115.89(16) . . ?
C13 C12 H12 123.7(10) . . ?
C11 C12 H12 120.4(10) . . ?
C12 C13 C14 122.12(19) . . ?
C12 C13 H13 120.7(10) . . ?
C14 C13 H13 117.2(10) . . ?
C15 C14 C13 122.05(18) . . ?
C15 C14 H14 121.8(13) . . ?
C13 C14 H14 116.1(13) . . ?
C14 C15 C16 116.87(17) . . ?
C14 C15 H15 123.8(12) . . ?
C16 C15 H15 119.4(12) . . ?
N3 C16 C11 108.51(13) . . ?
N3 C16 C15 130.97(15) . . ?
C11 C16 C15 120.51(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
C10 C1 N1 C11 60.27(18) . . . . ?
C2 C1 N1 C11 -119.62(15) . . . . ?
C10 C1 N1 N2 -111.12(15) . . . . ?
C2 C1 N1 N2 68.99(16) . . . . ?
C10 C1 C2 C3 -177.86(13) . . . . ?
N1 C1 C2 C3 2.03(19) . . . . ?
C10 C1 C2 C7 1.21(19) . . . . ?
N1 C1 C2 C7 -178.91(11) . . . . ?
C11 N1 N2 N3 0.62(16) . . . . ?
C1 N1 N2 N3 173.48(12) . . . . ?
C1 C2 C3 C4 179.45(13) . . . . ?
C7 C2 C3 C4 0.4(2) . . . . ?
N1 N2 N3 C16 -0.62(16) . . . . ?
C2 C3 C4 C5 0.5(2) . . . . ?
C3 C4 C5 C6 -0.7(2) . . . . ?
C4 C5 C6 C7 0.1(2) . . . . ?
C5 C6 C7 C8 -178.66(14) . . . . ?
C5 C6 C7 C2 0.8(2) . . . . ?
C3 C2 C7 C8 178.43(12) . . . . ?
C1 C2 C7 C8 -0.68(18) . . . . ?
C3 C2 C7 C6 -1.03(18) . . . . ?
C1 C2 C7 C6 179.87(11) . . . . ?
C6 C7 C8 C9 179.16(14) . . . . ?
C2 C7 C8 C9 -0.3(2) . . . . ?
C7 C8 C9 C10 0.8(2) . . . . ?
C2 C1 C10 C9 -0.8(2) . . . . ?
N1 C1 C10 C9 179.35(13) . . . . ?
C8 C9 C10 C1 -0.2(2) . . . . ?
N2 N1 C11 C12 -178.56(15) . . . . ?
C1 N1 C11 C12 9.3(2) . . . . ?
N2 N1 C11 C16 -0.35(15) . . . . ?
C1 N1 C11 C16 -172.50(12) . . . . ?
N1 C11 C12 C13 178.00(15) . . . . ?
C16 C11 C12 C13 0.1(2) . . . . ?
C11 C12 C13 C14 0.7(3) . . . . ?
C12 C13 C14 C15 -0.9(3) . . . . ?
C13 C14 C15 C16 0.3(3) . . . . ?
N2 N3 C16 C11 0.41(16) . . . . ?
N2 N3 C16 C15 179.34(15) . . . . ?
N1 C11 C16 N3 -0.03(15) . . . . ?
C12 C11 C16 N3 178.43(13) . . . . ?
N1 C11 C16 C15 -179.09(13) . . . . ?
C12 C11 C16 C15 -0.6(2) . . . . ?
C14 C15 C16 N3 -178.37(16) . . . . ?
C14 C15 C16 C11 0.5(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C15 H15 N3 0.96(2) 2.65(2) 3.604(2) 170.5(16) 3_565

_refine_diff_density_max         0.118
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.030
