# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_n1
_database_code_depnum_ccdc_archive 'CCDC 2005782'
loop_
_audit_author_name
_audit_author_address
'Jian-Bin Lin'
;Memorial University of Newfoundland
Canada
;
_audit_update_record             
;
2020-05-26 deposited with the CCDC.	2020-09-04 downloaded from the CCDC.
;
_audit_creation_date             2020-02-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H14 N2 O'
_chemical_formula_sum            'C19 H14 N2 O'
_chemical_formula_weight         286.32
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         C19H14N2O
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   8.8495(2)
_cell_length_b                   5.05830(10)
_cell_length_c                   16.2521(3)
_cell_angle_alpha                90
_cell_angle_beta                 102.686(2)
_cell_angle_gamma                90
_cell_volume                     709.74(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5311
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.7060
_cell_measurement_theta_min      5.5720
_shelx_estimated_absorpt_T_max   0.974
_shelx_estimated_absorpt_T_min   0.912
_exptl_absorpt_coefficient_mu    0.667
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57412
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.68a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0556
_diffrn_reflns_av_unetI/netI     0.0420
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            13880
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.368
_diffrn_reflns_theta_min         2.787
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -16.00  28.00   0.50    3.87    --  -47.82  19.00 -30.00   88
  2  ω    -43.00 -14.00   0.50   18.00    --  -86.25  45.00 -30.00   58
  3  ω    -83.00  -5.00   0.50    3.87    --  -47.82 114.00 124.00  156
  4  ω     27.00  90.00   0.50    3.87    --   47.82-114.00  32.00  126
  5  ω     59.00 121.00   0.50    3.87    --   47.82-175.00-105.00  124
  6  ω     59.00 148.00   0.50   18.00    --  107.75-175.00-105.00  178
  7  ω     35.00 108.00   0.50   18.00    --  107.75-114.00  32.00  146
  8  ω     35.00 106.00   0.50   18.00    --  107.75-101.00  42.08  142
  9  ω     35.00  79.00   0.50   18.00    --  107.75 -61.00  90.00   88
 10  ω     35.00 106.00   0.50   18.00    --  107.75 -94.00  60.00  142
 11  ω     35.00 106.00   0.50   18.00    --  107.75 -94.00   0.00  142
 12  ω     35.00 106.00   0.50   18.00    --  107.75 -94.00-150.00  142
 13  ω     35.00 106.00   0.50   18.00    --  107.75 -94.00 -90.00  142
 14  ω     35.00 108.00   0.50   18.00    --  107.75-109.00 -51.96  146
 15  ω     35.00 106.00   0.50   18.00    --  107.75 -94.00-120.00  142
 16  ω     94.00 178.00   0.50   18.00    --  107.75  15.00 -60.00  168
 17  ω     95.00 178.00   0.50   18.00    --  107.75 125.00-150.00  166
 18  ω     95.00 178.00   0.50   18.00    --  107.75  30.00   0.00  166
 19  ω    102.00 178.00   0.50   18.00    --  107.75 114.00 124.00  152
 20  ω     95.00 178.00   0.50   18.00    --  107.75  45.00  60.00  166
 21  ω     95.00 178.00   0.50   18.00    --  107.75 125.00 -30.00  166
 22  ω     95.00 178.00   0.50   18.00    --  107.75  45.00-120.00  166
 23  ω     95.00 178.00   0.50   18.00    --  107.75 125.00 -60.00  166
 24  ω     91.00 178.00   0.50   18.00    --  107.75  61.00  30.00  174
 25  ω     95.00 178.00   0.50   18.00    --  107.75  45.00 150.00  166
 26  ω     85.00 178.00   0.50   18.00    --  107.75  77.00  90.00  186
 27  ω     91.00 178.00   0.50   18.00    --  107.75  61.00 -60.00  174
 28  ω     85.00 178.00   0.50   18.00    --  107.75  77.00-180.00  186
 29  ω     91.00 178.00   0.50   18.00    --  107.75  61.00-150.00  174
 30  ω     64.00 147.00   0.50   18.00    --  107.75 175.00 -97.00  166
 31  ω    -26.00  30.00   0.50    3.87    --   47.82 -19.00-120.00  112
 32  ω     35.00 112.00   0.50   18.00    --  107.75-125.00 150.00  154
 33  ω     35.00 107.00   0.50   18.00    --  107.75-104.00 166.68  144
 34  ω   -119.00 -43.00   0.50    3.87    --  -47.82-175.00-105.00  152
 35  ω   -119.00 -25.00   0.50    3.87    --  -47.82 -77.00 -30.00  188
 36  ω   -119.00 -81.50   0.50    3.87    --  -47.82 -77.00  60.00   75
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1677205000
_diffrn_orient_matrix_UB_12      -0.0599551000
_diffrn_orient_matrix_UB_13      -0.0065967000
_diffrn_orient_matrix_UB_21      -0.0421290000
_diffrn_orient_matrix_UB_22      -0.2938421000
_diffrn_orient_matrix_UB_23      -0.0159387000
_diffrn_orient_matrix_UB_31      -0.0443233000
_diffrn_orient_matrix_UB_32      0.0531749000
_diffrn_orient_matrix_UB_33      -0.0955635000
_diffrn_oxdiff_digest_frames     
;
01e4108e1641e6aad062c5ab9057ce0f6c0002677d4
;
_diffrn_oxdiff_digest_hkl        
;
018bcf4812d030638a775b5a87c7e08df369bb
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.763
_reflns_Friedel_fraction_full    0.987
_reflns_Friedel_fraction_max     0.959
_reflns_number_gt                2823
_reflns_number_total             2943
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 
;
 Flack x determined using 1163 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.26(14)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         2943
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0417
_refine_ls_R_factor_gt           0.0396
_refine_ls_restrained_S_all      1.095
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0305P)²+0.2788P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0962
_refine_ls_wR_factor_ref         0.0972
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C15(H15), C16(H16),
 C17(H17), C18(H18), C19(H19)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.5437(2) 0.9822(4) 0.29780(11) 0.0264(4) Uani 1 1 d . . . . .
N1 N 0.5891(3) 0.7064(6) 0.09291(15) 0.0381(6) Uani 1 1 d . . . . .
N2 N 0.4780(2) 0.5547(4) 0.27446(13) 0.0214(4) Uani 1 1 d . . . . .
H2 H 0.496(4) 0.388(8) 0.288(2) 0.034(9) Uiso 1 1 d . . . . .
C1 C 0.2749(3) 0.4040(5) 0.15328(16) 0.0231(5) Uani 1 1 d . . . . .
C2 C 0.1376(3) 0.3833(5) 0.18622(16) 0.0240(5) Uani 1 1 d . . . . .
C3 C 0.1044(3) 0.5535(5) 0.24949(16) 0.0263(5) Uani 1 1 d . . . . .
H3 H 0.176773 0.686538 0.273169 0.032 Uiso 1 1 calc R . . . .
C4 C -0.0305(3) 0.5280(6) 0.27669(18) 0.0319(6) Uani 1 1 d . . . . .
H4 H -0.052233 0.647631 0.317669 0.038 Uiso 1 1 calc R . . . .
C5 C -0.1376(3) 0.3279(6) 0.2450(2) 0.0358(7) Uani 1 1 d . . . . .
H5 H -0.228929 0.308258 0.266088 0.043 Uiso 1 1 calc R . . . .
C6 C -0.1097(3) 0.1617(6) 0.1838(2) 0.0362(7) Uani 1 1 d . . . . .
H6 H -0.183039 0.028045 0.162001 0.043 Uiso 1 1 calc R . . . .
C7 C 0.0271(3) 0.1851(5) 0.15199(17) 0.0271(6) Uani 1 1 d . . . . .
C8 C 0.0546(3) 0.0192(6) 0.08656(17) 0.0325(6) Uani 1 1 d . . . . .
H8 H -0.018358 -0.114550 0.064312 0.039 Uiso 1 1 calc R . . . .
C9 C 0.1841(3) 0.0486(5) 0.05514(17) 0.0316(6) Uani 1 1 d . . . . .
H9 H 0.199669 -0.061056 0.010270 0.038 Uiso 1 1 calc R . . . .
C10 C 0.2953(3) 0.2423(5) 0.08930(16) 0.0260(5) Uani 1 1 d . . . . .
H10 H 0.385902 0.260332 0.067397 0.031 Uiso 1 1 calc R . . . .
C11 C 0.3920(3) 0.6159(5) 0.18906(15) 0.0226(5) Uani 1 1 d . . . . .
H11 H 0.333684 0.783683 0.191981 0.027 Uiso 1 1 calc R . . . .
C12 C 0.5030(3) 0.6656(6) 0.13434(16) 0.0276(6) Uani 1 1 d . . . . .
C13 C 0.5533(3) 0.7509(5) 0.32272(15) 0.0214(5) Uani 1 1 d . . . . .
C14 C 0.6482(3) 0.6800(5) 0.40791(15) 0.0212(5) Uani 1 1 d . . . . .
C15 C 0.7730(3) 0.8420(5) 0.44203(16) 0.0252(5) Uani 1 1 d . . . . .
H15 H 0.798255 0.986260 0.410124 0.030 Uiso 1 1 calc R . . . .
C16 C 0.8608(3) 0.7943(5) 0.52230(16) 0.0265(5) Uani 1 1 d . . . . .
H16 H 0.946873 0.904267 0.545050 0.032 Uiso 1 1 calc R . . . .
C17 C 0.8229(3) 0.5857(5) 0.56944(16) 0.0253(5) Uani 1 1 d . . . . .
H17 H 0.881871 0.554893 0.624912 0.030 Uiso 1 1 calc R . . . .
C18 C 0.6993(3) 0.4225(5) 0.53569(16) 0.0246(5) Uani 1 1 d . . . . .
H18 H 0.674162 0.279137 0.567995 0.029 Uiso 1 1 calc R . . . .
C19 C 0.6118(3) 0.4672(5) 0.45473(15) 0.0227(5) Uani 1 1 d . . . . .
H19 H 0.527715 0.353643 0.431443 0.027 Uiso 1 1 calc R . . . .


_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 C13 1.235(3) . ?
N1 C12 1.141(4) . ?
N2 H2 0.88(4) . ?
N2 C11 1.462(3) . ?
N2 C13 1.347(3) . ?
C1 C2 1.435(4) . ?
C1 C10 1.366(4) . ?
C1 C11 1.516(3) . ?
C2 C3 1.420(4) . ?
C2 C7 1.425(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.367(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.404(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.367(5) . ?
C6 H6 0.9500 . ?
C6 C7 1.421(4) . ?
C7 C8 1.417(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.361(5) . ?
C9 H9 0.9500 . ?
C9 C10 1.413(4) . ?
C10 H10 0.9500 . ?
C11 H11 1.0000 . ?
C11 C12 1.484(4) . ?
C13 C14 1.497(3) . ?
C14 C15 1.389(4) . ?
C14 C19 1.396(4) . ?
C15 H15 0.9500 . ?
C15 C16 1.385(4) . ?
C16 H16 0.9500 . ?
C16 C17 1.388(4) . ?
C17 H17 0.9500 . ?
C17 C18 1.384(4) . ?
C18 H18 0.9500 . ?
C18 C19 1.391(4) . ?
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
C11 N2 H2 118(2) . . ?
C13 N2 H2 122(2) . . ?
C13 N2 C11 119.0(2) . . ?
C2 C1 C11 118.2(2) . . ?
C10 C1 C2 120.3(2) . . ?
C10 C1 C11 121.4(2) . . ?
C3 C2 C1 123.5(2) . . ?
C3 C2 C7 118.4(2) . . ?
C7 C2 C1 118.1(2) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 C2 120.7(3) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 H4 119.5 . . ?
C3 C4 C5 121.1(3) . . ?
C5 C4 H4 119.5 . . ?
C4 C5 H5 120.2 . . ?
C6 C5 C4 119.7(3) . . ?
C6 C5 H5 120.2 . . ?
C5 C6 H6 119.4 . . ?
C5 C6 C7 121.2(3) . . ?
C7 C6 H6 119.4 . . ?
C6 C7 C2 118.9(3) . . ?
C8 C7 C2 119.5(3) . . ?
C8 C7 C6 121.6(3) . . ?
C7 C8 H8 119.5 . . ?
C9 C8 C7 120.9(2) . . ?
C9 C8 H8 119.5 . . ?
C8 C9 H9 120.0 . . ?
C8 C9 C10 120.0(3) . . ?
C10 C9 H9 120.0 . . ?
C1 C10 C9 121.1(3) . . ?
C1 C10 H10 119.4 . . ?
C9 C10 H10 119.4 . . ?
N2 C11 C1 112.6(2) . . ?
N2 C11 H11 107.5 . . ?
N2 C11 C12 109.3(2) . . ?
C1 C11 H11 107.5 . . ?
C12 C11 C1 112.1(2) . . ?
C12 C11 H11 107.5 . . ?
N1 C12 C11 179.2(3) . . ?
O1 C13 N2 121.2(2) . . ?
O1 C13 C14 121.0(2) . . ?
N2 C13 C14 117.8(2) . . ?
C15 C14 C13 117.6(2) . . ?
C15 C14 C19 119.7(2) . . ?
C19 C14 C13 122.6(2) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 C14 120.4(2) . . ?
C16 C15 H15 119.8 . . ?
C15 C16 H16 120.0 . . ?
C15 C16 C17 119.9(2) . . ?
C17 C16 H16 120.0 . . ?
C16 C17 H17 120.0 . . ?
C18 C17 C16 120.0(2) . . ?
C18 C17 H17 120.0 . . ?
C17 C18 H18 119.8 . . ?
C17 C18 C19 120.4(2) . . ?
C19 C18 H18 119.8 . . ?
C14 C19 H19 120.2 . . ?
C18 C19 C14 119.6(2) . . ?
C18 C19 H19 120.2 . . ?

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
_geom_hbond_publ_flag
N2 H2 O1 0.88(4) 2.09(4) 2.961(3) 169(3) 1_545 yes

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
O1 C13 C14 C15 -27.3(4) . . . . ?
O1 C13 C14 C19 149.8(2) . . . . ?
N2 C13 C14 C15 153.1(2) . . . . ?
N2 C13 C14 C19 -29.7(3) . . . . ?
C1 C2 C3 C4 178.2(2) . . . . ?
C1 C2 C7 C6 -179.9(2) . . . . ?
C1 C2 C7 C8 -0.8(3) . . . . ?
C2 C1 C10 C9 -1.1(4) . . . . ?
C2 C1 C11 N2 72.5(3) . . . . ?
C2 C1 C11 C12 -163.8(2) . . . . ?
C2 C3 C4 C5 2.1(4) . . . . ?
C2 C7 C8 C9 -0.9(4) . . . . ?
C3 C2 C7 C6 -1.5(3) . . . . ?
C3 C2 C7 C8 177.6(2) . . . . ?
C3 C4 C5 C6 -2.5(4) . . . . ?
C4 C5 C6 C7 0.8(4) . . . . ?
C5 C6 C7 C2 1.1(4) . . . . ?
C5 C6 C7 C8 -177.9(3) . . . . ?
C6 C7 C8 C9 178.2(3) . . . . ?
C7 C2 C3 C4 -0.2(4) . . . . ?
C7 C8 C9 C10 1.7(4) . . . . ?
C8 C9 C10 C1 -0.6(4) . . . . ?
C10 C1 C2 C3 -176.6(2) . . . . ?
C10 C1 C2 C7 1.8(3) . . . . ?
C10 C1 C11 N2 -109.8(3) . . . . ?
C10 C1 C11 C12 13.9(3) . . . . ?
C11 N2 C13 O1 4.0(4) . . . . ?
C11 N2 C13 C14 -176.4(2) . . . . ?
C11 C1 C2 C3 1.1(4) . . . . ?
C11 C1 C2 C7 179.5(2) . . . . ?
C11 C1 C10 C9 -178.8(2) . . . . ?
C13 N2 C11 C1 -161.8(2) . . . . ?
C13 N2 C11 C12 72.9(3) . . . . ?
C13 C14 C15 C16 176.9(2) . . . . ?
C13 C14 C19 C18 -176.0(2) . . . . ?
C14 C15 C16 C17 -0.8(4) . . . . ?
C15 C14 C19 C18 1.1(4) . . . . ?
C15 C16 C17 C18 1.2(4) . . . . ?
C16 C17 C18 C19 -0.4(4) . . . . ?
C17 C18 C19 C14 -0.7(4) . . . . ?
C19 C14 C15 C16 -0.4(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.127
_oxdiff_exptl_absorpt_empirical_full_min 0.615
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Hexane and Chloroform'
####################################################################### 
# 
# 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_n2
_database_code_depnum_ccdc_archive 'CCDC 2005785'
loop_
_audit_author_name
_audit_author_address
'Jian-Bin Lin'
;Memorial University of Newfoundland
Canada
;
_audit_update_record             
;
2020-05-26 deposited with the CCDC.	2020-09-04 downloaded from the CCDC.
;
_audit_creation_date             2020-02-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H13 N3 O3'
_chemical_formula_sum            'C19 H13 N3 O3'
_chemical_formula_weight         331.32
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         C19H14N2O
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   4.98087(4)
_cell_length_b                   14.03570(14)
_cell_length_c                   11.32877(11)
_cell_angle_alpha                90
_cell_angle_beta                 94.4463(8)
_cell_angle_gamma                90
_cell_volume                     789.610(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    13528
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.9070
_cell_measurement_theta_min      3.8670
_shelx_estimated_absorpt_T_max   0.954
_shelx_estimated_absorpt_T_min   0.845
_exptl_absorpt_coefficient_mu    0.797
_exptl_absorpt_correction_T_max  0.95155
_exptl_absorpt_correction_T_min  0.95155
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.68a (Rigaku Oxford Diffraction, 2019)
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   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             344
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-2 1 1 0.1160
2 -1 -1 0.0871
0 -1 0 0.0375
1 -1 -2 0.0699
-1 0 2 0.1041
0 0 1 0.0346
0 0 -1 0.0253
-1 -2 -1 0.1013
1 2 1 0.0920
3 5 -2 0.0891
0 6 -6 0.0224
0 8 -4 0.0184
0 8 4 0.0373
0 -6 6 0.0422
0 -8 -4 0.0261

_exptl_crystal_size_max          0.219
_exptl_crystal_size_mid          0.071
_exptl_crystal_size_min          0.06
_exptl_crystal_size_rad          0.053
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-1.9995 1.0067 1.0040 -0.0446 0.4674 -0.4265
1.9995 -1.0067 -1.0040 0.0446 -0.4674 0.4265
-0.0004 -0.9998 -0.0005 0.0752 -0.0632 -0.0489
0.9989 -1.0027 -2.0022 0.2058 -0.1828 0.3063
-0.9993 0.0028 2.0017 -0.1306 0.1196 -0.3552
0.0004 -0.0004 1.0000 -0.0972 -0.0550 -0.0783
-0.0004 0.0004 -1.0000 0.0972 0.0550 0.0783
-1.0013 -1.9956 -0.9992 0.3116 0.1581 -0.2179
1.0013 1.9956 0.9992 -0.3116 -0.1581 0.2179
2.6698 4.9624 -1.5594 -0.3931 -0.2124 0.8946
0.1333 5.9531 -5.5639 0.0852 0.6521 0.7534
0.1404 7.6703 -3.9672 -0.1996 0.6716 0.7135
-0.1696 7.8604 3.7147 -0.9410 0.3332 0.0591
-0.0865 -5.9508 5.5620 -0.0882 -0.6625 -0.7438
-0.0823 -7.5308 -4.1054 0.9704 -0.2331 -0.0624

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0548
_diffrn_reflns_av_unetI/netI     0.0295
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            19960
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.399
_diffrn_reflns_theta_min         3.914
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     33.00 119.00   0.50    0.05    --   47.82  57.00  90.00  172
  2  ω     91.00 178.00   0.50    0.30    --  107.75  61.00 120.00  174
  3  ω     95.00 178.00   0.50    0.30    --  107.75  45.00 150.00  166
  4  ω     85.00 178.00   0.50    0.30    --  107.75  77.00   0.00  186
  5  ω     95.00 178.00   0.50    0.30    --  107.75  30.00 120.00  166
  6  ω     95.00 178.00   0.50    0.30    --  107.75  45.00   0.00  166
  7  ω     95.00 178.00   0.50    0.30    --  107.75  30.00  90.00  166
  8  ω     88.00 178.00   0.50    0.30    --  107.75  70.00 -47.12  180
  9  ω     91.00 178.00   0.50    0.30    --  107.75  61.00 -90.00  174
 10  ω     95.00 178.00   0.50    0.30    --  107.75  45.00-150.00  166
 11  ω    -16.00  28.00   0.50    0.05    --  -47.82  19.00-150.00   88
 12  ω    -16.00  28.00   0.50    0.05    --  -47.82  19.00   0.00   88
 13  ω    -43.00 -14.00   0.50    0.30    --  -86.25  45.00  30.00   58
 14  ω   -113.00 -13.00   0.50    0.30    --  -86.25  87.00  18.00  200
 15  ω    -75.00  25.00   0.50    0.05    --  -47.82  87.00  18.00  200
 16  ω    101.00 178.00   0.50    0.30    --  107.75  87.00  18.00  154
 17  ω     95.00 178.00   0.50    0.30    --  107.75 125.00  60.00  166
 18  ω     95.00 178.00   0.50    0.30    --  107.75 125.00 120.00  166
 19  ω     35.00 112.00   0.50    0.30    --  107.75-125.00  60.00  154
 20  ω     35.00 112.00   0.50    0.30    --  107.75-125.00 -60.00  154
 21  ω     35.00 112.00   0.50    0.30    --  107.75-125.00 -90.00  154
 22  ω     35.00 106.00   0.50    0.30    --  107.75 -94.00-150.00  142
 23  ω     35.00 106.00   0.50    0.30    --  107.75 -94.00 -90.00  142
 24  ω     34.00  96.00   0.50    0.05    --   47.82-125.00-120.00  124
 25  ω    -21.00  75.00   0.50    0.05    --   47.82 -87.00 -98.00  192
 26  ω     35.00 135.00   0.50    0.30    --  107.75 -87.00 -98.00  200
 27  ω     35.00 106.00   0.50    0.30    --  107.75 -94.00 -30.00  142
 28  ω     35.00 106.00   0.50    0.30    --  107.75 -94.00 150.00  142
 29  ω     35.00 106.00   0.50    0.30    --  107.75 -94.00  90.00  142
 30  ω     35.00  79.00   0.50    0.30    --  107.75 -61.00 -30.00   88
 31  ω     35.00  79.00   0.50    0.30    --  107.75 -61.00 -90.00   88
 32  ω     35.00  79.00   0.50    0.30    --  107.75 -61.00-180.00   88
 33  ω     35.00  79.00   0.50    0.30    --  107.75 -61.00   0.00   88
 34  ω     35.00  79.00   0.50    0.30    --  107.75 -61.00  60.00   88
 35  ω     35.00  79.00   0.50    0.30    --  107.75 -61.00 120.00   88
 36  ω    -26.00  30.00   0.50    0.05    --   47.82 -19.00 -30.00  112
 37  ω   -119.00 -25.00   0.50    0.05    --  -47.82 -77.00 -60.00  188
 38  ω   -119.00 -25.00   0.50    0.05    --  -47.82 -77.00-180.00  188
 39  ω   -119.00 -25.00   0.50    0.05    --  -47.82 -77.00-150.00  188
 40  ω   -119.00 -25.00   0.50    0.05    --  -47.82 -77.00 -90.00  188
 41  ω   -119.00 -25.00   0.50    0.05    --  -47.82 -77.00 -30.00  188
 42  ω   -119.00 -25.00   0.50    0.05    --  -47.82 -77.00 120.00  188
 43  ω   -119.00 -25.00   0.50    0.05    --  -47.82 -77.00  90.00  188
 44  ω   -119.00 -25.00   0.50    0.05    --  -47.82 -77.00  30.00  188
 45  ω   -119.00 -33.00   0.50    0.05    --  -47.82 -57.00 -30.00  172
 46  ω   -159.00 -79.00   0.50    0.30    --  -86.25 -87.00 -98.00  160
 47  ω   -119.00 -73.00   0.50    0.05    --  -47.82-125.00 -30.00   92
 48  ω   -119.00 -73.00   0.50    0.05    --  -47.82-125.00  30.00   92
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0643672000
_diffrn_orient_matrix_UB_12      -0.0751427000
_diffrn_orient_matrix_UB_13      -0.0972535000
_diffrn_orient_matrix_UB_21      -0.2294073000
_diffrn_orient_matrix_UB_22      0.0633766000
_diffrn_orient_matrix_UB_23      -0.0548799000
_diffrn_orient_matrix_UB_31      0.1985214000
_diffrn_orient_matrix_UB_32      0.0488479000
_diffrn_orient_matrix_UB_33      -0.0783820000
_diffrn_oxdiff_digest_frames     
;
015033dbaa6088fb2d60ac4f111bbb2deb00121efc1
;
_diffrn_oxdiff_digest_hkl        
;
01c51d3a9adec9d075c8ac12d259991d18a712
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.900
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.973
_reflns_number_gt                3242
_reflns_number_total             3300
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.166
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 
;
 Flack x determined using 1487 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         3300
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0314
_refine_ls_R_factor_gt           0.0309
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0405P)²+0.1253P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0785
_refine_ls_wR_factor_ref         0.0791
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C15(H15), C16(H16),
 C18(H18), C19(H19)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.2268(3) 0.57250(11) 0.72654(13) 0.0248(3) Uani 1 1 d . . . . .
O2 O 0.9804(4) 0.21677(16) 1.0699(2) 0.0628(7) Uani 1 1 d . . . . .
O3 O 0.6329(5) 0.14849(12) 0.98866(17) 0.0483(5) Uani 1 1 d . . . . .
N1 N 0.5510(5) 0.85080(14) 0.81839(18) 0.0384(5) Uani 1 1 d . . . . .
N2 N 0.6593(3) 0.62199(12) 0.73102(14) 0.0200(3) Uani 1 1 d . . . . .
N3 N 0.7757(4) 0.21794(13) 1.00554(16) 0.0296(4) Uani 1 1 d . . . . .
C1 C 0.7710(4) 0.73306(14) 0.57205(17) 0.0200(4) Uani 1 1 d . . . . .
C2 C 0.7686(4) 0.67195(14) 0.47117(17) 0.0202(4) Uani 1 1 d . . . . .
C3 C 0.5883(4) 0.59413(14) 0.45293(19) 0.0251(4) Uani 1 1 d . . . . .
H3 H 0.464313 0.580507 0.510296 0.030 Uiso 1 1 calc R . . . .
C4 C 0.5905(5) 0.53836(16) 0.3538(2) 0.0305(5) Uani 1 1 d . . . . .
H4 H 0.465094 0.487592 0.342236 0.037 Uiso 1 1 calc R . . . .
C5 C 0.7765(5) 0.55542(17) 0.2688(2) 0.0335(5) Uani 1 1 d . . . . .
H5 H 0.779773 0.515218 0.201448 0.040 Uiso 1 1 calc R . . . .
C6 C 0.9522(4) 0.62982(17) 0.28333(18) 0.0300(5) Uani 1 1 d . . . . .
H6 H 1.078209 0.640706 0.226004 0.036 Uiso 1 1 calc R . . . .
C7 C 0.9496(4) 0.69136(14) 0.38301(18) 0.0234(4) Uani 1 1 d . . . . .
C8 C 1.1189(4) 0.77207(16) 0.39545(18) 0.0267(4) Uani 1 1 d . . . . .
H8 H 1.240695 0.784972 0.336961 0.032 Uiso 1 1 calc R . . . .
C9 C 1.1102(4) 0.83191(16) 0.4903(2) 0.0269(4) Uani 1 1 d . . . . .
H9 H 1.220652 0.887152 0.495943 0.032 Uiso 1 1 calc R . . . .
C10 C 0.9365(4) 0.81143(14) 0.58003(18) 0.0223(4) Uani 1 1 d . . . . .
H10 H 0.934274 0.852419 0.646676 0.027 Uiso 1 1 calc R . . . .
C11 C 0.5841(4) 0.70990(15) 0.66815(17) 0.0211(4) Uani 1 1 d . . . . .
H11 H 0.399795 0.700302 0.628390 0.025 Uiso 1 1 calc R . . . .
C12 C 0.5671(4) 0.78924(15) 0.75322(18) 0.0266(4) Uani 1 1 d . . . . .
C13 C 0.4666(4) 0.56000(13) 0.75741(16) 0.0187(4) Uani 1 1 d . . . . .
C14 C 0.5587(4) 0.47190(14) 0.82381(16) 0.0189(4) Uani 1 1 d . . . . .
C15 C 0.7874(4) 0.47039(14) 0.90356(17) 0.0212(4) Uani 1 1 d . . . . .
H15 H 0.893385 0.526260 0.916227 0.025 Uiso 1 1 calc R . . . .
C16 C 0.8594(4) 0.38729(15) 0.96412(18) 0.0235(4) Uani 1 1 d . . . . .
H16 H 1.013442 0.385392 1.019018 0.028 Uiso 1 1 calc R . . . .
C17 C 0.7008(4) 0.30693(14) 0.94256(18) 0.0225(4) Uani 1 1 d . . . . .
C18 C 0.4726(4) 0.30643(15) 0.86482(18) 0.0243(4) Uani 1 1 d . . . . .
H18 H 0.366922 0.250437 0.852656 0.029 Uiso 1 1 calc R . . . .
C19 C 0.4028(4) 0.39016(15) 0.80519(17) 0.0226(4) Uani 1 1 d . . . . .
H19 H 0.247145 0.391769 0.751147 0.027 Uiso 1 1 calc R . . . .
H2 H 0.837(6) 0.609(2) 0.745(3) 0.038(7) Uiso 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
O1 C13 1.231(2) . ?
O2 N3 1.206(3) . ?
O3 N3 1.213(3) . ?
N1 C12 1.143(3) . ?
N2 C11 1.459(2) . ?
N2 C13 1.346(2) . ?
N2 H2 0.91(3) . ?
N3 C17 1.472(3) . ?
C1 C2 1.428(3) . ?
C1 C10 1.373(3) . ?
C1 C11 1.521(3) . ?
C2 C3 1.419(3) . ?
C2 C7 1.423(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.370(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.408(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.364(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.423(3) . ?
C7 C8 1.413(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.367(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.414(3) . ?
C10 H10 0.9500 . ?
C11 H11 1.0000 . ?
C11 C12 1.479(3) . ?
C13 C14 1.500(3) . ?
C14 C15 1.398(3) . ?
C14 C19 1.392(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.386(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.388(3) . ?
C17 C18 1.383(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.386(3) . ?
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
C11 N2 H2 117(2) . . ?
C13 N2 C11 119.65(16) . . ?
C13 N2 H2 123(2) . . ?
O2 N3 O3 122.8(2) . . ?
O2 N3 C17 118.37(19) . . ?
O3 N3 C17 118.80(18) . . ?
C2 C1 C11 118.47(17) . . ?
C10 C1 C2 120.10(17) . . ?
C10 C1 C11 121.43(18) . . ?
C3 C2 C1 123.01(18) . . ?
C3 C2 C7 118.26(18) . . ?
C7 C2 C1 118.71(17) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 C2 120.9(2) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 H4 119.6 . . ?
C3 C4 C5 120.8(2) . . ?
C5 C4 H4 119.6 . . ?
C4 C5 H5 120.1 . . ?
C6 C5 C4 119.8(2) . . ?
C6 C5 H5 120.1 . . ?
C5 C6 H6 119.5 . . ?
C5 C6 C7 121.0(2) . . ?
C7 C6 H6 119.5 . . ?
C6 C7 C2 119.10(19) . . ?
C8 C7 C2 119.29(18) . . ?
C8 C7 C6 121.60(19) . . ?
C7 C8 H8 119.5 . . ?
C9 C8 C7 121.07(18) . . ?
C9 C8 H8 119.5 . . ?
C8 C9 H9 120.1 . . ?
C8 C9 C10 119.89(19) . . ?
C10 C9 H9 120.1 . . ?
C1 C10 C9 120.86(19) . . ?
C1 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
N2 C11 C1 112.46(15) . . ?
N2 C11 H11 107.3 . . ?
N2 C11 C12 110.12(16) . . ?
C1 C11 H11 107.3 . . ?
C12 C11 C1 111.99(17) . . ?
C12 C11 H11 107.3 . . ?
N1 C12 C11 179.2(2) . . ?
O1 C13 N2 122.52(18) . . ?
O1 C13 C14 120.79(17) . . ?
N2 C13 C14 116.66(15) . . ?
C15 C14 C13 122.57(17) . . ?
C19 C14 C13 117.26(16) . . ?
C19 C14 C15 120.15(18) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 C14 119.94(18) . . ?
C16 C15 H15 120.0 . . ?
C15 C16 H16 120.8 . . ?
C15 C16 C17 118.36(17) . . ?
C17 C16 H16 120.8 . . ?
C16 C17 N3 118.99(18) . . ?
C18 C17 N3 118.00(18) . . ?
C18 C17 C16 123.00(18) . . ?
C17 C18 H18 121.0 . . ?
C17 C18 C19 117.96(19) . . ?
C19 C18 H18 121.0 . . ?
C14 C19 H19 119.7 . . ?
C18 C19 C14 120.58(18) . . ?
C18 C19 H19 119.7 . . ?

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
_geom_hbond_publ_flag
N2 H2 O1 0.91(3) 2.03(3) 2.915(2) 164(3) 1_655 yes

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
O1 C13 C14 C15 -151.19(18) . . . . ?
O1 C13 C14 C19 27.5(3) . . . . ?
O2 N3 C17 C16 -3.4(3) . . . . ?
O2 N3 C17 C18 177.1(2) . . . . ?
O3 N3 C17 C16 178.20(19) . . . . ?
O3 N3 C17 C18 -1.3(3) . . . . ?
N2 C13 C14 C15 30.7(3) . . . . ?
N2 C13 C14 C19 -150.64(17) . . . . ?
N3 C17 C18 C19 -179.74(17) . . . . ?
C1 C2 C3 C4 178.94(19) . . . . ?
C1 C2 C7 C6 178.81(18) . . . . ?
C1 C2 C7 C8 -2.3(3) . . . . ?
C2 C1 C10 C9 -1.2(3) . . . . ?
C2 C1 C11 N2 67.3(2) . . . . ?
C2 C1 C11 C12 -168.05(16) . . . . ?
C2 C3 C4 C5 1.6(3) . . . . ?
C2 C7 C8 C9 -0.4(3) . . . . ?
C3 C2 C7 C6 -3.0(3) . . . . ?
C3 C2 C7 C8 175.95(18) . . . . ?
C3 C4 C5 C6 -1.8(3) . . . . ?
C4 C5 C6 C7 -0.5(3) . . . . ?
C5 C6 C7 C2 2.9(3) . . . . ?
C5 C6 C7 C8 -176.04(19) . . . . ?
C6 C7 C8 C9 178.50(19) . . . . ?
C7 C2 C3 C4 0.8(3) . . . . ?
C7 C8 C9 C10 2.3(3) . . . . ?
C8 C9 C10 C1 -1.5(3) . . . . ?
C10 C1 C2 C3 -175.05(18) . . . . ?
C10 C1 C2 C7 3.1(3) . . . . ?
C10 C1 C11 N2 -113.6(2) . . . . ?
C10 C1 C11 C12 11.0(2) . . . . ?
C11 N2 C13 O1 2.9(3) . . . . ?
C11 N2 C13 C14 -179.07(16) . . . . ?
C11 C1 C2 C3 4.0(3) . . . . ?
C11 C1 C2 C7 -177.85(16) . . . . ?
C11 C1 C10 C9 179.71(18) . . . . ?
C13 N2 C11 C1 -137.74(18) . . . . ?
C13 N2 C11 C12 96.6(2) . . . . ?
C13 C14 C15 C16 178.70(17) . . . . ?
C13 C14 C19 C18 -178.96(16) . . . . ?
C14 C15 C16 C17 0.5(3) . . . . ?
C15 C14 C19 C18 -0.3(3) . . . . ?
C15 C16 C17 N3 179.55(17) . . . . ?
C15 C16 C17 C18 -0.9(3) . . . . ?
C16 C17 C18 C19 0.8(3) . . . . ?
C17 C18 C19 C14 -0.1(3) . . . . ?
C19 C14 C15 C16 0.1(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.311
_oxdiff_exptl_absorpt_empirical_full_min 0.836
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Hexane and Chloroform'
####################################################################### 
# 
# 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_n3
_database_code_depnum_ccdc_archive 'CCDC 2005786'
loop_
_audit_author_name
_audit_author_address
'Jian-Bin Lin'
;Memorial University of Newfoundland
Canada
;
_audit_update_record             
;
2020-05-26 deposited with the CCDC.	2020-09-04 downloaded from the CCDC.
;
_audit_creation_date             2020-02-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H12 N4 O5'
_chemical_formula_sum            'C19 H12 N4 O5'
_chemical_formula_weight         376.33
_chemical_melting_point          ?
_chemical_oxdiff_formula         C19H13N4O2
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   8.3646(2)
_cell_length_b                   22.9273(6)
_cell_length_c                   9.4978(2)
_cell_angle_alpha                90
_cell_angle_beta                 110.706(3)
_cell_angle_gamma                90
_cell_volume                     1703.81(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5183
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.7380
_cell_measurement_theta_min      5.9600
_shelx_estimated_absorpt_T_max   0.947
_shelx_estimated_absorpt_T_min   0.852
_exptl_absorpt_coefficient_mu    0.922
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54251
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.68a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.467
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0532
_diffrn_reflns_av_unetI/netI     0.0471
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            14535
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.273
_diffrn_reflns_theta_min         3.856
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -16.00  28.00   0.50    4.57    --  -47.82  19.00 -60.00   88
  2  ω    -16.00  28.00   0.50    4.57    --  -47.82  19.00-120.00   88
  3  ω    -16.00  10.00   0.50    4.57    --  -47.82  19.00-150.00   52
  4  ω    -43.00 -18.00   0.50   22.00    --  -86.25  45.00-120.00   50
  5  ω    -41.00 -15.00   0.50   22.00    --  -86.25  45.00 -90.00   52
  6  ω    -85.00 -50.00   0.50    4.57    --  -47.82 134.00 -75.00   70
  7  ω    109.00 134.00   0.50   22.00    --  107.75 134.00 104.00   50
  8  ω     97.00 126.00   0.50   22.00    --  107.75  45.00  30.00   58
  9  ω    139.00 177.00   0.50   22.00    --  107.75  45.00  30.00   76
 10  ω    109.00 134.00   0.50   22.00    --  107.75 134.00 -75.00   50
 11  ω    142.00 168.00   0.50   22.00    --  107.75  61.00 -90.00   52
 12  ω    102.00 127.00   0.50   22.00    --  107.75  61.00 -90.00   50
 13  ω     96.00 177.00   0.50   22.00    --  107.75  45.00 -60.00  162
 14  ω     95.00 176.00   0.50   22.00    --  107.75  15.00 120.00  162
 15  ω     68.00 107.00   0.50   22.00    --  107.75-102.00  -2.82   78
 16  ω     86.00 111.00   0.50   22.00    --  107.75-125.00 -30.00   50
 17  ω     71.00 106.00   0.50   22.00    --  107.75-125.00-120.00   70
 18  ω     78.00 104.00   0.50   22.00    --  107.75 -94.00-150.00   52
 19  ω     49.00 119.00   0.50   22.00    --  107.75-134.00-142.00  140
 20  ω     53.00  79.00   0.50   22.00    --  107.75 -61.00-150.00   52
 21  ω     35.00  74.00   0.50   22.00    --  107.75 -94.00-150.00   78
 22  ω     38.00 103.00   0.50   22.00    --  107.75 -94.00 -90.00  130
 23  ω     50.00  76.00   0.50   22.00    --  107.75 -61.00   0.00   52
 24  ω     36.00  82.00   0.50   22.00    --  107.75 -94.00 -30.00   92
 25  ω     39.00  80.00   0.50   22.00    --  107.75-134.00  37.00   82
 26  ω     36.00  79.00   0.50   22.00    --  107.75 -61.00  90.00   86
 27  ω     46.00  71.00   0.50    4.57    --   47.82-134.00  37.00   50
 28  ω     35.00  76.00   0.50   22.00    --  107.75-125.00 -30.00   82
 29  ω     43.00  79.00   0.50    4.57    --   47.82-134.00-142.00   72
 30  ω    -93.00 -68.00   0.50    4.57    --  -47.82-134.00  37.00   50
 31  ω   -117.00 -70.00   0.50    4.57    --  -47.82-134.00-142.00   94
 32  ω   -138.00-113.00   0.50   22.00    --  -86.25-134.00  37.00   50
 33  ω   -116.00 -76.00   0.50    4.57    --  -47.82-125.00 150.00   80
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0329378000
_diffrn_orient_matrix_UB_12      0.0215585000
_diffrn_orient_matrix_UB_13      0.1410259000
_diffrn_orient_matrix_UB_21      0.0115423000
_diffrn_orient_matrix_UB_22      0.0636298000
_diffrn_orient_matrix_UB_23      -0.0475607000
_diffrn_orient_matrix_UB_31      -0.1937211000
_diffrn_orient_matrix_UB_32      0.0000685000
_diffrn_orient_matrix_UB_33      -0.0891248000
_diffrn_oxdiff_digest_frames     
;
0174854a45ab953e30bc815101d11dac120002576ae
;
_diffrn_oxdiff_digest_hkl        
;
01d7d6991a8f0450c68ae52a85cf0da1f67286
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2982
_reflns_number_total             3550
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.463
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         3550
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0717
_refine_ls_R_factor_gt           0.0611
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1002P)²+0.7535P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1674
_refine_ls_wR_factor_ref         0.1757
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C15(H15), C17(H17),
 C19(H19)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.5259(2) 0.22677(7) 0.16781(17) 0.0420(4) Uani 1 1 d . . . . .
O2 O 0.5580(3) 0.43311(8) 0.5900(2) 0.0519(5) Uani 1 1 d . . . . .
O3 O 0.7947(3) 0.47676(9) 0.6130(2) 0.0629(6) Uani 1 1 d . . . . .
O4 O 1.2080(3) 0.37555(12) 0.4524(3) 0.0747(7) Uani 1 1 d . . . . .
O5 O 1.1015(3) 0.32135(10) 0.2519(3) 0.0719(7) Uani 1 1 d . . . . .
N1 N 0.0424(3) 0.19092(11) 0.2501(3) 0.0530(6) Uani 1 1 d . . . . .
N2 N 0.4719(2) 0.22437(8) 0.38401(19) 0.0288(4) Uani 1 1 d . . . . .
H2 H 0.492(4) 0.2395(13) 0.465(3) 0.042(7) Uiso 1 1 d . . . . .
N3 N 0.6937(3) 0.43587(9) 0.5711(2) 0.0442(5) Uani 1 1 d . . . . .
N4 N 1.0913(3) 0.34789(11) 0.3603(3) 0.0560(6) Uani 1 1 d . . . . .
C1 C 0.4217(2) 0.12688(9) 0.4721(2) 0.0300(4) Uani 1 1 d . . . . .
C2 C 0.5804(3) 0.09701(9) 0.5096(2) 0.0300(4) Uani 1 1 d . . . . .
C3 C 0.7017(3) 0.10852(9) 0.4404(2) 0.0321(4) Uani 1 1 d . . . . .
H3 H 0.676655 0.136797 0.362441 0.039 Uiso 1 1 calc R . . . .
C4 C 0.8544(3) 0.07956(10) 0.4840(3) 0.0394(5) Uani 1 1 d . . . . .
H4 H 0.934387 0.088091 0.436560 0.047 Uiso 1 1 calc R . . . .
C5 C 0.8940(3) 0.03748(11) 0.5980(3) 0.0446(6) Uani 1 1 d . . . . .
H5 H 1.001122 0.018009 0.628309 0.053 Uiso 1 1 calc R . . . .
C6 C 0.7796(3) 0.02436(10) 0.6654(3) 0.0435(6) Uani 1 1 d . . . . .
H6 H 0.806906 -0.004818 0.741302 0.052 Uiso 1 1 calc R . . . .
C7 C 0.6207(3) 0.05348(9) 0.6243(2) 0.0351(5) Uani 1 1 d . . . . .
C8 C 0.5020(3) 0.04137(11) 0.6960(2) 0.0425(6) Uani 1 1 d . . . . .
H8 H 0.525691 0.011024 0.768645 0.051 Uiso 1 1 calc R . . . .
C9 C 0.3559(3) 0.07214(12) 0.6630(3) 0.0442(6) Uani 1 1 d . . . . .
H9 H 0.280570 0.064617 0.715868 0.053 Uiso 1 1 calc R . . . .
C10 C 0.3145(3) 0.11548(11) 0.5502(2) 0.0373(5) Uani 1 1 d . . . . .
H10 H 0.211403 0.137008 0.527949 0.045 Uiso 1 1 calc R . . . .
C11 C 0.3724(2) 0.17089(9) 0.3437(2) 0.0304(4) Uani 1 1 d . . . . .
H11 H 0.397450 0.152722 0.258056 0.037 Uiso 1 1 calc R . . . .
C12 C 0.1865(3) 0.18332(10) 0.2908(2) 0.0388(5) Uani 1 1 d . . . . .
C13 C 0.5459(3) 0.24781(9) 0.2920(2) 0.0307(4) Uani 1 1 d . . . . .
C14 C 0.6612(3) 0.29873(9) 0.3514(2) 0.0317(4) Uani 1 1 d . . . . .
C15 C 0.6234(3) 0.34270(9) 0.4355(2) 0.0309(4) Uani 1 1 d . . . . .
H15 H 0.520259 0.341687 0.456169 0.037 Uiso 1 1 calc R . . . .
C16 C 0.7384(3) 0.38794(10) 0.4886(2) 0.0362(5) Uani 1 1 d . . . . .
C17 C 0.8919(3) 0.39076(11) 0.4666(3) 0.0416(5) Uani 1 1 d . . . . .
H17 H 0.970944 0.421459 0.507606 0.050 Uiso 1 1 calc R . . . .
C18 C 0.9252(3) 0.34710(11) 0.3825(3) 0.0420(6) Uani 1 1 d . . . . .
C19 C 0.8132(3) 0.30144(10) 0.3208(3) 0.0391(5) Uani 1 1 d . . . . .
H19 H 0.838793 0.272852 0.259472 0.047 Uiso 1 1 calc R . . . .


_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 C13 1.230(2) . ?
O2 N3 1.211(3) . ?
O3 N3 1.230(3) . ?
O4 N4 1.232(4) . ?
O5 N4 1.225(4) . ?
N1 C12 1.142(3) . ?
N2 H2 0.80(3) . ?
N2 C11 1.455(3) . ?
N2 C13 1.348(3) . ?
N3 C16 1.473(3) . ?
N4 C18 1.477(3) . ?
C1 C2 1.422(3) . ?
C1 C10 1.376(3) . ?
C1 C11 1.523(3) . ?
C2 C3 1.415(3) . ?
C2 C7 1.427(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.368(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.399(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.360(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.413(3) . ?
C7 C8 1.416(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.349(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.412(4) . ?
C10 H10 0.9500 . ?
C11 H11 1.0000 . ?
C11 C12 1.483(3) . ?
C13 C14 1.492(3) . ?
C14 C15 1.390(3) . ?
C14 C19 1.403(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.383(3) . ?
C16 C17 1.373(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.369(4) . ?
C18 C19 1.389(4) . ?
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
C11 N2 H2 121(2) . . ?
C13 N2 H2 117(2) . . ?
C13 N2 C11 121.10(17) . . ?
O2 N3 O3 124.4(2) . . ?
O2 N3 C16 117.9(2) . . ?
O3 N3 C16 117.7(2) . . ?
O4 N4 C18 117.0(3) . . ?
O5 N4 O4 125.4(2) . . ?
O5 N4 C18 117.6(3) . . ?
C2 C1 C11 118.93(17) . . ?
C10 C1 C2 120.1(2) . . ?
C10 C1 C11 120.92(19) . . ?
C1 C2 C7 118.39(18) . . ?
C3 C2 C1 123.56(19) . . ?
C3 C2 C7 118.0(2) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 C2 121.0(2) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 H4 119.7 . . ?
C3 C4 C5 120.6(2) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 H5 119.9 . . ?
C6 C5 C4 120.2(2) . . ?
C6 C5 H5 119.9 . . ?
C5 C6 H6 119.5 . . ?
C5 C6 C7 121.0(2) . . ?
C7 C6 H6 119.5 . . ?
C6 C7 C2 119.1(2) . . ?
C6 C7 C8 121.7(2) . . ?
C8 C7 C2 119.2(2) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 C7 121.2(2) . . ?
C9 C8 H8 119.4 . . ?
C8 C9 H9 119.9 . . ?
C8 C9 C10 120.3(2) . . ?
C10 C9 H9 119.9 . . ?
C1 C10 C9 120.7(2) . . ?
C1 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
N2 C11 C1 112.35(16) . . ?
N2 C11 H11 107.5 . . ?
N2 C11 C12 111.16(18) . . ?
C1 C11 H11 107.5 . . ?
C12 C11 C1 110.68(17) . . ?
C12 C11 H11 107.5 . . ?
N1 C12 C11 177.7(3) . . ?
O1 C13 N2 121.8(2) . . ?
O1 C13 C14 121.37(18) . . ?
N2 C13 C14 116.75(17) . . ?
C15 C14 C13 122.48(18) . . ?
C15 C14 C19 119.6(2) . . ?
C19 C14 C13 117.90(19) . . ?
C14 C15 H15 120.6 . . ?
C16 C15 C14 118.9(2) . . ?
C16 C15 H15 120.6 . . ?
C15 C16 N3 118.6(2) . . ?
C17 C16 N3 118.2(2) . . ?
C17 C16 C15 123.2(2) . . ?
C16 C17 H17 121.7 . . ?
C18 C17 C16 116.7(2) . . ?
C18 C17 H17 121.7 . . ?
C17 C18 N4 118.1(2) . . ?
C17 C18 C19 123.4(2) . . ?
C19 C18 N4 118.5(2) . . ?
C14 C19 H19 120.9 . . ?
C18 C19 C14 118.1(2) . . ?
C18 C19 H19 120.9 . . ?

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
_geom_hbond_publ_flag
N2 H2 O1 0.80(3) 2.00(3) 2.804(2) 175(3) 4_566 yes

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.824
_oxdiff_exptl_absorpt_empirical_full_min 0.552
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Hexane and Chloroform'
