# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1521357'
_audit_update_record             
;
2016-12-07 deposited with the CCDC.
2017-03-02 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         'C18 H13 N3 O2'
_chemical_formula_sum            'C18 H13 N3 O2'
_chemical_formula_weight         303.31

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'
O O 0.0492 0.0322 '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                   18.832(3)
_cell_length_b                   3.8846(6)
_cell_length_c                   20.977(3)
_cell_angle_alpha                90
_cell_angle_beta                 115.297(17)
_cell_angle_gamma                90
_cell_volume                     1387.4(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    130(1)
_cell_measurement_reflns_used    1315
_cell_measurement_theta_min      4.1460
_cell_measurement_theta_max      74.6240

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.452
_exptl_crystal_F_000             632
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.794
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.74927
_exptl_absorpt_correction_T_max  0.76233
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Spherical absorption correction
 using equivalent radius and absorption coefficient.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      130(1)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_detector_area_resol_mean 10.5357
_diffrn_measurement_method       '/w scan'
_diffrn_reflns_number            5060
_diffrn_reflns_av_unetI/netI     0.0629
_diffrn_reflns_av_R_equivalents  0.0658
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.645
_diffrn_reflns_theta_max         67.499
_diffrn_reflns_theta_full        67.499
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             2502
_reflns_number_gt                1839
_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 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
;
_computing_cell_refinement       
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
;
_computing_data_reduction        
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
;
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Mercury (MacRae et al., 2009)'
_computing_publication_material  'SHELXL (Sheldrick, 2015)'

_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)+(0.0926P)²+0.2500P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2502
_refine_ls_number_parameters     213
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0935
_refine_ls_R_factor_gt           0.0742
_refine_ls_wR_factor_ref         0.1972
_refine_ls_wR_factor_gt          0.1816
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.076
_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 0.43223(11) 0.2023(6) 0.41959(10) 0.0416(6) Uani 1 1 d . . . . .
C2 C 0.36091(17) 0.0546(9) 0.38103(16) 0.0397(7) Uani 1 1 d . . . . .
O2 O 0.31592(12) 0.0330(7) 0.40907(11) 0.0490(7) Uani 1 1 d . . . . .
C3 C 0.34434(17) -0.0622(9) 0.31044(15) 0.0386(7) Uani 1 1 d . . . . .
H3 H 0.2955 -0.1706 0.2831 0.046 Uiso 1 1 calc R U . . .
C4 C 0.39701(17) -0.0206(8) 0.28220(15) 0.0361(7) Uani 1 1 d . . . . .
C41 C 0.37684(18) -0.1349(9) 0.20792(15) 0.0419(7) Uani 1 1 d . . . . .
H41A H 0.3248 -0.2430 0.1879 0.063 Uiso 1 1 calc R U . . .
H41B H 0.4161 -0.3012 0.2082 0.063 Uiso 1 1 calc R U . . .
H41C H 0.3765 0.0650 0.1793 0.063 Uiso 1 1 calc R U . . .
C5 C 0.47076(16) 0.1429(8) 0.32343(15) 0.0342(7) Uani 1 1 d . . . . .
C6 C 0.53168(17) 0.2036(8) 0.30215(15) 0.0377(7) Uani 1 1 d . . . . .
H6 H 0.5245 0.1289 0.2567 0.045 Uiso 1 1 calc R U . . .
C7 C 0.60021(17) 0.3646(9) 0.34415(15) 0.0390(7) Uani 1 1 d . . . . .
H7 H 0.6394 0.4000 0.3276 0.047 Uiso 1 1 calc R U . . .
C8 C 0.61326(15) 0.4795(8) 0.41247(15) 0.0356(7) Uani 1 1 d . . . . .
C9 C 0.55468(16) 0.4128(9) 0.43552(14) 0.0369(7) Uani 1 1 d . . . . .
H9 H 0.5623 0.4806 0.4815 0.044 Uiso 1 1 calc R U . . .
C10 C 0.48720(16) 0.2519(9) 0.39239(15) 0.0362(7) Uani 1 1 d . . . . .
N11 N 0.67940(14) 0.6526(7) 0.45895(12) 0.0386(6) Uani 1 1 d . . . . .
H11 H 0.681(2) 0.737(10) 0.501(2) 0.054(10) Uiso 1 1 d . . . . .
C12 C 0.74251(17) 0.7715(9) 0.44822(15) 0.0375(7) Uani 1 1 d . . . . .
C121 C 0.80037(17) 0.9482(9) 0.50990(16) 0.0401(7) Uani 1 1 d . . . . .
N121 N 0.84550(16) 1.1014(9) 0.55647(15) 0.0497(7) Uani 1 1 d . . . . .
N13 N 0.74862(15) 0.7401(8) 0.38976(13) 0.0429(7) Uani 1 1 d . . . . .
C14 C 0.81785(17) 0.8461(9) 0.38318(15) 0.0376(7) Uani 1 1 d . . . . .
C15 C 0.80707(18) 1.0356(9) 0.32331(15) 0.0418(8) Uani 1 1 d . . . . .
H15 H 0.7558 1.1037 0.2909 0.050 Uiso 1 1 calc R U . . .
C16 C 0.87212(19) 1.1244(10) 0.31144(16) 0.0456(8) Uani 1 1 d . . . . .
H16 H 0.8652 1.2561 0.2710 0.055 Uiso 1 1 calc R U . . .
C17 C 0.94664(18) 1.0223(10) 0.35798(17) 0.0459(8) Uani 1 1 d . . . . .
H17 H 0.9907 1.0811 0.3493 0.055 Uiso 1 1 calc R U . . .
C18 C 0.95685(18) 0.8352(10) 0.41698(17) 0.0461(8) Uani 1 1 d . . . . .
H18 H 1.0081 0.7660 0.4492 0.055 Uiso 1 1 calc R U . . .
C19 C 0.89211(17) 0.7464(9) 0.42972(16) 0.0421(8) Uani 1 1 d . . . . .
H19 H 0.8994 0.6172 0.4705 0.050 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 C2 1.363(4) . ?
O1 C10 1.393(3) . ?
C2 O2 1.223(3) . ?
C2 C3 1.449(4) . ?
C3 C4 1.365(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.433(4) . ?
C4 C41 1.504(4) . ?
C41 H41A 0.9800 . ?
C41 H41B 0.9800 . ?
C41 H41C 0.9800 . ?
C5 C10 1.409(4) . ?
C5 C6 1.417(4) . ?
C6 C7 1.364(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.419(4) . ?
C7 H7 0.9500 . ?
C8 N11 1.384(4) . ?
C8 C9 1.405(4) . ?
C9 C10 1.357(4) . ?
C9 H9 0.9500 . ?
N11 C12 1.380(4) . ?
N11 H11 0.93(4) . ?
C12 N13 1.286(4) . ?
C12 C121 1.459(5) . ?
C121 N121 1.149(4) . ?
N13 C14 1.429(4) . ?
C14 C19 1.375(4) . ?
C14 C15 1.394(4) . ?
C15 C16 1.394(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.382(5) . ?
C16 H16 0.9500 . ?
C17 C18 1.376(5) . ?
C17 H17 0.9500 . ?
C18 C19 1.398(4) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?

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
C2 O1 C10 122.1(2) . . ?
O2 C2 O1 116.9(3) . . ?
O2 C2 C3 125.4(3) . . ?
O1 C2 C3 117.7(2) . . ?
C4 C3 C2 121.8(3) . . ?
C4 C3 H3 119.1 . . ?
C2 C3 H3 119.1 . . ?
C3 C4 C5 119.1(3) . . ?
C3 C4 C41 120.4(3) . . ?
C5 C4 C41 120.4(2) . . ?
C4 C41 H41A 109.5 . . ?
C4 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
C4 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C10 C5 C6 114.9(3) . . ?
C10 C5 C4 119.0(2) . . ?
C6 C5 C4 126.1(3) . . ?
C7 C6 C5 122.9(3) . . ?
C7 C6 H6 118.6 . . ?
C5 C6 H6 118.6 . . ?
C6 C7 C8 120.3(2) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
N11 C8 C9 116.7(2) . . ?
N11 C8 C7 125.4(2) . . ?
C9 C8 C7 117.9(3) . . ?
C10 C9 C8 120.3(3) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C9 C10 O1 116.0(2) . . ?
C9 C10 C5 123.7(2) . . ?
O1 C10 C5 120.2(3) . . ?
C12 N11 C8 128.8(2) . . ?
C12 N11 H11 111(2) . . ?
C8 N11 H11 120(2) . . ?
N13 C12 N11 123.9(3) . . ?
N13 C12 C121 123.6(3) . . ?
N11 C12 C121 112.4(2) . . ?
N121 C121 C12 176.7(4) . . ?
C12 N13 C14 121.5(3) . . ?
C19 C14 C15 120.0(3) . . ?
C19 C14 N13 122.9(3) . . ?
C15 C14 N13 116.8(3) . . ?
C16 C15 C14 119.4(3) . . ?
C16 C15 H15 120.3 . . ?
C14 C15 H15 120.3 . . ?
C17 C16 C15 120.5(3) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C18 C17 C16 119.8(3) . . ?
C18 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
C17 C18 C19 120.3(3) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
C14 C19 C18 120.0(3) . . ?
C14 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?

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
C7 H7 N13 0.95 2.32 2.927(4) 121.1 .
C9 H9 O1 0.95 2.38 3.301(3) 164.0 3_666
N11 H11 O2 0.93(4) 2.06(4) 2.993(3) 175(3) 3_666

_refine_diff_density_max         0.306
_refine_diff_density_min         -0.425
_refine_diff_density_rms         0.079

