# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_jl3_8
_database_code_depnum_ccdc_archive 'CCDC 1859965'
loop_
_audit_author_name
_audit_author_address
'Tilo Soehnel'
;The University of Auckland
New Zealand
;
_audit_update_record             
;
2021-12-02 deposited with the CCDC.	2022-01-17 downloaded from the CCDC.
;
_audit_creation_date             2021-12-01
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H22 N4 O2'
_chemical_formula_sum            'C23 H22 N4 O2'
_chemical_formula_weight         386.44
_chemical_melting_point          ?
_chemical_oxdiff_formula         C23H22N4O2
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/n 1'
_space_group_name_Hall           '-P 2yn'
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                   12.0831(2)
_cell_length_b                   9.0813(2)
_cell_length_c                   18.4230(3)
_cell_angle_alpha                90
_cell_angle_beta                 102.333(2)
_cell_angle_gamma                90
_cell_volume                     1974.91(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9085
_cell_measurement_temperature    109(2)
_cell_measurement_theta_max      74.3610
_cell_measurement_theta_min      4.0420
_shelx_estimated_absorpt_T_max   0.935
_shelx_estimated_absorpt_T_min   0.811
_exptl_absorpt_coefficient_mu    0.685
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67396
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.44a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            13539
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.737
_diffrn_reflns_theta_min         6.149
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      109(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    104.00 132.00   0.50    0.49    --  102.39 111.00-150.00   56
  2  ω    141.00 166.00   0.50    0.49    --  102.39 111.00-150.00   50
  3  ω    100.00 164.00   0.50    0.49    --  102.39 111.00 -90.00  128
  4  ω    102.00 143.00   0.50    0.49    --  102.39 111.00 -60.00   82
  5  ω     79.00 115.00   0.50    0.49    --  102.39-111.00  60.00   72
  6  ω     63.00 109.00   0.50    0.49    --  102.39 -95.00 120.00   92
  7  ω     27.00  53.00   0.50    0.49    --  102.39-111.00  60.00   52
  8  ω      1.00  84.00   0.50    0.12    --   47.48 -99.00 150.00  166
  9  ω   -123.00 -74.00   0.50    0.12    --  -47.48-125.00 150.00   98
 10  ω   -124.00 -73.00   0.50    0.12    --  -47.48-125.00 120.00  102
 11  ω   -123.00 -70.00   0.50    0.12    --  -47.48-125.00 -60.00  106
 12  ω   -115.00 -72.00   0.50    0.12    --  -47.48-125.00-180.00   86
 13  ω   -136.00 -90.00   0.50    0.49    --  -90.25 -95.00-180.00   92
 14  ω   -141.00-116.00   0.50    0.49    --  -90.25 -59.00-141.00   50
 15  ω    -19.00  28.00   0.50    0.12    --   47.48 -59.00-141.00   94
 16  ω     55.00  99.00   0.50    0.49    --  102.39 -59.00-141.00   88
 17  ω     29.00 122.00   0.50    0.49    --  102.39 -45.00-150.00  186
 18  ω    -98.00 -73.00   0.50    0.12    --  -47.48 -59.00-141.00   50
 19  ω   -105.00 -53.00   0.50    0.49    --  -90.25  59.00  -1.00  104
 20  ω    -92.00 -66.00   0.50    0.49    --  -90.25  45.00 120.00   52
 21  ω     55.00  80.00   0.50    0.12    --   47.48  59.00  -1.00   50
 22  ω     83.00 163.00   0.50    0.49    --  102.39  30.00  90.00  160
 23  ω     81.00 173.00   0.50    0.49    --  102.39  59.00  -1.00  184
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1073698000
_diffrn_orient_matrix_UB_12      0.0366225000
_diffrn_orient_matrix_UB_13      0.0590166000
_diffrn_orient_matrix_UB_21      -0.0354700000
_diffrn_orient_matrix_UB_22      -0.1124738000
_diffrn_orient_matrix_UB_23      0.0533842000
_diffrn_orient_matrix_UB_31      0.0650729000
_diffrn_orient_matrix_UB_32      -0.1216776000
_diffrn_orient_matrix_UB_33      -0.0315517000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\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                3170
_reflns_number_total             3567
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.39.44a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.44a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.44a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         3567
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0366
_refine_ls_restrained_S_all      1.067
_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)+(0.0499P)²+0.5149P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0941
_refine_ls_wR_factor_ref         0.0974
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C17(H17), C20(H20), C21(H21), C22(H22),
 C23(H23), N3(H3A)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C12(H12A,H12B,H12C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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
C1 C 0.57341(10) 0.84462(14) 0.34365(7) 0.0239(3) Uani 1 1 d . . . . .
H1 H 0.504940 0.875862 0.353720 0.029 Uiso 1 1 calc R U . . .
C2 C 0.62011(11) 0.92051(15) 0.29282(7) 0.0269(3) Uani 1 1 d . . . . .
H2 H 0.582734 1.001370 0.267942 0.032 Uiso 1 1 calc R U . . .
C3 C 0.72411(11) 0.87507(14) 0.27893(7) 0.0261(3) Uani 1 1 d . . . . .
H3 H 0.756622 0.927744 0.245539 0.031 Uiso 1 1 calc R U . . .
C4 C 0.77916(10) 0.75344(14) 0.31396(7) 0.0231(3) Uani 1 1 d . . . . .
H4 H 0.848093 0.723952 0.303973 0.028 Uiso 1 1 calc R U . . .
C5 C 0.73087(10) 0.67408(13) 0.36482(6) 0.0198(3) Uani 1 1 d . . . . .
C6 C 0.62788(10) 0.72078(13) 0.38039(6) 0.0204(3) Uani 1 1 d . . . . .
C7 C 0.57787(10) 0.63255(13) 0.43204(7) 0.0203(3) Uani 1 1 d . . . . .
C8 C 0.75750(10) 0.48870(13) 0.46449(6) 0.0192(3) Uani 1 1 d . . . . .
C9 C 0.78840(10) 0.32533(13) 0.47051(7) 0.0212(3) Uani 1 1 d . . . . .
C10 C 0.72412(12) 0.21829(15) 0.41616(8) 0.0300(3) Uani 1 1 d . . . . .
H10A H 0.753357 0.120945 0.428114 0.045 Uiso 1 1 calc R U . . .
H10B H 0.732077 0.243900 0.366982 0.045 Uiso 1 1 calc R U . . .
H10C H 0.645479 0.221037 0.418373 0.045 Uiso 1 1 calc R U . . .
C11 C 0.87831(10) 0.30421(14) 0.52566(7) 0.0211(3) Uani 1 1 d . . . . .
C12 C 0.94468(11) 0.16761(15) 0.54943(7) 0.0272(3) Uani 1 1 d . . . . .
H12A H 0.901238 0.083252 0.528807 0.041 Uiso 1 1 calc R U . . .
H12B H 0.961359 0.161144 0.602673 0.041 Uiso 1 1 calc R U . . .
H12C H 1.014159 0.170504 0.532127 0.041 Uiso 1 1 calc R U . . .
C13 C 0.90894(10) 0.44720(14) 0.56469(6) 0.0199(3) Uani 1 1 d . . . . .
C14 C 0.83433(10) 0.70262(13) 0.55387(7) 0.0211(3) Uani 1 1 d . . . . .
H14A H 0.808096 0.763501 0.510335 0.025 Uiso 1 1 calc R U . . .
H14B H 0.911559 0.731371 0.575760 0.025 Uiso 1 1 calc R U . . .
C15 C 0.75977(11) 0.73124(14) 0.60999(7) 0.0245(3) Uani 1 1 d . . . . .
H15A H 0.685340 0.689026 0.591518 0.029 Uiso 1 1 calc R U . . .
H15B H 0.792833 0.683214 0.656612 0.029 Uiso 1 1 calc R U . . .
C16 C 0.74807(10) 0.89248(14) 0.62323(7) 0.0226(3) Uani 1 1 d . . . . .
C17 C 0.66759(11) 0.98351(16) 0.58378(7) 0.0280(3) Uani 1 1 d . . . . .
H17 H 0.609378 0.953546 0.544989 0.034 Uiso 1 1 calc R U . . .
C18 C 0.77681(11) 1.12902(14) 0.66710(7) 0.0253(3) Uani 1 1 d . . . . .
C19 C 0.82067(10) 0.98409(14) 0.67662(7) 0.0222(3) Uani 1 1 d . . . . .
C20 C 0.91998(11) 0.95872(15) 0.73041(7) 0.0277(3) Uani 1 1 d . . . . .
H20 H 0.951303 0.864904 0.737388 0.033 Uiso 1 1 calc R U . . .
C21 C 0.97030(13) 1.07565(17) 0.77276(8) 0.0349(3) Uani 1 1 d . . . . .
H21 H 1.036599 1.059928 0.808197 0.042 Uiso 1 1 calc R U . . .
C22 C 0.92393(13) 1.21730(17) 0.76364(8) 0.0359(3) Uani 1 1 d . . . . .
H22 H 0.959252 1.293302 0.793746 0.043 Uiso 1 1 calc R U . . .
C23 C 0.82687(13) 1.24655(15) 0.71091(8) 0.0332(3) Uani 1 1 d . . . . .
H23 H 0.796060 1.340736 0.704797 0.040 Uiso 1 1 calc R U . . .
N1 N 0.78149(9) 0.54682(11) 0.39659(6) 0.0207(2) Uani 1 1 d . . . . .
N2 N 0.83329(8) 0.54906(11) 0.53105(5) 0.0197(2) Uani 1 1 d . . . . .
N3 N 0.68430(9) 1.12574(13) 0.60923(7) 0.0307(3) Uani 1 1 d . . . . .
H3A H 0.643420 1.200395 0.591726 0.037 Uiso 1 1 calc R U . . .
N4 N 0.63904(8) 0.51633(12) 0.46449(6) 0.0198(2) Uani 1 1 d . . . . .
O1 O 0.48275(7) 0.65810(10) 0.44532(5) 0.0256(2) Uani 1 1 d . . . . .
O2 O 0.98828(7) 0.47137(10) 0.61752(5) 0.0247(2) Uani 1 1 d . . . . .
H4A H 0.6078(13) 0.4639(17) 0.4953(9) 0.026(4) Uiso 1 1 d . . . . .
H1A H 0.8505(15) 0.5348(18) 0.3934(9) 0.031(4) 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
C1 H1 0.9300 . ?
C1 C2 1.3769(18) . ?
C1 C6 1.4022(17) . ?
C2 H2 0.9300 . ?
C2 C3 1.3973(19) . ?
C3 H3 0.9300 . ?
C3 C4 1.3768(18) . ?
C4 H4 0.9300 . ?
C4 C5 1.4040(18) . ?
C5 C6 1.4012(17) . ?
C5 N1 1.3781(16) . ?
C6 C7 1.4690(17) . ?
C7 N4 1.3524(16) . ?
C7 O1 1.2469(15) . ?
C8 C9 1.5281(17) . ?
C8 N1 1.4432(15) . ?
C8 N2 1.4707(15) . ?
C8 N4 1.4531(15) . ?
C9 C10 1.4894(18) . ?
C9 C11 1.3334(17) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.4912(17) . ?
C11 C13 1.4922(18) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 N2 1.3540(15) . ?
C13 O2 1.2311(15) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.5316(17) . ?
C14 N2 1.4558(16) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.4961(18) . ?
C16 C17 1.3620(18) . ?
C16 C19 1.4356(18) . ?
C17 H17 0.9300 . ?
C17 N3 1.3742(19) . ?
C18 C19 1.4157(18) . ?
C18 C23 1.396(2) . ?
C18 N3 1.3704(18) . ?
C19 C20 1.4025(19) . ?
C20 H20 0.9300 . ?
C20 C21 1.380(2) . ?
C21 H21 0.9300 . ?
C21 C22 1.399(2) . ?
C22 H22 0.9300 . ?
C22 C23 1.380(2) . ?
C23 H23 0.9300 . ?
N1 H1A 0.856(18) . ?
N3 H3A 0.8600 . ?
N4 H4A 0.885(17) . ?

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 C1 H1 119.6 . . ?
C2 C1 C6 120.76(12) . . ?
C6 C1 H1 119.6 . . ?
C1 C2 H2 120.3 . . ?
C1 C2 C3 119.47(12) . . ?
C3 C2 H2 120.3 . . ?
C2 C3 H3 119.5 . . ?
C4 C3 C2 120.96(12) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 H4 120.1 . . ?
C3 C4 C5 119.78(11) . . ?
C5 C4 H4 120.1 . . ?
C6 C5 C4 119.68(11) . . ?
N1 C5 C4 120.26(11) . . ?
N1 C5 C6 119.99(11) . . ?
C1 C6 C7 122.31(11) . . ?
C5 C6 C1 119.32(11) . . ?
C5 C6 C7 118.28(11) . . ?
N4 C7 C6 116.77(10) . . ?
O1 C7 C6 123.33(11) . . ?
O1 C7 N4 119.88(11) . . ?
N1 C8 C9 109.07(9) . . ?
N1 C8 N2 112.45(10) . . ?
N1 C8 N4 108.48(9) . . ?
N2 C8 C9 101.68(9) . . ?
N4 C8 C9 113.14(10) . . ?
N4 C8 N2 111.94(9) . . ?
C10 C9 C8 120.04(10) . . ?
C11 C9 C8 109.97(11) . . ?
C11 C9 C10 129.89(12) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 C12 130.02(12) . . ?
C9 C11 C13 108.66(11) . . ?
C12 C11 C13 121.33(11) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N2 C13 C11 107.47(10) . . ?
O2 C13 C11 127.39(11) . . ?
O2 C13 N2 125.14(12) . . ?
H14A C14 H14B 107.8 . . ?
C15 C14 H14A 109.0 . . ?
C15 C14 H14B 109.0 . . ?
N2 C14 H14A 109.0 . . ?
N2 C14 H14B 109.0 . . ?
N2 C14 C15 112.79(10) . . ?
C14 C15 H15A 109.3 . . ?
C14 C15 H15B 109.3 . . ?
H15A C15 H15B 108.0 . . ?
C16 C15 C14 111.46(10) . . ?
C16 C15 H15A 109.3 . . ?
C16 C15 H15B 109.3 . . ?
C17 C16 C15 126.06(12) . . ?
C17 C16 C19 106.02(11) . . ?
C19 C16 C15 127.86(11) . . ?
C16 C17 H17 124.7 . . ?
C16 C17 N3 110.63(12) . . ?
N3 C17 H17 124.7 . . ?
C23 C18 C19 122.33(13) . . ?
N3 C18 C19 107.32(11) . . ?
N3 C18 C23 130.34(12) . . ?
C18 C19 C16 107.23(11) . . ?
C20 C19 C16 133.98(12) . . ?
C20 C19 C18 118.78(12) . . ?
C19 C20 H20 120.6 . . ?
C21 C20 C19 118.71(13) . . ?
C21 C20 H20 120.6 . . ?
C20 C21 H21 119.2 . . ?
C20 C21 C22 121.54(13) . . ?
C22 C21 H21 119.2 . . ?
C21 C22 H22 119.3 . . ?
C23 C22 C21 121.34(13) . . ?
C23 C22 H22 119.3 . . ?
C18 C23 H23 121.4 . . ?
C22 C23 C18 117.27(13) . . ?
C22 C23 H23 121.4 . . ?
C5 N1 C8 121.45(10) . . ?
C5 N1 H1A 115.4(11) . . ?
C8 N1 H1A 113.1(11) . . ?
C13 N2 C8 111.49(10) . . ?
C13 N2 C14 123.98(10) . . ?
C14 N2 C8 124.28(10) . . ?
C17 N3 H3A 125.6 . . ?
C18 N3 C17 108.78(11) . . ?
C18 N3 H3A 125.6 . . ?
C7 N4 C8 125.46(10) . . ?
C7 N4 H4A 115.8(10) . . ?
C8 N4 H4A 117.5(10) . . ?

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
C1 C2 C3 C4 1.6(2) . . . . ?
C1 C6 C7 N4 -179.50(11) . . . . ?
C1 C6 C7 O1 2.19(19) . . . . ?
C2 C1 C6 C5 -0.16(19) . . . . ?
C2 C1 C6 C7 -176.77(12) . . . . ?
C2 C3 C4 C5 -0.44(19) . . . . ?
C3 C4 C5 C6 -1.03(18) . . . . ?
C3 C4 C5 N1 175.82(11) . . . . ?
C4 C5 C6 C1 1.32(18) . . . . ?
C4 C5 C6 C7 178.07(11) . . . . ?
C4 C5 N1 C8 159.99(11) . . . . ?
C5 C6 C7 N4 3.86(16) . . . . ?
C5 C6 C7 O1 -174.45(11) . . . . ?
C6 C1 C2 C3 -1.3(2) . . . . ?
C6 C5 N1 C8 -23.18(17) . . . . ?
C6 C7 N4 C8 13.04(17) . . . . ?
C8 C9 C11 C12 -174.97(11) . . . . ?
C8 C9 C11 C13 4.57(13) . . . . ?
C9 C8 N1 C5 159.23(10) . . . . ?
C9 C8 N2 C13 8.51(12) . . . . ?
C9 C8 N2 C14 -177.11(10) . . . . ?
C9 C8 N4 C7 -152.40(11) . . . . ?
C9 C11 C13 N2 0.91(13) . . . . ?
C9 C11 C13 O2 -178.67(12) . . . . ?
C10 C9 C11 C12 1.6(2) . . . . ?
C10 C9 C11 C13 -178.90(12) . . . . ?
C11 C13 N2 C8 -6.27(12) . . . . ?
C11 C13 N2 C14 179.33(10) . . . . ?
C12 C11 C13 N2 -179.50(10) . . . . ?
C12 C11 C13 O2 0.92(18) . . . . ?
C14 C15 C16 C17 88.73(15) . . . . ?
C14 C15 C16 C19 -88.05(15) . . . . ?
C15 C14 N2 C8 94.26(13) . . . . ?
C15 C14 N2 C13 -92.05(13) . . . . ?
C15 C16 C17 N3 -177.84(11) . . . . ?
C15 C16 C19 C18 178.66(11) . . . . ?
C15 C16 C19 C20 0.5(2) . . . . ?
C16 C17 N3 C18 -0.62(15) . . . . ?
C16 C19 C20 C21 178.95(13) . . . . ?
C17 C16 C19 C18 1.37(13) . . . . ?
C17 C16 C19 C20 -176.82(13) . . . . ?
C18 C19 C20 C21 0.92(18) . . . . ?
C19 C16 C17 N3 -0.49(14) . . . . ?
C19 C18 C23 C22 1.55(19) . . . . ?
C19 C18 N3 C17 1.48(14) . . . . ?
C19 C20 C21 C22 0.6(2) . . . . ?
C20 C21 C22 C23 -1.2(2) . . . . ?
C21 C22 C23 C18 0.1(2) . . . . ?
C23 C18 C19 C16 179.41(11) . . . . ?
C23 C18 C19 C20 -2.07(18) . . . . ?
C23 C18 N3 C17 -179.82(13) . . . . ?
N1 C5 C6 C1 -175.53(11) . . . . ?
N1 C5 C6 C7 1.22(17) . . . . ?
N1 C8 C9 C10 -65.82(14) . . . . ?
N1 C8 C9 C11 111.10(11) . . . . ?
N1 C8 N2 C13 -108.00(11) . . . . ?
N1 C8 N2 C14 66.38(14) . . . . ?
N1 C8 N4 C7 -31.23(16) . . . . ?
N2 C8 C9 C10 175.23(11) . . . . ?
N2 C8 C9 C11 -7.85(12) . . . . ?
N2 C8 N1 C5 -88.78(13) . . . . ?
N2 C8 N4 C7 93.43(13) . . . . ?
N2 C14 C15 C16 -171.07(10) . . . . ?
N3 C18 C19 C16 -1.75(13) . . . . ?
N3 C18 C19 C20 176.76(11) . . . . ?
N3 C18 C23 C22 -176.98(13) . . . . ?
N4 C8 C9 C10 55.02(15) . . . . ?
N4 C8 C9 C11 -128.06(11) . . . . ?
N4 C8 N1 C5 35.58(15) . . . . ?
N4 C8 N2 C13 129.57(10) . . . . ?
N4 C8 N2 C14 -56.05(14) . . . . ?
O1 C7 N4 C8 -168.59(11) . . . . ?
O2 C13 N2 C8 173.31(11) . . . . ?
O2 C13 N2 C14 -1.08(18) . . . . ?

_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 1.294
_oxdiff_exptl_absorpt_empirical_full_min 0.632
####################################################################### 
# 
# 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_jl3_12b
_database_code_depnum_ccdc_archive 'CCDC 1859974'
loop_
_audit_author_name
_audit_author_address
'Tilo Soehnel'
;The University of Auckland
New Zealand
;
_audit_update_record             
;
2021-12-02 deposited with the CCDC.	2022-01-17 downloaded from the CCDC.
;
_audit_creation_date             2021-12-01
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H12 N2 O2'
_chemical_formula_sum            'C13 H12 N2 O2'
_chemical_formula_weight         228.25
_chemical_melting_point          ?
_chemical_oxdiff_formula         C13H12N2O2
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                   15.7052(8)
_cell_length_b                   5.0360(2)
_cell_length_c                   13.3544(6)
_cell_angle_alpha                90
_cell_angle_beta                 90.211(4)
_cell_angle_gamma                90
_cell_volume                     1056.21(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4020
_cell_measurement_temperature    99.9(5)
_cell_measurement_theta_max      75.3350
_cell_measurement_theta_min      5.6320
_shelx_estimated_absorpt_T_max   0.924
_shelx_estimated_absorpt_T_min   0.882
_exptl_absorpt_coefficient_mu    0.807
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77944
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.44a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0308
_diffrn_reflns_av_unetI/netI     0.0228
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8761
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.718
_diffrn_reflns_theta_min         5.634
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.9(5)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     24.00 120.00   0.50    0.27    --   46.98  77.00 -30.00  192
  2  ω    106.00 138.00   0.50    1.06    --  103.64 178.00-180.00   64
  3  ω     60.00  94.00   0.50    1.06    --  103.64 178.00-180.00   68
  4  ω     84.00 173.00   0.50    1.06    --  103.64  45.00  30.00  178
  5  ω     77.00 123.00   0.50    1.06    --  103.64 -61.00  30.00   92
  6  ω     34.00  64.00   0.50    1.06    --  103.64 -61.00  30.00   60
  7  ω    -88.00 -11.00   0.50    1.06    --  -90.25 111.00  30.00  154
  8  ω   -105.00 -15.00   0.50    1.06    --  -90.25  77.00 -90.00  180
  9  ω    -72.00 -16.00   0.50    0.27    --  -46.98  77.00 -90.00  112
 10  ω     27.00  68.00   0.50    1.06    --  103.64 -15.00 150.00   82
 11  ω     86.00 113.00   0.50    1.06    --  103.64-111.00 150.00   54
 12  ω     35.00 112.00   0.50    1.06    --  103.64-111.00   0.00  154
 13  ω     46.00 103.00   0.50    1.06    --  103.64 -95.00   0.00  114
 14  ω     69.00 104.00   0.50    1.06    --  103.64-111.00 -60.00   70
 15  ω     32.00  58.00   0.50    1.06    --  103.64-111.00-180.00   52
 16  ω     73.00 111.00   0.50    1.06    --  103.64-111.00-180.00   76
 17  ω     42.00  68.00   0.50    0.27    --   46.98-125.00 -90.00   52
 18  ω     42.00  98.00   0.50    0.27    --   46.98-125.00  60.00  112
 19  ω     87.00 131.00   0.50    1.06    --  103.64 -15.00 150.00   88
 20  ω   -103.00 -22.00   0.50    0.27    --  -46.98 -77.00  60.00  162
 21  ω   -159.00 -70.00   0.50    1.06    --  -90.25 -61.00 150.00  178
 22  ω   -158.00-109.00   0.50    1.06    --  -90.25 -45.00 -30.00   98
 23  ω   -155.00-128.00   0.50    1.06    --  -90.25 -45.00-150.00   54
 24  ω   -158.00 -70.00   0.50    1.06    --  -90.25 -61.00-180.00  176
 25  ω   -106.00 -79.00   0.50    1.06    --  -90.25 -45.00-150.00   54
 26  ω     38.00  63.00   0.50    1.06    --  103.64-111.00 -90.00   50
 27  ω     64.00  90.00   0.50    1.06    --  103.64 -95.00 -60.00   52
 28  ω     30.00  60.00   0.50    1.06    --  103.64-111.00 150.00   60
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0235429000
_diffrn_orient_matrix_UB_12      -0.2349835000
_diffrn_orient_matrix_UB_13      0.0685224000
_diffrn_orient_matrix_UB_21      -0.0856472000
_diffrn_orient_matrix_UB_22      -0.1339949000
_diffrn_orient_matrix_UB_23      -0.0252539000
_diffrn_orient_matrix_UB_31      0.0417670000
_diffrn_orient_matrix_UB_32      -0.1425481000
_diffrn_orient_matrix_UB_33      -0.0892805000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\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                1785
_reflns_number_total             1894
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     67.62
_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 1.171.39.44a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.44a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.44a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.312
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         1894
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0565
_refine_ls_R_factor_gt           0.0544
_refine_ls_restrained_S_all      1.071
_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)+(0.0910P)²+0.8516P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1524
_refine_ls_wR_factor_ref         0.1545
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C12(H12A,H12B,H12C)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
C1 C 0.68477(12) 0.5388(4) 0.30516(14) 0.0233(4) Uani 1 1 d . . . . .
C2 C 0.65537(12) 0.7277(4) 0.23672(15) 0.0260(5) Uani 1 1 d . . . . .
H2 H 0.679996 0.737839 0.173614 0.031 Uiso 1 1 calc R U . . .
C3 C 0.59049(13) 0.8991(4) 0.26133(15) 0.0268(5) Uani 1 1 d . . . . .
H3 H 0.572273 1.025167 0.215113 0.032 Uiso 1 1 calc R U . . .
C4 C 0.55157(12) 0.8850(4) 0.35567(15) 0.0277(5) Uani 1 1 d . . . . .
H4 H 0.507234 0.999761 0.371557 0.033 Uiso 1 1 calc R U . . .
C5 C 0.57929(12) 0.7011(4) 0.42439(14) 0.0255(5) Uani 1 1 d . . . . .
H5 H 0.553725 0.692117 0.487004 0.031 Uiso 1 1 calc R U . . .
C6 C 0.64576(12) 0.5269(4) 0.40080(14) 0.0233(4) Uani 1 1 d . . . . .
C7 C 0.67610(12) 0.3358(4) 0.47513(14) 0.0248(5) Uani 1 1 d . . . . .
C8 C 0.79188(12) -0.0020(4) 0.50324(14) 0.0246(5) Uani 1 1 d . . . . .
H8 H 0.753611 -0.145573 0.523821 0.030 Uiso 1 1 calc R U . . .
C9 C 0.85694(12) -0.1034(4) 0.42902(14) 0.0249(5) Uani 1 1 d . . . . .
C10 C 0.92046(13) -0.3051(4) 0.46233(15) 0.0302(5) Uani 1 1 d . . . . .
H10A H 0.953995 -0.360515 0.406122 0.045 Uiso 1 1 calc R U . . .
H10B H 0.891307 -0.455760 0.489847 0.045 Uiso 1 1 calc R U . . .
H10C H 0.956982 -0.228937 0.512465 0.045 Uiso 1 1 calc R U . . .
C11 C 0.84785(12) 0.0150(4) 0.34001(14) 0.0243(5) Uani 1 1 d . . . . .
C12 C 0.89596(13) -0.0329(5) 0.24533(15) 0.0311(5) Uani 1 1 d . . . . .
H12A H 0.945968 -0.135843 0.259739 0.047 Uiso 1 1 calc R U . . .
H12B H 0.912339 0.134213 0.216639 0.047 Uiso 1 1 calc R U . . .
H12C H 0.860487 -0.127668 0.198828 0.047 Uiso 1 1 calc R U . . .
C13 C 0.77842(12) 0.2095(4) 0.34620(14) 0.0225(4) Uani 1 1 d . . . . .
N1 N 0.75147(10) 0.3697(3) 0.27751(12) 0.0235(4) Uani 1 1 d . . . . .
N2 N 0.74592(10) 0.1941(3) 0.44246(11) 0.0237(4) Uani 1 1 d . . . . .
O1 O 0.64692(9) 0.3008(3) 0.55925(10) 0.0301(4) Uani 1 1 d . . . . .
O2 O 0.83228(9) 0.1086(3) 0.58613(10) 0.0271(4) Uani 1 1 d . . . . .
H2A H 0.799448 0.109723 0.633733 0.041 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
C1 C2 1.397(3) . ?
C1 C6 1.420(3) . ?
C1 N1 1.401(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.376(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.404(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.374(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.400(3) . ?
C6 C7 1.461(3) . ?
C7 N2 1.380(3) . ?
C7 O1 1.228(2) . ?
C8 H8 0.9800 . ?
C8 C9 1.515(3) . ?
C8 N2 1.467(3) . ?
C8 O2 1.391(2) . ?
C9 C10 1.491(3) . ?
C9 C11 1.337(3) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.495(3) . ?
C11 C13 1.468(3) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 N1 1.292(3) . ?
C13 N2 1.387(2) . ?
O2 H2A 0.8200 . ?

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 C1 C6 118.34(18) . . ?
C2 C1 N1 119.17(17) . . ?
N1 C1 C6 122.49(18) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 C1 120.95(18) . . ?
C3 C2 H2 119.5 . . ?
C2 C3 H3 119.7 . . ?
C2 C3 C4 120.53(19) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 120.1 . . ?
C5 C4 C3 119.70(19) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 H5 119.8 . . ?
C4 C5 C6 120.45(18) . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C7 119.88(18) . . ?
C5 C6 C1 120.03(18) . . ?
C5 C6 C7 120.08(17) . . ?
N2 C7 C6 112.54(16) . . ?
O1 C7 C6 126.47(18) . . ?
O1 C7 N2 120.97(18) . . ?
C9 C8 H8 110.5 . . ?
N2 C8 H8 110.5 . . ?
N2 C8 C9 101.33(15) . . ?
O2 C8 H8 110.5 . . ?
O2 C8 C9 110.43(15) . . ?
O2 C8 N2 113.13(16) . . ?
C10 C9 C8 119.12(17) . . ?
C11 C9 C8 111.20(18) . . ?
C11 C9 C10 129.67(18) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 C12 128.86(19) . . ?
C9 C11 C13 108.92(17) . . ?
C13 C11 C12 122.20(17) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N1 C13 C11 128.18(17) . . ?
N1 C13 N2 124.92(18) . . ?
N2 C13 C11 106.89(16) . . ?
C13 N1 C1 115.84(16) . . ?
C7 N2 C8 124.27(16) . . ?
C7 N2 C13 124.01(17) . . ?
C13 N2 C8 111.63(16) . . ?
C8 O2 H2A 109.5 . . ?

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
C1 C2 C3 C4 -0.9(3) . . . . ?
C1 C6 C7 N2 3.6(3) . . . . ?
C1 C6 C7 O1 -178.19(19) . . . . ?
C2 C1 C6 C5 0.3(3) . . . . ?
C2 C1 C6 C7 -178.64(18) . . . . ?
C2 C1 N1 C13 176.48(18) . . . . ?
C2 C3 C4 C5 0.9(3) . . . . ?
C3 C4 C5 C6 -0.3(3) . . . . ?
C4 C5 C6 C1 -0.3(3) . . . . ?
C4 C5 C6 C7 178.64(18) . . . . ?
C5 C6 C7 N2 -175.30(17) . . . . ?
C5 C6 C7 O1 2.9(3) . . . . ?
C6 C1 C2 C3 0.3(3) . . . . ?
C6 C1 N1 C13 -3.2(3) . . . . ?
C6 C7 N2 C8 177.10(17) . . . . ?
C6 C7 N2 C13 -6.5(3) . . . . ?
C8 C9 C11 C12 -177.4(2) . . . . ?
C8 C9 C11 C13 1.5(2) . . . . ?
C9 C8 N2 C7 176.63(17) . . . . ?
C9 C8 N2 C13 -0.1(2) . . . . ?
C9 C11 C13 N1 177.77(19) . . . . ?
C9 C11 C13 N2 -1.5(2) . . . . ?
C10 C9 C11 C12 4.1(4) . . . . ?
C10 C9 C11 C13 -177.1(2) . . . . ?
C11 C13 N1 C1 -178.73(18) . . . . ?
C11 C13 N2 C7 -175.80(17) . . . . ?
C11 C13 N2 C8 1.0(2) . . . . ?
C12 C11 C13 N1 -3.3(3) . . . . ?
C12 C11 C13 N2 177.43(18) . . . . ?
N1 C1 C2 C3 -179.41(18) . . . . ?
N1 C1 C6 C5 179.98(17) . . . . ?
N1 C1 C6 C7 1.0(3) . . . . ?
N1 C13 N2 C7 4.9(3) . . . . ?
N1 C13 N2 C8 -178.35(18) . . . . ?
N2 C8 C9 C10 177.87(17) . . . . ?
N2 C8 C9 C11 -0.9(2) . . . . ?
N2 C13 N1 C1 0.4(3) . . . . ?
O1 C7 N2 C8 -1.2(3) . . . . ?
O1 C7 N2 C13 175.19(18) . . . . ?
O2 C8 C9 C10 57.7(2) . . . . ?
O2 C8 C9 C11 -120.99(19) . . . . ?
O2 C8 N2 C7 -65.2(2) . . . . ?
O2 C8 N2 C13 118.06(17) . . . . ?

_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 1.354
_oxdiff_exptl_absorpt_empirical_full_min 0.755
####################################################################### 
# 
# 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_jls_37_1
_database_code_depnum_ccdc_archive 'CCDC 2087701'
loop_
_audit_author_name
_audit_author_address
'Tilo Soehnel'
;The University of Auckland
New Zealand
;
_audit_update_record             
;
2021-12-02 deposited with the CCDC.	2022-01-17 downloaded from the CCDC.
;
_audit_creation_date             2021-12-01
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H20 N4 O'
_chemical_formula_sum            'C21 H20 N4 O'
_chemical_formula_weight         344.41
_chemical_melting_point          ?
_chemical_oxdiff_formula         C21H20N4O
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/n 1'
_space_group_name_Hall           '-P 2yn'
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                   13.5402(3)
_cell_length_b                   7.8769(2)
_cell_length_c                   16.4206(4)
_cell_angle_alpha                90
_cell_angle_beta                 105.285(2)
_cell_angle_gamma                90
_cell_volume                     1689.38(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10013
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.1340
_cell_measurement_theta_min      3.8040
_shelx_estimated_absorpt_T_max   0.993
_shelx_estimated_absorpt_T_min   0.967
_exptl_absorpt_coefficient_mu    0.686
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66570
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.23a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0602
_diffrn_reflns_av_unetI/netI     0.0344
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            19105
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.673
_diffrn_reflns_theta_max         67.673
_diffrn_reflns_theta_min         3.776
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -117.00 -49.00   0.50    0.15    --  -47.48 -74.00 144.00  136
  2  ω    -47.00   6.00   0.50    0.15    --  -47.48  74.00 -87.00  106
  3  ω    -10.00  72.00   0.50    0.15    --   47.48 -74.00 144.00  164
  4  ω   -164.00 -66.00   0.50    0.58    --  -90.25 -74.00 144.00  196
  5  ω     47.00  89.00   0.50    0.58    --  101.53 -74.00 144.00   84
  6  ω    133.00 177.00   0.50    0.58    --  101.53  74.00 -87.00   88
  7  ω     86.00 123.00   0.50    0.58    --  101.53  74.00 -87.00   74
  8  ω   -124.00 -71.00   0.50    0.15    --  -47.48-125.00  90.00  106
  9  ω   -124.00 -70.00   0.50    0.15    --  -47.48-125.00-150.00  108
 10  ω     40.00 121.00   0.50    0.15    --   47.48  57.00 -30.00  162
 11  ω    -10.00  28.00   0.50    0.15    --   47.48 -38.00 150.00   76
 12  ω    -87.00 -11.00   0.50    0.58    --  -90.25 111.00 -90.00  152
 13  ω   -153.00 -91.00   0.50    0.58    --  -90.25 -61.00   0.00  124
 14  ω   -127.00-100.00   0.50    0.58    --  -90.25 -94.00  60.00   54
 15  ω   -117.00 -71.00   0.50    0.58    --  -90.25 -30.00  30.00   92
 16  ω    -91.00 -65.00   0.50    0.58    --  -90.25  74.00 -87.00   52
 17  ω   -159.00-112.00   0.50    0.58    --  -90.25 -77.00  90.00   94
 18  ω    -82.00 -37.00   0.50    0.58    --  -90.25  61.00 120.00   90
 19  ω     86.00 174.00   0.50    0.58    --  101.53  30.00  60.00  176
 20  ω     82.00 176.00   0.50    0.58    --  101.53  45.00-120.00  188
 21  ω    124.00 172.00   0.50    0.58    --  101.53  77.00-180.00   96
 22  ω     25.00 111.00   0.50    0.58    --  101.53-111.00 120.00  172
 23  ω     82.00 110.00   0.50    0.58    --  101.53  77.00-180.00   56
 24  ω     82.00 111.00   0.50    0.58    --  101.53  30.00-150.00   58
 25  ω    129.00 176.00   0.50    0.58    --  101.53 111.00  30.00   94
 26  ω     95.00 120.00   0.50    0.58    --  101.53 -61.00  30.00   50
 27  ω     42.00  75.00   0.50    0.58    --  101.53 -61.00  30.00   66
 28  ω     25.00  90.00   0.50    0.58    --  101.53 -45.00 150.00  130
 29  ω     85.00 147.00   0.50    0.58    --  101.53  30.00   0.00  124
 30  ω     37.00 122.00   0.50    0.58    --  101.53 -61.00 150.00  170
 31  ω     91.00 158.00   0.50    0.58    --  101.53  61.00   0.00  134
 32  ω    121.00 164.00   0.50    0.58    --  101.53  30.00-150.00   86
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0521524000
_diffrn_orient_matrix_UB_12      0.1412104000
_diffrn_orient_matrix_UB_13      0.0613497000
_diffrn_orient_matrix_UB_21      0.0440204000
_diffrn_orient_matrix_UB_22      0.0765975000
_diffrn_orient_matrix_UB_23      -0.0692766000
_diffrn_orient_matrix_UB_31      -0.0962085000
_diffrn_orient_matrix_UB_32      0.1116198000
_diffrn_orient_matrix_UB_33      -0.0298339000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\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                2822
_reflns_number_total             3053
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_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 1.171.40.23a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.23a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.23a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.382
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     243
_refine_ls_number_reflns         3053
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0473
_refine_ls_R_factor_gt           0.0447
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0808P)²+0.5055P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1213
_refine_ls_wR_factor_ref         0.1244
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C17(H17), C18(H18), C19(H19), C20(H20), N3(H3A)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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
C1 C 0.24868(10) 0.16102(17) 0.59926(9) 0.0196(3) Uani 1 1 d . . . . .
C2 C 0.19900(11) 0.18311(17) 0.51433(9) 0.0223(3) Uani 1 1 d . . . . .
H2 H 0.127984 0.179295 0.495192 0.027 Uiso 1 1 calc R U . . .
C3 C 0.25919(11) 0.21101(18) 0.45928(9) 0.0245(3) Uani 1 1 d . . . . .
H3 H 0.228139 0.228015 0.402223 0.029 Uiso 1 1 calc R U . . .
C4 C 0.36675(11) 0.21399(18) 0.48849(9) 0.0254(3) Uani 1 1 d . . . . .
H4 H 0.405471 0.232413 0.450210 0.030 Uiso 1 1 calc R U . . .
C5 C 0.41583(11) 0.19023(18) 0.57246(9) 0.0230(3) Uani 1 1 d . . . . .
H5 H 0.486941 0.191186 0.590689 0.028 Uiso 1 1 calc R U . . .
C6 C 0.35685(10) 0.16445(17) 0.63042(9) 0.0199(3) Uani 1 1 d . . . . .
C7 C 0.37876(10) 0.13787(16) 0.72001(9) 0.0192(3) Uani 1 1 d . . . . .
C8 C 0.28719(10) 0.11982(17) 0.73930(8) 0.0180(3) Uani 1 1 d . . . . .
C9 C 0.27218(9) 0.08047(17) 0.82477(8) 0.0185(3) Uani 1 1 d . . . . .
H9 H 0.235420 -0.027751 0.820173 0.022 Uiso 1 1 calc R U . . .
C10 C 0.47813(10) 0.12817(18) 0.78667(9) 0.0217(3) Uani 1 1 d . . . . .
H10A H 0.525144 0.213279 0.776294 0.026 Uiso 1 1 calc R U . . .
H10B H 0.508920 0.017250 0.785694 0.026 Uiso 1 1 calc R U . . .
C11 C 0.45744(10) 0.15880(18) 0.87264(9) 0.0218(3) Uani 1 1 d . . . . .
H11A H 0.519137 0.132985 0.916513 0.026 Uiso 1 1 calc R U . . .
H11B H 0.442268 0.278183 0.877367 0.026 Uiso 1 1 calc R U . . .
C12 C 0.20659(10) 0.21463(17) 0.85413(8) 0.0195(3) Uani 1 1 d . . . . .
H12A H 0.147120 0.239267 0.807854 0.023 Uiso 1 1 calc R U . . .
H12B H 0.246082 0.318447 0.867485 0.023 Uiso 1 1 calc R U . . .
C13 C 0.16992(10) 0.16121(19) 0.93192(9) 0.0221(3) Uani 1 1 d . . . . .
H13A H 0.099789 0.198936 0.923752 0.026 Uiso 1 1 calc R U . . .
H13B H 0.170048 0.038228 0.934995 0.026 Uiso 1 1 calc R U . . .
C14 C 0.23303(10) 0.22954(17) 1.01466(9) 0.0197(3) Uani 1 1 d . . . . .
C15 C 0.40670(10) 0.28104(17) 1.09748(9) 0.0198(3) Uani 1 1 d . . . . .
C16 C 0.36069(10) 0.35440(16) 1.16055(9) 0.0200(3) Uani 1 1 d . . . . .
C17 C 0.42090(11) 0.41811(18) 1.23705(9) 0.0241(3) Uani 1 1 d . . . . .
H17 H 0.491796 0.419740 1.247315 0.029 Uiso 1 1 calc R U . . .
C18 C 0.37572(11) 0.47853(19) 1.29737(9) 0.0262(3) Uani 1 1 d . . . . .
H18 H 0.415725 0.518901 1.348726 0.031 Uiso 1 1 calc R U . . .
C19 C 0.26842(11) 0.47828(18) 1.28017(9) 0.0256(3) Uani 1 1 d . . . . .
H19 H 0.237649 0.517851 1.320899 0.031 Uiso 1 1 calc R U . . .
C20 C 0.20856(11) 0.42114(18) 1.20493(9) 0.0240(3) Uani 1 1 d . . . . .
H20 H 0.137666 0.425123 1.194406 0.029 Uiso 1 1 calc R U . . .
C21 C 0.25323(10) 0.35587(17) 1.14276(9) 0.0204(3) Uani 1 1 d . . . . .
N1 N 0.20774(9) 0.13304(14) 0.66706(7) 0.0191(3) Uani 1 1 d . . . . .
N2 N 0.37219(8) 0.05715(15) 0.88753(7) 0.0197(3) Uani 1 1 d . . . . .
N3 N 0.33747(8) 0.21653(14) 1.02851(7) 0.0198(3) Uani 1 1 d . . . . .
H3A H 0.360557 0.164431 0.991325 0.024 Uiso 1 1 calc R U . . .
N4 N 0.18893(8) 0.29538(15) 1.06844(7) 0.0213(3) Uani 1 1 d . . . . .
O O 0.50018(7) 0.27261(13) 1.10454(6) 0.0243(3) Uani 1 1 d . . . . .
H2A H 0.3909(13) -0.049(2) 0.8908(10) 0.023(4) Uiso 1 1 d . . . . .
H1 H 0.1389(16) 0.137(3) 0.6627(12) 0.036(5) 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
C1 C2 1.390(2) . ?
C1 C6 1.4186(19) . ?
C1 N1 1.3859(17) . ?
C2 H2 0.9300 . ?
C2 C3 1.385(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.408(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.376(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.4091(19) . ?
C6 C7 1.4374(19) . ?
C7 C8 1.3655(18) . ?
C7 C10 1.4959(19) . ?
C8 C9 1.5026(17) . ?
C8 N1 1.3792(18) . ?
C9 H9 0.9800 . ?
C9 C12 1.5374(18) . ?
C9 N2 1.4811(17) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.5291(18) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 N2 1.4772(17) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.5459(18) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.5012(19) . ?
C14 N3 1.3757(17) . ?
C14 N4 1.2973(18) . ?
C15 C16 1.4611(18) . ?
C15 N3 1.3637(18) . ?
C15 O 1.2420(16) . ?
C16 C17 1.398(2) . ?
C16 C21 1.4066(19) . ?
C17 H17 0.9300 . ?
C17 C18 1.379(2) . ?
C18 H18 0.9300 . ?
C18 C19 1.405(2) . ?
C19 H19 0.9300 . ?
C19 C20 1.363(2) . ?
C20 H20 0.9300 . ?
C20 C21 1.4135(19) . ?
C21 N4 1.3836(18) . ?
N1 H1 0.92(2) . ?
N2 H2A 0.874(19) . ?
N3 H3A 0.8600 . ?

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 C1 C6 122.68(12) . . ?
N1 C1 C2 129.46(12) . . ?
N1 C1 C6 107.87(12) . . ?
C1 C2 H2 121.2 . . ?
C3 C2 C1 117.53(13) . . ?
C3 C2 H2 121.2 . . ?
C2 C3 H3 119.5 . . ?
C2 C3 C4 120.93(13) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 H4 119.3 . . ?
C5 C4 C3 121.45(13) . . ?
C5 C4 H4 119.3 . . ?
C4 C5 H5 120.5 . . ?
C4 C5 C6 119.10(13) . . ?
C6 C5 H5 120.5 . . ?
C1 C6 C7 106.34(12) . . ?
C5 C6 C1 118.31(13) . . ?
C5 C6 C7 135.36(13) . . ?
C6 C7 C10 131.26(12) . . ?
C8 C7 C6 107.31(12) . . ?
C8 C7 C10 121.43(12) . . ?
C7 C8 C9 126.35(12) . . ?
C7 C8 N1 110.04(12) . . ?
N1 C8 C9 123.51(11) . . ?
C8 C9 H9 107.4 . . ?
C8 C9 C12 112.50(11) . . ?
C12 C9 H9 107.4 . . ?
N2 C9 C8 110.58(10) . . ?
N2 C9 H9 107.4 . . ?
N2 C9 C12 111.40(11) . . ?
C7 C10 H10A 110.0 . . ?
C7 C10 H10B 110.0 . . ?
C7 C10 C11 108.61(11) . . ?
H10A C10 H10B 108.3 . . ?
C11 C10 H10A 110.0 . . ?
C11 C10 H10B 110.0 . . ?
C10 C11 H11A 108.7 . . ?
C10 C11 H11B 108.7 . . ?
H11A C11 H11B 107.6 . . ?
N2 C11 C10 114.12(11) . . ?
N2 C11 H11A 108.7 . . ?
N2 C11 H11B 108.7 . . ?
C9 C12 H12A 108.7 . . ?
C9 C12 H12B 108.7 . . ?
C9 C12 C13 114.20(11) . . ?
H12A C12 H12B 107.6 . . ?
C13 C12 H12A 108.7 . . ?
C13 C12 H12B 108.7 . . ?
C12 C13 H13A 108.6 . . ?
C12 C13 H13B 108.6 . . ?
H13A C13 H13B 107.5 . . ?
C14 C13 C12 114.84(11) . . ?
C14 C13 H13A 108.6 . . ?
C14 C13 H13B 108.6 . . ?
N3 C14 C13 115.97(11) . . ?
N4 C14 C13 120.33(12) . . ?
N4 C14 N3 123.70(13) . . ?
N3 C15 C16 114.07(12) . . ?
O C15 C16 124.71(13) . . ?
O C15 N3 121.21(12) . . ?
C17 C16 C15 121.49(12) . . ?
C17 C16 C21 120.65(12) . . ?
C21 C16 C15 117.84(12) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 C16 120.36(13) . . ?
C18 C17 H17 119.8 . . ?
C17 C18 H18 120.5 . . ?
C17 C18 C19 119.09(13) . . ?
C19 C18 H18 120.5 . . ?
C18 C19 H19 119.4 . . ?
C20 C19 C18 121.25(13) . . ?
C20 C19 H19 119.4 . . ?
C19 C20 H20 119.7 . . ?
C19 C20 C21 120.63(13) . . ?
C21 C20 H20 119.7 . . ?
C16 C21 C20 117.98(13) . . ?
N4 C21 C16 123.80(12) . . ?
N4 C21 C20 118.22(12) . . ?
C1 N1 H1 123.1(12) . . ?
C8 N1 C1 108.45(11) . . ?
C8 N1 H1 128.0(12) . . ?
C9 N2 H2A 111.0(11) . . ?
C11 N2 C9 115.38(11) . . ?
C11 N2 H2A 107.7(11) . . ?
C14 N3 H3A 117.9 . . ?
C15 N3 C14 124.13(11) . . ?
C15 N3 H3A 117.9 . . ?
C14 N4 C21 116.26(11) . . ?

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
C1 C2 C3 C4 1.0(2) . . . . ?
C1 C6 C7 C8 0.06(15) . . . . ?
C1 C6 C7 C10 179.84(13) . . . . ?
C2 C1 C6 C5 -0.4(2) . . . . ?
C2 C1 C6 C7 179.80(12) . . . . ?
C2 C1 N1 C8 -179.73(13) . . . . ?
C2 C3 C4 C5 -0.3(2) . . . . ?
C3 C4 C5 C6 -0.8(2) . . . . ?
C4 C5 C6 C1 1.1(2) . . . . ?
C4 C5 C6 C7 -179.19(15) . . . . ?
C5 C6 C7 C8 -179.65(15) . . . . ?
C5 C6 C7 C10 0.1(3) . . . . ?
C6 C1 C2 C3 -0.6(2) . . . . ?
C6 C1 N1 C8 0.27(14) . . . . ?
C6 C7 C8 C9 176.54(12) . . . . ?
C6 C7 C8 N1 0.11(15) . . . . ?
C6 C7 C10 C11 160.82(14) . . . . ?
C7 C8 C9 C12 123.36(14) . . . . ?
C7 C8 C9 N2 -1.91(19) . . . . ?
C7 C8 N1 C1 -0.24(15) . . . . ?
C7 C10 C11 N2 48.52(16) . . . . ?
C8 C7 C10 C11 -19.43(18) . . . . ?
C8 C9 C12 C13 167.63(11) . . . . ?
C8 C9 N2 C11 31.51(15) . . . . ?
C9 C8 N1 C1 -176.80(12) . . . . ?
C9 C12 C13 C14 98.34(14) . . . . ?
C10 C7 C8 C9 -3.3(2) . . . . ?
C10 C7 C8 N1 -179.70(12) . . . . ?
C10 C11 N2 C9 -57.63(16) . . . . ?
C12 C9 N2 C11 -94.38(13) . . . . ?
C12 C13 C14 N3 -45.95(17) . . . . ?
C12 C13 C14 N4 134.31(13) . . . . ?
C13 C14 N3 C15 175.74(12) . . . . ?
C13 C14 N4 C21 -179.66(12) . . . . ?
C15 C16 C17 C18 -176.59(13) . . . . ?
C15 C16 C21 C20 177.75(12) . . . . ?
C15 C16 C21 N4 -1.5(2) . . . . ?
C16 C15 N3 C14 4.96(19) . . . . ?
C16 C17 C18 C19 -1.3(2) . . . . ?
C16 C21 N4 C14 2.2(2) . . . . ?
C17 C16 C21 C20 -0.9(2) . . . . ?
C17 C16 C21 N4 179.86(13) . . . . ?
C17 C18 C19 C20 -0.6(2) . . . . ?
C18 C19 C20 C21 1.8(2) . . . . ?
C19 C20 C21 C16 -1.0(2) . . . . ?
C19 C20 C21 N4 178.29(13) . . . . ?
C20 C21 N4 C14 -176.97(12) . . . . ?
C21 C16 C17 C18 2.0(2) . . . . ?
N1 C1 C2 C3 179.37(13) . . . . ?
N1 C1 C6 C5 179.56(12) . . . . ?
N1 C1 C6 C7 -0.20(14) . . . . ?
N1 C8 C9 C12 -60.65(16) . . . . ?
N1 C8 C9 N2 174.08(12) . . . . ?
N2 C9 C12 C13 -67.54(14) . . . . ?
N3 C14 N4 C21 0.6(2) . . . . ?
N3 C15 C16 C17 176.63(12) . . . . ?
N3 C15 C16 C21 -2.05(18) . . . . ?
N4 C14 N3 C15 -4.5(2) . . . . ?
O C15 C16 C17 -1.9(2) . . . . ?
O C15 C16 C21 179.40(12) . . . . ?
O C15 N3 C14 -176.43(12) . . . . ?

_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 1.403
_oxdiff_exptl_absorpt_empirical_full_min 0.695
