# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 1904622'
loop_
_audit_author_name
_audit_author_address
'Liang Taoyuan'
;South China University of Technology
China
;
_audit_update_record             
;
2019-03-21 deposited with the CCDC.	2019-04-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H15 N3 O'
_chemical_formula_sum            'C18 H15 N3 O'
_chemical_formula_weight         289.33

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   9.405(7)
_cell_length_b                   9.471(7)
_cell_length_c                   9.815(7)
_cell_angle_alpha                84.218(8)
_cell_angle_beta                 63.798(7)
_cell_angle_gamma                78.437(8)
_cell_volume                     768.5(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5185
_cell_measurement_theta_min      2.992
_cell_measurement_theta_max      25.027

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            YELLOW
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.250
_exptl_crystal_F_000             304
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.19
_exptl_absorpt_coefficient_mu    0.080
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   NONE
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7291
_diffrn_reflns_av_unetI/netI     0.0154
_diffrn_reflns_av_R_equivalents  0.0208
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.992
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.970
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.970
_reflns_number_total             2702
_reflns_number_gt                2433
_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 (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)+(0.0719P)²+0.1393P] 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       0.102(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2702
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0395
_refine_ls_wR_factor_ref         0.1250
_refine_ls_wR_factor_gt          0.1204
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_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
O1 O 0.4919(3) 0.42968(15) 0.3142(3) 0.1357(8) Uani 1 1 d . . . . .
N1 N 0.17065(14) 0.71997(11) 0.17667(13) 0.0491(3) Uani 1 1 d . . . . .
N2 N 0.36128(15) 0.78301(13) 0.20766(16) 0.0592(4) Uani 1 1 d . . . . .
N3 N 0.24321(16) 0.83306(12) 0.17181(16) 0.0604(4) Uani 1 1 d . . . . .
C1 C -0.13904(19) 0.88659(16) 0.36528(17) 0.0573(4) Uani 1 1 d . . . . .
H1A H -0.0847 0.8296 0.4164 0.069 Uiso 1 1 calc R U . . .
C2 C -0.2651(2) 0.99602(19) 0.4410(2) 0.0731(5) Uani 1 1 d . . . . .
H2A H -0.2956 1.0121 0.5429 0.088 Uiso 1 1 calc R U . . .
C3 C -0.3453(2) 1.08096(19) 0.3659(2) 0.0805(6) Uani 1 1 d . . . . .
H3A H -0.4292 1.1551 0.4167 0.097 Uiso 1 1 calc R U . . .
C4 C -0.3017(2) 1.05658(19) 0.2166(2) 0.0756(5) Uani 1 1 d . . . . .
H4A H -0.3571 1.1136 0.1665 0.091 Uiso 1 1 calc R U . . .
C5 C -0.17654(18) 0.94833(16) 0.13987(19) 0.0599(4) Uani 1 1 d . . . . .
H5A H -0.1474 0.9331 0.0381 0.072 Uiso 1 1 calc R U . . .
C6 C -0.09348(16) 0.86163(13) 0.21367(16) 0.0478(3) Uani 1 1 d . . . . .
C7 C 0.04187(17) 0.74659(14) 0.13001(16) 0.0498(3) Uani 1 1 d . . . . .
C8 C 0.0565(2) 0.67140(18) 0.0177(2) 0.0714(5) Uani 1 1 d . . . . .
H8A H 0.1482 0.6028 -0.0298 0.086 Uiso 1 1 calc R U . . .
H8B H -0.0250 0.6867 -0.0142 0.086 Uiso 1 1 calc R U . . .
C9 C 0.02830(18) 0.44644(15) 0.32347(15) 0.0518(4) Uani 1 1 d . . . . .
H9A H -0.0464 0.5280 0.3692 0.062 Uiso 1 1 calc R U . . .
C10 C -0.0208(2) 0.31471(17) 0.34152(18) 0.0630(4) Uani 1 1 d . . . . .
H10A H -0.1284 0.3077 0.4000 0.076 Uiso 1 1 calc R U . . .
C11 C 0.0892(2) 0.19389(17) 0.2732(2) 0.0677(5) Uani 1 1 d . . . . .
H11A H 0.0555 0.1057 0.2854 0.081 Uiso 1 1 calc R U . . .
C12 C 0.2481(2) 0.20328(16) 0.1873(2) 0.0663(4) Uani 1 1 d . . . . .
H12A H 0.3219 0.1213 0.1414 0.080 Uiso 1 1 calc R U . . .
C13 C 0.29939(19) 0.33385(15) 0.16851(17) 0.0567(4) Uani 1 1 d . . . . .
H13A H 0.4074 0.3395 0.1102 0.068 Uiso 1 1 calc R U . . .
C14 C 0.18961(16) 0.45670(13) 0.23675(15) 0.0451(3) Uani 1 1 d . . . . .
C15 C 0.24409(15) 0.59614(13) 0.21720(15) 0.0449(3) Uani 1 1 d . . . . .
C16 C 0.36701(16) 0.63830(14) 0.23654(16) 0.0512(4) Uani 1 1 d . . . . .
C17 C 0.4887(2) 0.55595(18) 0.2839(2) 0.0693(5) Uani 1 1 d . . . . .
C18 C 0.6073(2) 0.6330(2) 0.2910(3) 0.0904(6) Uani 1 1 d . . . . .
H18A H 0.5861 0.7324 0.2632 0.136 Uiso 1 1 calc R U . . .
H18B H 0.5988 0.6266 0.3925 0.136 Uiso 1 1 calc R U . . .
H18C H 0.7138 0.5899 0.2221 0.136 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
O1 C17 1.201(2) . ?
N1 C15 1.3544(18) . ?
N1 N3 1.3672(17) . ?
N1 C7 1.4439(19) . ?
N2 N3 1.2970(19) . ?
N2 C16 1.366(2) . ?
C1 C2 1.385(2) . ?
C1 C6 1.386(2) . ?
C1 H1A 0.9300 . ?
C2 C3 1.374(3) . ?
C2 H2A 0.9300 . ?
C3 C4 1.367(3) . ?
C3 H3A 0.9300 . ?
C4 C5 1.376(2) . ?
C4 H4A 0.9300 . ?
C5 C6 1.390(2) . ?
C5 H5A 0.9300 . ?
C6 C7 1.477(2) . ?
C7 C8 1.314(2) . ?
C8 H8A 0.9300 . ?
C8 H8B 0.9300 . ?
C9 C10 1.384(2) . ?
C9 C14 1.392(2) . ?
C9 H9A 0.9300 . ?
C10 C11 1.377(3) . ?
C10 H10A 0.9300 . ?
C11 C12 1.371(3) . ?
C11 H11A 0.9300 . ?
C12 C13 1.382(2) . ?
C12 H12A 0.9300 . ?
C13 C14 1.390(2) . ?
C13 H13A 0.9300 . ?
C14 C15 1.475(2) . ?
C15 C16 1.388(2) . ?
C16 C17 1.474(2) . ?
C17 C18 1.479(3) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?

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
C15 N1 N3 110.94(12) . . ?
C15 N1 C7 131.01(11) . . ?
N3 N1 C7 117.89(11) . . ?
N3 N2 C16 109.25(11) . . ?
N2 N3 N1 107.39(11) . . ?
C2 C1 C6 120.26(15) . . ?
C2 C1 H1A 119.9 . . ?
C6 C1 H1A 119.9 . . ?
C1 C2 C3 120.11(18) . . ?
C1 C2 H2A 119.9 . . ?
C3 C2 H2A 119.9 . . ?
C4 C3 C2 120.01(16) . . ?
C4 C3 H3A 120.0 . . ?
C2 C3 H3A 120.0 . . ?
C3 C4 C5 120.51(16) . . ?
C3 C4 H4A 119.7 . . ?
C5 C4 H4A 119.7 . . ?
C4 C5 C6 120.35(16) . . ?
C4 C5 H5A 119.8 . . ?
C6 C5 H5A 119.8 . . ?
C5 C6 C1 118.76(14) . . ?
C5 C6 C7 119.99(14) . . ?
C1 C6 C7 121.25(12) . . ?
C8 C7 N1 118.51(14) . . ?
C8 C7 C6 126.50(14) . . ?
N1 C7 C6 114.97(12) . . ?
C7 C8 H8A 120.0 . . ?
C7 C8 H8B 120.0 . . ?
H8A C8 H8B 120.0 . . ?
C10 C9 C14 119.89(14) . . ?
C10 C9 H9A 120.1 . . ?
C14 C9 H9A 120.1 . . ?
C11 C10 C9 120.26(16) . . ?
C11 C10 H10A 119.9 . . ?
C9 C10 H10A 119.9 . . ?
C12 C11 C10 120.17(14) . . ?
C12 C11 H11A 119.9 . . ?
C10 C11 H11A 119.9 . . ?
C11 C12 C13 120.36(15) . . ?
C11 C12 H12A 119.8 . . ?
C13 C12 H12A 119.8 . . ?
C12 C13 C14 120.06(15) . . ?
C12 C13 H13A 120.0 . . ?
C14 C13 H13A 120.0 . . ?
C9 C14 C13 119.27(13) . . ?
C9 C14 C15 120.57(12) . . ?
C13 C14 C15 120.16(13) . . ?
N1 C15 C16 103.66(12) . . ?
N1 C15 C14 123.46(13) . . ?
C16 C15 C14 132.86(12) . . ?
N2 C16 C15 108.76(12) . . ?
N2 C16 C17 120.01(13) . . ?
C15 C16 C17 131.20(14) . . ?
O1 C17 C18 121.20(17) . . ?
O1 C17 C16 120.71(16) . . ?
C18 C17 C16 118.08(16) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

_refine_diff_density_max         0.213
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.027

_shelxl_version_number           2014-3



