# Electronic Supplementary Material (ESI) for Materials Chemistry Frontiers.
# This journal is © the Partner Organisations 2021

####################################################################### 
# 
# 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_L1
_database_code_depnum_ccdc_archive 'CCDC 2048284'
loop_
_audit_author_name
_audit_author_address
'June  Lovitt'
;Trinity College Dublin
Republic of Ireland
;
_audit_update_record             
;
2020-12-04 deposited with the CCDC.	2021-03-15 downloaded from the CCDC.
;
###### original file name data_jil048049
_audit_creation_date             2020-12-01
_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         'C22 H19 N3 O3, 4(H2 O)'
_chemical_formula_sum            'C22 H27 N3 O7'
_chemical_formula_weight         445.46
_chemical_absolute_configuration ad
_chemical_melting_point          ?
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                   4.4753(3)
_cell_length_b                   14.6485(8)
_cell_length_c                   16.3368(9)
_cell_angle_alpha                90
_cell_angle_beta                 90.416(4)
_cell_angle_gamma                90
_cell_volume                     1070.95(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4160
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      55.52
_cell_measurement_theta_min      4.05
_shelx_estimated_absorpt_T_max   0.958
_shelx_estimated_absorpt_T_min   0.942
_exptl_absorpt_coefficient_mu    0.867
_exptl_absorpt_correction_T_max  0.7510
_exptl_absorpt_correction_T_min  0.6681
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Krause, 2015) was used for absorption correction.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0724
_diffrn_reflns_av_unetI/netI     0.0401
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            3911
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         69.440
_diffrn_reflns_theta_min         2.705
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 8.33
_diffrn_detector_type            APEX2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device       'Kappa diffractometer'
_diffrn_measurement_device_type  'Bruker APEX2 Kappa Duo'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_detector       APEX2
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_special_details          ?
_diffrn_standards_number         .
_reflns_Friedel_coverage         0.885
_reflns_Friedel_fraction_full    0.977
_reflns_Friedel_fraction_max     0.949
_reflns_number_gt                3387
_reflns_number_total             3911
_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       'SAINT v8.38A (Bruker, 2016)'
_computing_data_collection       'APEX 3 (Bruker, 2017)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_refine_diff_density_max         0.146
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 
;
 Flack x determined using 1384 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.08(13)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     305
_refine_ls_number_reflns         3911
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0394
_refine_ls_restrained_S_all      1.017
_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)+(0.0579P)²+0.1839P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0962
_refine_ls_wR_factor_ref         0.1024
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Free rotating group:
 O30(H30A,H30B), O29(H29B,H29A), O31(H31A,H31B), O32(H32A,H32B)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C24(H24A,H24B), C25(H25A,H25B), C27(H27A,H27B), C28(H28A,H28B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C12(H12), C13(H13), C14(H14), C20(H20), C21(H21)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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
N1 N 0.4403(7) 0.4962(2) 0.07112(18) 0.0401(7) Uani 1 1 d . . . . .
C2 C 0.5351(8) 0.4097(3) 0.0723(2) 0.0389(8) Uani 1 1 d . . . . .
H2 H 0.670(8) 0.393(3) 0.029(2) 0.032(9) Uiso 1 1 d . . . . .
C3 C 0.4454(8) 0.3468(2) 0.1300(2) 0.0376(8) Uani 1 1 d . . . . .
H3 H 0.518217 0.285943 0.128976 0.045 Uiso 1 1 calc R . . . .
C4 C 0.2468(8) 0.3748(2) 0.1895(2) 0.0355(7) Uani 1 1 d . . . . .
H4 H 0.179544 0.332814 0.229688 0.043 Uiso 1 1 calc R . . . .
C5 C 0.1462(7) 0.4646(2) 0.1902(2) 0.0326(7) Uani 1 1 d . . . . .
C6 C 0.2499(7) 0.5222(2) 0.1295(2) 0.0363(8) Uani 1 1 d . . . . .
H6 H 0.182184 0.583666 0.129293 0.044 Uiso 1 1 calc R . . . .
C7 C -0.0729(7) 0.4986(2) 0.2527(2) 0.0331(7) Uani 1 1 d . . . . .
H7A H -0.105473 0.564852 0.244413 0.040 Uiso 1 1 calc R . . . .
H7B H -0.266776 0.467347 0.244369 0.040 Uiso 1 1 calc R . . . .
N8 N 0.0319(6) 0.48276(18) 0.33779(17) 0.0309(6) Uani 1 1 d . . . . .
C9 C 0.2363(7) 0.5451(2) 0.3700(2) 0.0308(7) Uani 1 1 d . . . . .
O10 O 0.3225(5) 0.60870(16) 0.32713(14) 0.0367(5) Uani 1 1 d . . . . .
C11 C 0.3350(7) 0.5311(2) 0.4550(2) 0.0287(7) Uani 1 1 d . . . . .
C12 C 0.5344(7) 0.5921(2) 0.4905(2) 0.0322(7) Uani 1 1 d . . . . .
H12 H 0.604740 0.642779 0.459849 0.039 Uiso 1 1 calc R . . . .
C13 C 0.6324(7) 0.5794(2) 0.5710(2) 0.0340(7) Uani 1 1 d . . . . .
H13 H 0.772527 0.620764 0.594340 0.041 Uiso 1 1 calc R . . . .
C14 C 0.5279(7) 0.5075(2) 0.6168(2) 0.0323(7) Uani 1 1 d . . . . .
H14 H 0.596882 0.499726 0.671496 0.039 Uiso 1 1 calc R . . . .
C15 C 0.3184(7) 0.4448(2) 0.5833(2) 0.0290(7) Uani 1 1 d . . . . .
C16 C 0.2276(7) 0.4565(2) 0.5007(2) 0.0286(7) Uani 1 1 d . . . . .
C17 C 0.0300(7) 0.3928(2) 0.4633(2) 0.0302(7) Uani 1 1 d . . . . .
C18 C -0.0763(7) 0.4066(2) 0.3797(2) 0.0310(7) Uani 1 1 d . . . . .
O19 O -0.2567(5) 0.35532(17) 0.34531(14) 0.0405(6) Uani 1 1 d . . . . .
C20 C -0.0621(7) 0.3178(2) 0.5074(2) 0.0350(8) Uani 1 1 d . . . . .
H20 H -0.186541 0.273575 0.481811 0.042 Uiso 1 1 calc R . . . .
C21 C 0.0233(8) 0.3057(2) 0.5887(2) 0.0343(7) Uani 1 1 d . . . . .
H21 H -0.042966 0.253055 0.617197 0.041 Uiso 1 1 calc R . . . .
C22 C 0.2025(7) 0.3684(2) 0.6289(2) 0.0312(7) Uani 1 1 d . . . . .
N23 N 0.2772(6) 0.36141(18) 0.71268(16) 0.0316(6) Uani 1 1 d . . . . .
C24 C 0.1319(8) 0.4311(2) 0.7649(2) 0.0350(7) Uani 1 1 d . . . . .
H24A H -0.086891 0.421138 0.764637 0.042 Uiso 1 1 calc R . . . .
H24B H 0.170969 0.492664 0.742342 0.042 Uiso 1 1 calc R . . . .
C25 C 0.2488(8) 0.4259(2) 0.8513(2) 0.0387(8) Uani 1 1 d . . . . .
H25A H 0.464398 0.441129 0.851950 0.046 Uiso 1 1 calc R . . . .
H25B H 0.143808 0.471420 0.885425 0.046 Uiso 1 1 calc R . . . .
O26 O 0.2068(6) 0.33693(17) 0.88510(15) 0.0409(6) Uani 1 1 d . . . . .
C27 C 0.3554(8) 0.2708(2) 0.8356(2) 0.0403(8) Uani 1 1 d . . . . .
H27A H 0.330109 0.209437 0.860053 0.048 Uiso 1 1 calc R . . . .
H27B H 0.571787 0.284623 0.834301 0.048 Uiso 1 1 calc R . . . .
C28 C 0.2316(8) 0.2705(2) 0.7492(2) 0.0361(8) Uani 1 1 d . . . . .
H28A H 0.334895 0.223593 0.716220 0.043 Uiso 1 1 calc R . . . .
H28B H 0.015760 0.255729 0.749913 0.043 Uiso 1 1 calc R . . . .
O30 O 0.5896(6) 0.63307(18) -0.03716(16) 0.0458(6) Uani 1 1 d . . . . .
H30A H 0.569703 0.588107 -0.002858 0.069 Uiso 1 1 d G . . . .
H30B H 0.437025 0.668260 -0.027738 0.069 Uiso 1 1 d G . . . .
O29 O 0.0960(6) 0.7287(2) 0.0012(2) 0.0541(7) Uani 1 1 d . . . . .
H29B H 0.048004 0.770776 0.036321 0.081 Uiso 1 1 d G . . . .
H29A H -0.063455 0.698643 -0.013415 0.081 Uiso 1 1 d G . . . .
O31 O 0.6570(5) 0.60981(18) -0.20452(15) 0.0417(6) Uani 1 1 d . . . . .
H31A H 0.667273 0.621003 -0.152296 0.063 Uiso 1 1 d G . . . .
H31B H 0.821357 0.632298 -0.224101 0.063 Uiso 1 1 d G . . . .
O32 O 1.1555(6) 0.67842(18) -0.27822(18) 0.0466(6) Uani 1 1 d . . . . .
H32A H 1.192903 0.731784 -0.299203 0.070 Uiso 1 1 d G . . . .
H32B H 1.321734 0.662618 -0.254204 0.070 Uiso 1 1 d G . . . .


_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
N1 C2 1.337(5) . ?
N1 C6 1.339(5) . ?
C2 H2 0.96(4) . ?
C2 C3 1.380(5) . ?
C3 H3 0.9500 . ?
C3 C4 1.384(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.391(5) . ?
C5 C6 1.385(5) . ?
C5 C7 1.506(5) . ?
C6 H6 0.9500 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 N8 1.482(4) . ?
N8 C9 1.393(4) . ?
N8 C18 1.398(4) . ?
C9 O10 1.230(4) . ?
C9 C11 1.469(5) . ?
C11 C12 1.387(5) . ?
C11 C16 1.410(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.396(5) . ?
C13 H13 0.9500 . ?
C13 C14 1.376(5) . ?
C14 H14 0.9500 . ?
C14 C15 1.419(5) . ?
C15 C16 1.418(5) . ?
C15 C22 1.443(4) . ?
C16 C17 1.420(4) . ?
C17 C18 1.456(5) . ?
C17 C20 1.379(5) . ?
C18 O19 1.235(4) . ?
C20 H20 0.9500 . ?
C20 C21 1.390(5) . ?
C21 H21 0.9500 . ?
C21 C22 1.383(5) . ?
C22 N23 1.410(4) . ?
N23 C24 1.483(4) . ?
N23 C28 1.474(4) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C24 C25 1.504(5) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C25 O26 1.429(4) . ?
O26 C27 1.429(4) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C27 C28 1.513(5) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
O30 H30A 0.8698 . ?
O30 H30B 0.8703 . ?
O29 H29B 0.8698 . ?
O29 H29A 0.8703 . ?
O31 H31A 0.8697 . ?
O31 H31B 0.8692 . ?
O32 H32A 0.8704 . ?
O32 H32B 0.8700 . ?

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 N1 C6 117.6(3) . . ?
N1 C2 H2 115(2) . . ?
N1 C2 C3 123.2(3) . . ?
C3 C2 H2 121(2) . . ?
C2 C3 H3 120.8 . . ?
C2 C3 C4 118.3(3) . . ?
C4 C3 H3 120.8 . . ?
C3 C4 H4 120.2 . . ?
C3 C4 C5 119.7(3) . . ?
C5 C4 H4 120.2 . . ?
C4 C5 C7 122.1(3) . . ?
C6 C5 C4 117.4(3) . . ?
C6 C5 C7 120.5(3) . . ?
N1 C6 C5 123.7(3) . . ?
N1 C6 H6 118.1 . . ?
C5 C6 H6 118.1 . . ?
C5 C7 H7A 109.1 . . ?
C5 C7 H7B 109.1 . . ?
H7A C7 H7B 107.9 . . ?
N8 C7 C5 112.4(3) . . ?
N8 C7 H7A 109.1 . . ?
N8 C7 H7B 109.1 . . ?
C9 N8 C7 117.0(3) . . ?
C9 N8 C18 124.5(3) . . ?
C18 N8 C7 118.5(3) . . ?
N8 C9 C11 117.3(3) . . ?
O10 C9 N8 119.3(3) . . ?
O10 C9 C11 123.4(3) . . ?
C12 C11 C9 119.6(3) . . ?
C12 C11 C16 120.0(3) . . ?
C16 C11 C9 120.4(3) . . ?
C11 C12 H12 119.9 . . ?
C11 C12 C13 120.3(3) . . ?
C13 C12 H12 119.9 . . ?
C12 C13 H13 119.7 . . ?
C14 C13 C12 120.6(3) . . ?
C14 C13 H13 119.7 . . ?
C13 C14 H14 119.6 . . ?
C13 C14 C15 120.8(3) . . ?
C15 C14 H14 119.6 . . ?
C14 C15 C22 122.8(3) . . ?
C16 C15 C14 118.2(3) . . ?
C16 C15 C22 118.9(3) . . ?
C11 C16 C15 120.0(3) . . ?
C11 C16 C17 119.7(3) . . ?
C15 C16 C17 120.3(3) . . ?
C16 C17 C18 120.7(3) . . ?
C20 C17 C16 119.0(3) . . ?
C20 C17 C18 120.3(3) . . ?
N8 C18 C17 117.2(3) . . ?
O19 C18 N8 119.4(3) . . ?
O19 C18 C17 123.4(3) . . ?
C17 C20 H20 119.3 . . ?
C17 C20 C21 121.3(3) . . ?
C21 C20 H20 119.3 . . ?
C20 C21 H21 119.2 . . ?
C22 C21 C20 121.6(3) . . ?
C22 C21 H21 119.2 . . ?
C21 C22 C15 118.6(3) . . ?
C21 C22 N23 123.1(3) . . ?
N23 C22 C15 118.3(3) . . ?
C22 N23 C24 114.0(2) . . ?
C22 N23 C28 115.2(3) . . ?
C28 N23 C24 109.1(3) . . ?
N23 C24 H24A 109.5 . . ?
N23 C24 H24B 109.5 . . ?
N23 C24 C25 110.7(3) . . ?
H24A C24 H24B 108.1 . . ?
C25 C24 H24A 109.5 . . ?
C25 C24 H24B 109.5 . . ?
C24 C25 H25A 109.4 . . ?
C24 C25 H25B 109.4 . . ?
H25A C25 H25B 108.0 . . ?
O26 C25 C24 111.3(3) . . ?
O26 C25 H25A 109.4 . . ?
O26 C25 H25B 109.4 . . ?
C25 O26 C27 109.7(3) . . ?
O26 C27 H27A 109.4 . . ?
O26 C27 H27B 109.4 . . ?
O26 C27 C28 111.2(3) . . ?
H27A C27 H27B 108.0 . . ?
C28 C27 H27A 109.4 . . ?
C28 C27 H27B 109.4 . . ?
N23 C28 C27 108.9(3) . . ?
N23 C28 H28A 109.9 . . ?
N23 C28 H28B 109.9 . . ?
C27 C28 H28A 109.9 . . ?
C27 C28 H28B 109.9 . . ?
H28A C28 H28B 108.3 . . ?
H30A O30 H30B 104.5 . . ?
H29B O29 H29A 109.5 . . ?
H31A O31 H31B 104.5 . . ?
H32A O32 H32B 104.5 . . ?

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
N1 C2 C3 C4 0.2(5) . . . . ?
C2 N1 C6 C5 -0.3(5) . . . . ?
C2 C3 C4 C5 -0.7(5) . . . . ?
C3 C4 C5 C6 0.7(5) . . . . ?
C3 C4 C5 C7 179.2(3) . . . . ?
C4 C5 C6 N1 -0.2(5) . . . . ?
C4 C5 C7 N8 55.5(4) . . . . ?
C5 C7 N8 C9 81.0(3) . . . . ?
C5 C7 N8 C18 -98.2(3) . . . . ?
C6 N1 C2 C3 0.2(5) . . . . ?
C6 C5 C7 N8 -126.0(3) . . . . ?
C7 C5 C6 N1 -178.8(3) . . . . ?
C7 N8 C9 O10 -0.9(4) . . . . ?
C7 N8 C9 C11 178.4(3) . . . . ?
C7 N8 C18 C17 -179.9(3) . . . . ?
C7 N8 C18 O19 -0.6(4) . . . . ?
N8 C9 C11 C12 -178.9(3) . . . . ?
N8 C9 C11 C16 0.9(4) . . . . ?
C9 N8 C18 C17 1.0(4) . . . . ?
C9 N8 C18 O19 -179.8(3) . . . . ?
C9 C11 C12 C13 -179.4(3) . . . . ?
C9 C11 C16 C15 -178.5(3) . . . . ?
C9 C11 C16 C17 2.0(4) . . . . ?
O10 C9 C11 C12 0.4(5) . . . . ?
O10 C9 C11 C16 -179.8(3) . . . . ?
C11 C12 C13 C14 -1.4(5) . . . . ?
C11 C16 C17 C18 -3.5(4) . . . . ?
C11 C16 C17 C20 177.0(3) . . . . ?
C12 C11 C16 C15 1.4(4) . . . . ?
C12 C11 C16 C17 -178.2(3) . . . . ?
C12 C13 C14 C15 0.0(5) . . . . ?
C13 C14 C15 C16 2.1(4) . . . . ?
C13 C14 C15 C22 180.0(3) . . . . ?
C14 C15 C16 C11 -2.7(4) . . . . ?
C14 C15 C16 C17 176.8(3) . . . . ?
C14 C15 C22 C21 -173.4(3) . . . . ?
C14 C15 C22 N23 6.7(4) . . . . ?
C15 C16 C17 C18 177.0(3) . . . . ?
C15 C16 C17 C20 -2.6(4) . . . . ?
C15 C22 N23 C24 70.5(4) . . . . ?
C15 C22 N23 C28 -162.3(3) . . . . ?
C16 C11 C12 C13 0.7(5) . . . . ?
C16 C15 C22 C21 4.5(4) . . . . ?
C16 C15 C22 N23 -175.4(3) . . . . ?
C16 C17 C18 N8 2.1(4) . . . . ?
C16 C17 C18 O19 -177.2(3) . . . . ?
C16 C17 C20 C21 3.0(5) . . . . ?
C17 C20 C21 C22 0.4(5) . . . . ?
C18 N8 C9 O10 178.3(3) . . . . ?
C18 N8 C9 C11 -2.4(4) . . . . ?
C18 C17 C20 C21 -176.5(3) . . . . ?
C20 C17 C18 N8 -178.4(3) . . . . ?
C20 C17 C18 O19 2.3(5) . . . . ?
C20 C21 C22 C15 -4.2(5) . . . . ?
C20 C21 C22 N23 175.7(3) . . . . ?
C21 C22 N23 C24 -109.4(3) . . . . ?
C21 C22 N23 C28 17.8(4) . . . . ?
C22 C15 C16 C11 179.3(3) . . . . ?
C22 C15 C16 C17 -1.2(4) . . . . ?
C22 N23 C24 C25 -173.6(3) . . . . ?
C22 N23 C28 C27 173.2(3) . . . . ?
N23 C24 C25 O26 -57.0(4) . . . . ?
C24 N23 C28 C27 -57.1(4) . . . . ?
C24 C25 O26 C27 58.4(4) . . . . ?
C25 O26 C27 C28 -60.5(4) . . . . ?
O26 C27 C28 N23 60.5(4) . . . . ?
C28 N23 C24 C25 56.1(3) . . . . ?

_olex2_exptl_crystal_mounting_method 'mounted in oil on a MiTeGen microloop'
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_L2a
_database_code_depnum_ccdc_archive 'CCDC 2048286'
loop_
_audit_author_name
_audit_author_address
'June  Lovitt'
;Trinity College Dublin
Republic of Ireland
;
_audit_update_record             
;
2020-12-04 deposited with the CCDC.	2021-03-15 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_RINTA01_L2a                 
;
PROBLEM: The value of Rint is greater than 0.18
RESPONSE: Compound L2a exhibited poor diffraction characteristics with generally low intensity scattering. Only a low resolution dataset could be obtained.
;
_vrf_PLAT020_L2a                 
;
PROBLEM: The Value of Rint is Greater Than 0.12 .........      0.212 Report
RESPONSE: Compound L2a exhibited poor diffraction characteristics with generally low intensity scattering. Only a low resolution dataset could be obtained.
;
# Added during the CSD deposition process: Friday 04 December 2020 10:22 AM
# end Validation Reply Form


###### original file name data_data_jil056
_audit_creation_date             2020-11-26
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2016/4
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H12 N2 O4'
_chemical_formula_sum            'C19 H12 N2 O4'
_chemical_formula_weight         332.31
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   6.9839(7)
_cell_length_b                   17.9787(19)
_cell_length_c                   23.148(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2906.5(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3258
_cell_measurement_temperature    100.01
_cell_measurement_theta_max      25.47
_cell_measurement_theta_min      2.87
_shelx_estimated_absorpt_T_max   0.995
_shelx_estimated_absorpt_T_min   0.955
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6183
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0898 before and 0.0749 after correction.
The Ratio of minimum to maximum transmission is 0.8295.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.519
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             1376
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1.00 0.00 -1.00 0.0190
0.00 0.00 -1.00 0.0160
0.00 0.00 1.00 0.0200
0.00 -4.00 -3.00 0.2040
0.00 3.00 2.00 0.1850
-2.00 0.00 -3.00 0.0110
-1.00 0.00 0.00 0.0140
-4.00 -1.00 4.00 0.1040

_exptl_crystal_size_max          0.427
_exptl_crystal_size_mid          0.077
_exptl_crystal_size_min          0.046
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.2123
_diffrn_reflns_av_unetI/netI     0.0776
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            36980
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.426
_diffrn_reflns_theta_min         2.431
_diffrn_ambient_temperature      100.01
_diffrn_detector                 'CMOS area detector'
_diffrn_detector_area_resol_mean 5.12
_diffrn_detector_type            'Bruker PHOTON 50'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_collimation    '0.5 mm double-pinhole'
_diffrn_radiation_detector       'Bruker PHOTON 50'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           20.0
_diffrn_source_power             1.0
_diffrn_source_type              'Siemens, KFF Mo 2K -90 C'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1561
_reflns_number_total             2990
_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       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       'APEX 3 (Bruker, 2017) '
_computing_data_reduction        'SAINT V8.38A (Bruker, 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 2016/4 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.414
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         2990
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1678
_refine_ls_R_factor_gt           0.0827
_refine_ls_restrained_S_all      1.054
_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)+(0.0821P)²+3.6179P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1733
_refine_ls_wR_factor_ref         0.2147
_refine_special_details          
;
Poor diffraction characteristics with generally low intensity scattering. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
2.b Aromatic/amide H refined with riding coordinates:
 C13(H13), C21(H21), C22(H22), C12(H12), C23(H23), C8(H8), C6(H6), C7(H7),
 C4(H4), C5(H5)
;
_atom_sites_solution_hydrogens   geom
_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
O25 O 0.0624(4) 0.66577(16) 0.30810(15) 0.0494(9) Uani 1 1 d . . . . .
O17 O 0.0673(5) 0.31117(17) 0.12994(14) 0.0478(8) Uani 1 1 d . . . . .
O10 O 0.0872(5) 0.45889(18) 0.42042(16) 0.0521(9) Uani 1 1 d . . . . .
O16 O 0.2966(4) 0.25162(18) 0.17494(16) 0.0541(9) Uani 1 1 d . . . . .
N1 N 0.0698(5) 0.56286(18) 0.36474(17) 0.0373(9) Uani 1 1 d . . . . .
N15 N 0.1756(5) 0.3014(2) 0.17221(19) 0.0441(10) Uani 1 1 d . . . . .
C19 C 0.1070(5) 0.4727(2) 0.2639(2) 0.0333(10) Uani 1 1 d . . . . .
C9 C 0.0914(6) 0.4862(2) 0.3719(2) 0.0401(11) Uani 1 1 d . . . . .
C20 C 0.0815(5) 0.5510(2) 0.2589(2) 0.0343(10) Uani 1 1 d . . . . .
C18 C 0.1246(5) 0.4292(2) 0.2128(2) 0.0351(11) Uani 1 1 d . . . . .
C13 C 0.1768(5) 0.3211(2) 0.2753(2) 0.0399(12) Uani 1 1 d . . . . .
H13 H 0.205352 0.269690 0.279078 0.048 Uiso 1 1 calc R U . . .
C24 C 0.0708(5) 0.5980(2) 0.3110(2) 0.0382(11) Uani 1 1 d . . . . .
C21 C 0.0721(5) 0.5834(2) 0.2050(2) 0.0381(11) Uani 1 1 d . . . . .
H21 H 0.053557 0.635577 0.201706 0.046 Uiso 1 1 calc R U . . .
C11 C 0.1171(5) 0.4405(2) 0.3194(2) 0.0352(11) Uani 1 1 d . . . . .
C14 C 0.1595(5) 0.3519(2) 0.2223(2) 0.0361(11) Uani 1 1 d . . . . .
C22 C 0.0897(6) 0.5403(2) 0.1553(2) 0.0418(11) Uani 1 1 d . . . . .
H22 H 0.083791 0.563720 0.118578 0.050 Uiso 1 1 calc R U . . .
C12 C 0.1526(5) 0.3654(2) 0.3252(2) 0.0394(11) Uani 1 1 d . . . . .
H12 H 0.160690 0.343529 0.362456 0.047 Uiso 1 1 calc R U . . .
C23 C 0.1154(5) 0.4650(2) 0.1583(2) 0.0387(11) Uani 1 1 d . . . . .
H23 H 0.127135 0.436686 0.123887 0.046 Uiso 1 1 calc R U . . .
C3 C 0.2390(6) 0.6304(2) 0.4430(2) 0.0409(11) Uani 1 1 d . . . . .
C2 C 0.0485(6) 0.6086(3) 0.4177(2) 0.0453(12) Uani 1 1 d . . . . .
H2A H -0.025118 0.580175 0.446805 0.054 Uiso 1 1 calc R U . . .
H2B H -0.024944 0.654110 0.408278 0.054 Uiso 1 1 calc R U . . .
C8 C 0.3326(7) 0.6930(3) 0.4244(2) 0.0514(13) Uani 1 1 d . . . . .
H8 H 0.275706 0.723741 0.395756 0.062 Uiso 1 1 calc R U . . .
C6 C 0.5980(7) 0.6673(3) 0.4879(2) 0.0557(14) Uani 1 1 d . . . . .
H6 H 0.721438 0.679382 0.502404 0.067 Uiso 1 1 calc R U . . .
C7 C 0.5116(8) 0.7118(3) 0.4473(2) 0.0586(15) Uani 1 1 d . . . . .
H7 H 0.574021 0.755879 0.434733 0.070 Uiso 1 1 calc R U . . .
C4 C 0.3253(8) 0.5877(3) 0.4855(2) 0.0560(14) Uani 1 1 d . . . . .
H4 H 0.259920 0.545377 0.500049 0.067 Uiso 1 1 calc R U . . .
C5 C 0.5038(8) 0.6052(3) 0.5072(2) 0.0637(16) Uani 1 1 d . . . . .
H5 H 0.561302 0.574222 0.535567 0.076 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
O25 C24 1.222(5) . ?
O17 N15 1.249(5) . ?
O10 C9 1.226(5) . ?
O16 N15 1.233(5) . ?
N1 C9 1.396(5) . ?
N1 C24 1.395(6) . ?
N1 C2 1.483(6) . ?
N15 C14 1.477(6) . ?
C19 C20 1.423(5) . ?
C19 C18 1.423(6) . ?
C19 C11 1.412(6) . ?
C9 C11 1.478(6) . ?
C20 C24 1.475(6) . ?
C20 C21 1.379(6) . ?
C18 C14 1.429(6) . ?
C18 C23 1.417(6) . ?
C13 H13 0.9500 . ?
C13 C14 1.351(6) . ?
C13 C12 1.411(6) . ?
C21 H21 0.9500 . ?
C21 C22 1.391(6) . ?
C11 C12 1.380(6) . ?
C22 H22 0.9500 . ?
C22 C23 1.368(6) . ?
C12 H12 0.9500 . ?
C23 H23 0.9500 . ?
C3 C2 1.505(6) . ?
C3 C8 1.371(6) . ?
C3 C4 1.385(7) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C8 H8 0.9500 . ?
C8 C7 1.400(7) . ?
C6 H6 0.9500 . ?
C6 C7 1.374(7) . ?
C6 C5 1.371(8) . ?
C7 H7 0.9500 . ?
C4 H4 0.9500 . ?
C4 C5 1.381(7) . ?
C5 H5 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
C9 N1 C2 117.4(4) . . ?
C24 N1 C9 123.5(4) . . ?
C24 N1 C2 119.1(4) . . ?
O17 N15 C14 118.9(4) . . ?
O16 N15 O17 123.9(4) . . ?
O16 N15 C14 117.2(4) . . ?
C18 C19 C20 119.2(4) . . ?
C11 C19 C20 119.1(4) . . ?
C11 C19 C18 121.8(4) . . ?
O10 C9 N1 120.1(5) . . ?
O10 C9 C11 122.2(4) . . ?
N1 C9 C11 117.7(4) . . ?
C19 C20 C24 120.4(4) . . ?
C21 C20 C19 119.8(4) . . ?
C21 C20 C24 119.8(4) . . ?
C19 C18 C14 114.9(4) . . ?
C23 C18 C19 119.0(4) . . ?
C23 C18 C14 126.0(4) . . ?
C14 C13 H13 120.0 . . ?
C14 C13 C12 120.1(4) . . ?
C12 C13 H13 120.0 . . ?
O25 C24 N1 120.1(4) . . ?
O25 C24 C20 121.9(4) . . ?
N1 C24 C20 118.0(4) . . ?
C20 C21 H21 119.7 . . ?
C20 C21 C22 120.6(4) . . ?
C22 C21 H21 119.7 . . ?
C19 C11 C9 121.0(4) . . ?
C12 C11 C19 119.9(4) . . ?
C12 C11 C9 119.1(4) . . ?
C18 C14 N15 119.3(4) . . ?
C13 C14 N15 117.1(4) . . ?
C13 C14 C18 123.6(4) . . ?
C21 C22 H22 119.3 . . ?
C23 C22 C21 121.4(5) . . ?
C23 C22 H22 119.3 . . ?
C13 C12 H12 120.2 . . ?
C11 C12 C13 119.6(5) . . ?
C11 C12 H12 120.2 . . ?
C18 C23 H23 120.0 . . ?
C22 C23 C18 120.1(5) . . ?
C22 C23 H23 120.0 . . ?
C8 C3 C2 120.9(5) . . ?
C8 C3 C4 118.0(5) . . ?
C4 C3 C2 121.1(4) . . ?
N1 C2 C3 112.1(3) . . ?
N1 C2 H2A 109.2 . . ?
N1 C2 H2B 109.2 . . ?
C3 C2 H2A 109.2 . . ?
C3 C2 H2B 109.2 . . ?
H2A C2 H2B 107.9 . . ?
C3 C8 H8 119.8 . . ?
C3 C8 C7 120.3(5) . . ?
C7 C8 H8 119.8 . . ?
C7 C6 H6 120.4 . . ?
C5 C6 H6 120.4 . . ?
C5 C6 C7 119.1(5) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 C8 120.7(5) . . ?
C6 C7 H7 119.6 . . ?
C3 C4 H4 119.1 . . ?
C5 C4 C3 121.7(5) . . ?
C5 C4 H4 119.1 . . ?
C6 C5 C4 120.0(6) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?

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
O17 N15 C14 C18 -38.5(5) . . . . ?
O17 N15 C14 C13 140.7(4) . . . . ?
O10 C9 C11 C19 175.2(4) . . . . ?
O10 C9 C11 C12 -5.2(6) . . . . ?
O16 N15 C14 C18 141.6(4) . . . . ?
O16 N15 C14 C13 -39.2(5) . . . . ?
N1 C9 C11 C19 -4.2(5) . . . . ?
N1 C9 C11 C12 175.4(3) . . . . ?
C19 C20 C24 O25 174.8(4) . . . . ?
C19 C20 C24 N1 -5.4(5) . . . . ?
C19 C20 C21 C22 -0.8(6) . . . . ?
C19 C18 C14 N15 178.6(3) . . . . ?
C19 C18 C14 C13 -0.6(5) . . . . ?
C19 C18 C23 C22 -0.1(5) . . . . ?
C19 C11 C12 C13 -0.6(5) . . . . ?
C9 N1 C24 O25 -175.7(4) . . . . ?
C9 N1 C24 C20 4.5(5) . . . . ?
C9 N1 C2 C3 85.9(5) . . . . ?
C9 C11 C12 C13 179.8(3) . . . . ?
C20 C19 C18 C14 176.9(3) . . . . ?
C20 C19 C18 C23 -0.2(5) . . . . ?
C20 C19 C11 C9 3.3(5) . . . . ?
C20 C19 C11 C12 -176.4(3) . . . . ?
C20 C21 C22 C23 0.4(6) . . . . ?
C18 C19 C20 C24 -177.5(3) . . . . ?
C18 C19 C20 C21 0.7(5) . . . . ?
C18 C19 C11 C9 -177.7(3) . . . . ?
C18 C19 C11 C12 2.7(5) . . . . ?
C24 N1 C9 O10 -179.2(4) . . . . ?
C24 N1 C9 C11 0.2(5) . . . . ?
C24 N1 C2 C3 -92.9(5) . . . . ?
C24 C20 C21 C22 177.4(4) . . . . ?
C21 C20 C24 O25 -3.4(6) . . . . ?
C21 C20 C24 N1 176.4(4) . . . . ?
C21 C22 C23 C18 0.0(6) . . . . ?
C11 C19 C20 C24 1.6(5) . . . . ?
C11 C19 C20 C21 179.7(3) . . . . ?
C11 C19 C18 C14 -2.1(5) . . . . ?
C11 C19 C18 C23 -179.3(3) . . . . ?
C14 C18 C23 C22 -176.9(4) . . . . ?
C14 C13 C12 C11 -2.0(6) . . . . ?
C12 C13 C14 N15 -176.5(3) . . . . ?
C12 C13 C14 C18 2.6(6) . . . . ?
C23 C18 C14 N15 -4.5(6) . . . . ?
C23 C18 C14 C13 176.4(4) . . . . ?
C3 C8 C7 C6 1.3(7) . . . . ?
C3 C4 C5 C6 1.8(8) . . . . ?
C2 N1 C9 O10 2.0(6) . . . . ?
C2 N1 C9 C11 -178.6(3) . . . . ?
C2 N1 C24 O25 3.1(5) . . . . ?
C2 N1 C24 C20 -176.7(3) . . . . ?
C2 C3 C8 C7 -178.6(4) . . . . ?
C2 C3 C4 C5 177.1(5) . . . . ?
C8 C3 C2 N1 86.7(5) . . . . ?
C8 C3 C4 C5 -2.7(7) . . . . ?
C7 C6 C5 C4 0.6(8) . . . . ?
C4 C3 C2 N1 -93.0(5) . . . . ?
C4 C3 C8 C7 1.1(7) . . . . ?
C5 C6 C7 C8 -2.2(8) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_L2
_database_code_depnum_ccdc_archive 'CCDC 2048287'
loop_
_audit_author_name
_audit_author_address
'June  Lovitt'
;Trinity College Dublin
Republic of Ireland
;
_audit_update_record             
;
2020-12-04 deposited with the CCDC.	2021-03-15 downloaded from the CCDC.
;
###### original file name data_jil055_0m
_audit_creation_date             2020-11-26
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2016/4
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H20 N2 O3'
_chemical_formula_sum            'C23 H20 N2 O3'
_chemical_formula_weight         372.41
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   15.4559(16)
_cell_length_b                   7.0602(7)
_cell_length_c                   17.1898(17)
_cell_angle_alpha                90
_cell_angle_beta                 111.632(3)
_cell_angle_gamma                90
_cell_volume                     1743.7(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4711
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      27.55
_cell_measurement_theta_min      2.83
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6568
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0761 before and 0.0644 after correction.
The Ratio of minimum to maximum transmission is 0.8809.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0791
_diffrn_reflns_av_unetI/netI     0.0499
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            24037
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.566
_diffrn_reflns_theta_min         2.835
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           20.0
_diffrn_source_power             1.0
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2668
_reflns_number_total             4016
_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       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 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 2016/4 (Sheldrick, 2015)'
_computing_structure_solution    'XT  (Sheldrick, 2015)'
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         4016
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0888
_refine_ls_R_factor_gt           0.0494
_refine_ls_restrained_S_all      1.016
_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)+(0.0567P)²+0.5967P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1058
_refine_ls_wR_factor_ref         0.1236
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C27(H27A,H27B)
;
_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
O19 O 0.68589(9) 0.31080(18) 0.47062(8) 0.0236(3) Uani 1 1 d . . . . .
O10 O 0.74798(9) 0.10415(19) 0.73545(9) 0.0256(3) Uani 1 1 d . . . . .
O26 O 0.11740(10) 0.1233(2) 0.60498(9) 0.0321(4) Uani 1 1 d . . . . .
N8 N 0.71628(10) 0.2037(2) 0.60184(10) 0.0180(3) Uani 1 1 d . . . . .
N23 N 0.30044(11) 0.1142(2) 0.60354(10) 0.0194(3) Uani 1 1 d . . . . .
C15 C 0.42638(12) 0.1945(2) 0.55604(11) 0.0172(4) Uani 1 1 d . . . . .
C16 C 0.52380(13) 0.2042(2) 0.57265(11) 0.0168(4) Uani 1 1 d . . . . .
C4 C 0.86590(13) 0.3780(3) 0.63375(11) 0.0186(4) Uani 1 1 d . . . . .
C13 C 0.46234(13) 0.0749(3) 0.69674(12) 0.0204(4) Uani 1 1 d . . . . .
C17 C 0.55478(13) 0.2580(2) 0.50819(12) 0.0175(4) Uani 1 1 d . . . . .
C11 C 0.58900(13) 0.1517(2) 0.65198(11) 0.0179(4) Uani 1 1 d . . . . .
C9 C 0.68920(13) 0.1502(2) 0.66818(12) 0.0190(4) Uani 1 1 d . . . . .
C12 C 0.55761(13) 0.0873(3) 0.71251(12) 0.0203(4) Uani 1 1 d . . . . .
C22 C 0.36472(14) 0.2335(2) 0.47366(12) 0.0190(4) Uani 1 1 d . . . . .
C14 C 0.39636(13) 0.1302(2) 0.62097(12) 0.0183(4) Uani 1 1 d . . . . .
C18 C 0.65539(13) 0.2623(2) 0.52361(12) 0.0186(4) Uani 1 1 d . . . . .
C3 C 0.83709(14) 0.5232(3) 0.67299(12) 0.0207(4) Uani 1 1 d . . . . .
C21 C 0.39670(13) 0.2844(3) 0.41240(12) 0.0205(4) Uani 1 1 d . . . . .
C2 C 0.88839(14) 0.6895(3) 0.69617(13) 0.0239(4) Uani 1 1 d . . . . .
C5 C 0.94772(14) 0.4003(3) 0.61879(13) 0.0250(4) Uani 1 1 d . . . . .
C7 C 0.81536(13) 0.1909(3) 0.61407(14) 0.0216(4) Uani 1 1 d . . . . .
C24 C 0.27246(14) -0.0144(3) 0.65659(13) 0.0223(4) Uani 1 1 d . . . . .
C20 C 0.49261(14) 0.2992(2) 0.42962(12) 0.0203(4) Uani 1 1 d . . . . .
C1 C 0.96893(14) 0.7113(3) 0.68042(13) 0.0269(5) Uani 1 1 d . . . . .
C28 C 0.24727(14) 0.2927(3) 0.59137(14) 0.0249(4) Uani 1 1 d . . . . .
C6 C 0.99896(15) 0.5660(3) 0.64269(14) 0.0293(5) Uani 1 1 d . . . . .
C25 C 0.16905(15) -0.0487(3) 0.61825(14) 0.0270(5) Uani 1 1 d . . . . .
C27 C 0.14478(15) 0.2479(3) 0.55305(14) 0.0307(5) Uani 1 1 d . . . . .
H27A H 0.108573 0.366842 0.544721 0.037 Uiso 1 1 calc R U . . .
H27B H 0.130735 0.188405 0.497574 0.037 Uiso 1 1 calc R U . . .
H13 H 0.4428(14) 0.025(3) 0.7397(13) 0.020(5) Uiso 1 1 d . . . . .
H2 H 0.8690(14) 0.782(3) 0.7243(13) 0.022(5) Uiso 1 1 d . . . . .
H3 H 0.7803(15) 0.507(3) 0.6844(13) 0.026(6) Uiso 1 1 d . . . . .
H7A H 0.8433(14) 0.103(3) 0.6613(13) 0.022(5) Uiso 1 1 d . . . . .
H24A H 0.2894(14) 0.045(3) 0.7133(13) 0.021(5) Uiso 1 1 d . . . . .
H21 H 0.3530(14) 0.300(3) 0.3561(13) 0.020(5) Uiso 1 1 d . . . . .
H12 H 0.6023(15) 0.048(3) 0.7657(14) 0.030(6) Uiso 1 1 d . . . . .
H7B H 0.8177(13) 0.137(3) 0.5625(12) 0.013(5) Uiso 1 1 d . . . . .
H24B H 0.3062(15) -0.137(3) 0.6614(13) 0.025(6) Uiso 1 1 d . . . . .
H20 H 0.5173(14) 0.333(3) 0.3879(13) 0.019(5) Uiso 1 1 d . . . . .
H1 H 1.0019(16) 0.827(3) 0.6960(14) 0.034(6) Uiso 1 1 d . . . . .
H25A H 0.1489(16) -0.131(3) 0.6562(15) 0.038(6) Uiso 1 1 d . . . . .
H28A H 0.2604(15) 0.354(3) 0.6456(15) 0.030(6) Uiso 1 1 d . . . . .
H22 H 0.2996(14) 0.221(3) 0.4611(12) 0.018(5) Uiso 1 1 d . . . . .
H5 H 0.9705(15) 0.299(3) 0.5912(14) 0.029(6) Uiso 1 1 d . . . . .
H25B H 0.1534(15) -0.115(3) 0.5619(15) 0.030(6) Uiso 1 1 d . . . . .
H6 H 1.0566(18) 0.581(4) 0.6301(16) 0.047(7) Uiso 1 1 d . . . . .
H28B H 0.2664(16) 0.380(3) 0.5555(14) 0.032(6) 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
O19 C18 1.219(2) . ?
O10 C9 1.222(2) . ?
O26 C25 1.425(3) . ?
O26 C27 1.424(2) . ?
N8 C9 1.404(2) . ?
N8 C18 1.390(2) . ?
N8 C7 1.470(2) . ?
N23 C14 1.405(2) . ?
N23 C24 1.461(2) . ?
N23 C28 1.476(2) . ?
C15 C16 1.427(2) . ?
C15 C22 1.412(3) . ?
C15 C14 1.431(2) . ?
C16 C17 1.412(2) . ?
C16 C11 1.414(3) . ?
C4 C3 1.388(3) . ?
C4 C5 1.389(3) . ?
C4 C7 1.508(3) . ?
C13 C12 1.398(3) . ?
C13 C14 1.382(3) . ?
C13 H13 0.96(2) . ?
C17 C18 1.478(3) . ?
C17 C20 1.369(3) . ?
C11 C9 1.469(3) . ?
C11 C12 1.377(3) . ?
C12 H12 0.96(2) . ?
C22 C21 1.366(3) . ?
C22 H22 0.95(2) . ?
C3 C2 1.390(3) . ?
C3 H3 0.97(2) . ?
C21 C20 1.404(3) . ?
C21 H21 0.96(2) . ?
C2 C1 1.377(3) . ?
C2 H2 0.93(2) . ?
C5 C6 1.387(3) . ?
C5 H5 0.99(2) . ?
C7 H7A 0.98(2) . ?
C7 H7B 0.98(2) . ?
C24 C25 1.507(3) . ?
C24 H24A 1.00(2) . ?
C24 H24B 1.00(2) . ?
C20 H20 0.96(2) . ?
C1 C6 1.382(3) . ?
C1 H1 0.95(2) . ?
C28 C27 1.508(3) . ?
C28 H28A 0.98(2) . ?
C28 H28B 0.99(2) . ?
C6 H6 1.00(3) . ?
C25 H25A 1.00(2) . ?
C25 H25B 1.02(2) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?

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
C27 O26 C25 110.37(15) . . ?
C9 N8 C7 118.32(16) . . ?
C18 N8 C9 124.59(15) . . ?
C18 N8 C7 117.05(15) . . ?
C14 N23 C24 116.67(15) . . ?
C14 N23 C28 116.77(15) . . ?
C24 N23 C28 109.97(15) . . ?
C16 C15 C14 118.72(16) . . ?
C22 C15 C16 117.61(17) . . ?
C22 C15 C14 123.43(17) . . ?
C17 C16 C15 119.61(17) . . ?
C17 C16 C11 120.02(17) . . ?
C11 C16 C15 120.31(16) . . ?
C3 C4 C5 118.91(17) . . ?
C3 C4 C7 121.57(17) . . ?
C5 C4 C7 119.30(17) . . ?
C12 C13 H13 118.7(12) . . ?
C14 C13 C12 121.57(18) . . ?
C14 C13 H13 119.7(12) . . ?
C16 C17 C18 120.23(17) . . ?
C20 C17 C16 120.91(17) . . ?
C20 C17 C18 118.80(17) . . ?
C16 C11 C9 120.75(17) . . ?
C12 C11 C16 119.40(17) . . ?
C12 C11 C9 119.67(17) . . ?
O10 C9 N8 120.00(17) . . ?
O10 C9 C11 123.03(17) . . ?
N8 C9 C11 116.97(16) . . ?
C13 C12 H12 120.2(13) . . ?
C11 C12 C13 120.88(18) . . ?
C11 C12 H12 118.9(13) . . ?
C15 C22 H22 118.4(12) . . ?
C21 C22 C15 121.47(18) . . ?
C21 C22 H22 120.1(12) . . ?
N23 C14 C15 118.63(16) . . ?
C13 C14 N23 122.17(17) . . ?
C13 C14 C15 119.07(17) . . ?
O19 C18 N8 119.75(17) . . ?
O19 C18 C17 122.87(17) . . ?
N8 C18 C17 117.37(15) . . ?
C4 C3 C2 120.78(18) . . ?
C4 C3 H3 118.9(13) . . ?
C2 C3 H3 120.3(12) . . ?
C22 C21 C20 120.72(18) . . ?
C22 C21 H21 119.1(12) . . ?
C20 C21 H21 120.0(12) . . ?
C3 C2 H2 119.1(13) . . ?
C1 C2 C3 119.97(19) . . ?
C1 C2 H2 120.9(13) . . ?
C4 C5 H5 121.0(12) . . ?
C6 C5 C4 120.01(19) . . ?
C6 C5 H5 119.0(12) . . ?
N8 C7 C4 113.86(15) . . ?
N8 C7 H7A 105.9(12) . . ?
N8 C7 H7B 106.2(11) . . ?
C4 C7 H7A 109.4(12) . . ?
C4 C7 H7B 110.9(11) . . ?
H7A C7 H7B 110.5(16) . . ?
N23 C24 C25 109.70(17) . . ?
N23 C24 H24A 108.3(12) . . ?
N23 C24 H24B 109.0(12) . . ?
C25 C24 H24A 110.3(12) . . ?
C25 C24 H24B 109.6(12) . . ?
H24A C24 H24B 110.0(17) . . ?
C17 C20 C21 119.63(18) . . ?
C17 C20 H20 117.6(12) . . ?
C21 C20 H20 122.8(12) . . ?
C2 C1 C6 119.59(19) . . ?
C2 C1 H1 118.1(14) . . ?
C6 C1 H1 122.3(14) . . ?
N23 C28 C27 108.84(16) . . ?
N23 C28 H28A 109.4(13) . . ?
N23 C28 H28B 109.9(13) . . ?
C27 C28 H28A 108.9(13) . . ?
C27 C28 H28B 111.4(13) . . ?
H28A C28 H28B 108.3(18) . . ?
C5 C6 H6 119.0(15) . . ?
C1 C6 C5 120.72(19) . . ?
C1 C6 H6 120.2(15) . . ?
O26 C25 C24 112.00(17) . . ?
O26 C25 H25A 107.8(13) . . ?
O26 C25 H25B 108.6(12) . . ?
C24 C25 H25A 110.0(14) . . ?
C24 C25 H25B 109.3(12) . . ?
H25A C25 H25B 109.1(18) . . ?
O26 C27 C28 111.27(18) . . ?
O26 C27 H27A 109.4 . . ?
O26 C27 H27B 109.4 . . ?
C28 C27 H27A 109.4 . . ?
C28 C27 H27B 109.4 . . ?
H27A C27 H27B 108.0 . . ?

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
N23 C24 C25 O26 -56.7(2) . . . . ?
N23 C28 C27 O26 59.0(2) . . . . ?
C15 C16 C17 C18 -177.88(15) . . . . ?
C15 C16 C17 C20 -0.7(2) . . . . ?
C15 C16 C11 C9 176.33(16) . . . . ?
C15 C16 C11 C12 1.3(3) . . . . ?
C15 C22 C21 C20 0.1(3) . . . . ?
C16 C15 C22 C21 -1.9(3) . . . . ?
C16 C15 C14 N23 -177.73(15) . . . . ?
C16 C15 C14 C13 -1.7(3) . . . . ?
C16 C17 C18 O19 -178.70(16) . . . . ?
C16 C17 C18 N8 2.8(2) . . . . ?
C16 C17 C20 C21 -1.2(3) . . . . ?
C16 C11 C9 O10 -179.27(17) . . . . ?
C16 C11 C9 N8 0.2(2) . . . . ?
C16 C11 C12 C13 -0.5(3) . . . . ?
C4 C3 C2 C1 -0.2(3) . . . . ?
C4 C5 C6 C1 -0.9(3) . . . . ?
C17 C16 C11 C9 -0.7(2) . . . . ?
C17 C16 C11 C12 -175.67(16) . . . . ?
C11 C16 C17 C18 -0.8(2) . . . . ?
C11 C16 C17 C20 176.35(16) . . . . ?
C9 N8 C18 O19 178.06(16) . . . . ?
C9 N8 C18 C17 -3.4(2) . . . . ?
C9 N8 C7 C4 -100.5(2) . . . . ?
C9 C11 C12 C13 -175.59(17) . . . . ?
C12 C13 C14 N23 178.44(17) . . . . ?
C12 C13 C14 C15 2.6(3) . . . . ?
C12 C11 C9 O10 -4.3(3) . . . . ?
C12 C11 C9 N8 175.22(16) . . . . ?
C22 C15 C16 C17 2.2(2) . . . . ?
C22 C15 C16 C11 -174.82(16) . . . . ?
C22 C15 C14 N23 -3.5(3) . . . . ?
C22 C15 C14 C13 172.56(17) . . . . ?
C22 C21 C20 C17 1.5(3) . . . . ?
C14 N23 C24 C25 -167.31(16) . . . . ?
C14 N23 C28 C27 166.23(17) . . . . ?
C14 C15 C16 C17 176.81(15) . . . . ?
C14 C15 C16 C11 -0.2(2) . . . . ?
C14 C15 C22 C21 -176.27(17) . . . . ?
C14 C13 C12 C11 -1.4(3) . . . . ?
C18 N8 C9 O10 -178.56(17) . . . . ?
C18 N8 C9 C11 1.9(2) . . . . ?
C18 N8 C7 C4 81.7(2) . . . . ?
C18 C17 C20 C21 176.06(16) . . . . ?
C3 C4 C5 C6 -0.3(3) . . . . ?
C3 C4 C7 N8 27.4(3) . . . . ?
C3 C2 C1 C6 -1.0(3) . . . . ?
C2 C1 C6 C5 1.5(3) . . . . ?
C5 C4 C3 C2 0.8(3) . . . . ?
C5 C4 C7 N8 -158.14(17) . . . . ?
C7 N8 C9 O10 3.8(2) . . . . ?
C7 N8 C9 C11 -175.75(15) . . . . ?
C7 N8 C18 O19 -4.3(2) . . . . ?
C7 N8 C18 C17 174.30(15) . . . . ?
C7 C4 C3 C2 175.25(18) . . . . ?
C7 C4 C5 C6 -174.85(19) . . . . ?
C24 N23 C14 C15 157.47(16) . . . . ?
C24 N23 C14 C13 -18.4(3) . . . . ?
C24 N23 C28 C27 -57.9(2) . . . . ?
C20 C17 C18 O19 4.0(3) . . . . ?
C20 C17 C18 N8 -174.46(15) . . . . ?
C28 N23 C14 C15 -69.6(2) . . . . ?
C28 N23 C14 C13 114.5(2) . . . . ?
C28 N23 C24 C25 56.7(2) . . . . ?
C25 O26 C27 C28 -58.7(2) . . . . ?
C27 O26 C25 C24 57.4(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'











####################################################################### 
# 
# 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_L1_gel
_database_code_depnum_ccdc_archive 'CCDC 2048285'
loop_
_audit_author_name
_audit_author_address
'June  Lovitt'
;Trinity College Dublin
Republic of Ireland
;
_audit_update_record             
;
2020-12-04 deposited with the CCDC.	2021-03-15 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_THETM01_L1_gel              
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: Compound L1_gel exhibited poor diffraction characteristics with generally low intensity scattering and no useful reflections beyond 0.95 Angstrom resolution. Only a low resolution dataset could be obtained.
;
# Added during the CSD deposition process: Friday 04 December 2020 10:22 AM
# end Validation Reply Form


###### original file name data_cu_jil082b_0m
_audit_creation_date             2020-11-26
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2016/4
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H19 N3 O3'
_chemical_formula_sum            'C22 H19 N3 O3'
_chemical_formula_weight         373.40
_chemical_melting_point          ?
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                   4.7218(5)
_cell_length_b                   11.9820(11)
_cell_length_c                   30.536(3)
_cell_angle_alpha                90
_cell_angle_beta                 92.951(7)
_cell_angle_gamma                90
_cell_volume                     1725.3(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1054
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      52.64
_cell_measurement_theta_min      2.90
_shelx_estimated_absorpt_T_max   0.977
_shelx_estimated_absorpt_T_min   0.939
_exptl_absorpt_coefficient_mu    0.793
_exptl_absorpt_correction_T_max  0.7507
_exptl_absorpt_correction_T_min  0.6585
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1290 before and 0.0766 after correction.
The Ratio of minimum to maximum transmission is 0.8772.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1082
_diffrn_reflns_av_unetI/netI     0.1205
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            11302
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        54.306
_diffrn_reflns_theta_max         54.306
_diffrn_reflns_theta_min         2.898
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           0.6
_diffrn_source_power             0.029796
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           49.66
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1358
_reflns_number_total             2094
_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       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 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 2016/4 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         2094
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1159
_refine_ls_R_factor_gt           0.0749
_refine_ls_restrained_S_all      1.075
_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)+4.1284P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1824
_refine_ls_wR_factor_ref         0.2058
_refine_special_details          
;
Poor diffraction characteristics with generally low intensity
scattering and no useful reflectons beyond 0.95 Angstrom.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C24(H24A,H24B), C25(H25A,H25B), C27(H27A,H27B), C28(H28A,H28B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C6(H6), C13(H13), C14(H14), C17(H17), C18(H18),
 C19(H19)
;
_atom_sites_solution_hydrogens   geom
_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
N1 N 1.0226(13) 0.4882(5) 0.92424(18) 0.0580(16) Uani 1 1 d . . . . .
C2 C 1.1608(15) 0.5507(7) 0.9545(2) 0.057(2) Uani 1 1 d . . . . .
H2 H 1.300062 0.515506 0.973370 0.069 Uiso 1 1 calc R U . . .
C3 C 1.1143(14) 0.6621(6) 0.9600(2) 0.0521(18) Uani 1 1 d . . . . .
H3 H 1.218886 0.702755 0.982090 0.062 Uiso 1 1 calc R U . . .
C4 C 0.9113(13) 0.7150(5) 0.93269(19) 0.0424(16) Uani 1 1 d . . . . .
H4 H 0.874205 0.792426 0.935990 0.051 Uiso 1 1 calc R U . . .
C5 C 0.7649(12) 0.6538(5) 0.90083(18) 0.0342(14) Uani 1 1 d . . . . .
C6 C 0.8301(14) 0.5413(5) 0.89810(19) 0.0438(17) Uani 1 1 d . . . . .
H6 H 0.730847 0.498672 0.876022 0.053 Uiso 1 1 calc R U . . .
C7 C 0.5429(12) 0.7061(5) 0.87013(18) 0.0350(15) Uani 1 1 d . . . . .
H7A H 0.360170 0.667135 0.873227 0.042 Uiso 1 1 calc R U . . .
H7B H 0.516926 0.785072 0.878634 0.042 Uiso 1 1 calc R U . . .
N8 N 0.6175(10) 0.7015(4) 0.82383(15) 0.0327(12) Uani 1 1 d . . . . .
O9 O 0.2980(9) 0.5624(3) 0.81015(13) 0.0406(11) Uani 1 1 d . . . . .
O10 O 0.9467(8) 0.8362(3) 0.83871(13) 0.0369(10) Uani 1 1 d . . . . .
C11 C 0.4756(12) 0.6254(5) 0.79578(18) 0.0324(14) Uani 1 1 d . . . . .
C12 C 0.5502(12) 0.6258(4) 0.74967(17) 0.0306(14) Uani 1 1 d . . . . .
C13 C 0.4110(12) 0.5552(4) 0.72041(18) 0.0328(14) Uani 1 1 d . . . . .
H13 H 0.269912 0.505940 0.730196 0.039 Uiso 1 1 calc R U . . .
C14 C 0.4765(12) 0.5557(4) 0.67603(18) 0.0326(15) Uani 1 1 d . . . . .
H14 H 0.384336 0.504127 0.656439 0.039 Uiso 1 1 calc R U . . .
C15 C 0.6703(12) 0.6289(4) 0.66034(18) 0.0328(15) Uani 1 1 d . . . . .
C16 C 0.8190(12) 0.7038(4) 0.69009(18) 0.0304(14) Uani 1 1 d . . . . .
C17 C 1.0348(12) 0.7778(4) 0.67727(19) 0.0333(14) Uani 1 1 d . . . . .
H17 H 1.082944 0.780057 0.647459 0.040 Uiso 1 1 calc R U . . .
C18 C 1.1742(13) 0.8457(4) 0.70714(19) 0.0348(15) Uani 1 1 d . . . . .
H18 H 1.317772 0.894644 0.697908 0.042 Uiso 1 1 calc R U . . .
C19 C 1.1072(12) 0.8439(4) 0.75109(18) 0.0321(14) Uani 1 1 d . . . . .
H19 H 1.204675 0.891883 0.771522 0.038 Uiso 1 1 calc R U . . .
C20 C 0.9018(12) 0.7732(4) 0.76506(18) 0.0325(14) Uani 1 1 d . . . . .
C21 C 0.8293(12) 0.7748(5) 0.81142(19) 0.0321(14) Uani 1 1 d . . . . .
C22 C 0.7565(12) 0.7009(4) 0.73478(17) 0.0292(14) Uani 1 1 d . . . . .
N23 N 0.7350(10) 0.6314(3) 0.61532(14) 0.0338(12) Uani 1 1 d . . . . .
C24 C 0.6645(14) 0.5305(5) 0.59026(19) 0.0403(16) Uani 1 1 d . . . . .
H24A H 0.456314 0.519903 0.588147 0.048 Uiso 1 1 calc R U . . .
H24B H 0.751069 0.464672 0.605296 0.048 Uiso 1 1 calc R U . . .
C25 C 0.7753(15) 0.5411(5) 0.54465(19) 0.0466(17) Uani 1 1 d . . . . .
H25A H 0.984570 0.547359 0.547014 0.056 Uiso 1 1 calc R U . . .
H25B H 0.725965 0.472876 0.527637 0.056 Uiso 1 1 calc R U . . .
O26 O 0.6596(9) 0.6364(3) 0.52181(13) 0.0485(12) Uani 1 1 d . . . . .
C27 C 0.7321(14) 0.7349(5) 0.54641(19) 0.0462(17) Uani 1 1 d . . . . .
H27A H 0.654175 0.801105 0.530597 0.055 Uiso 1 1 calc R U . . .
H27B H 0.941011 0.742656 0.549136 0.055 Uiso 1 1 calc R U . . .
C28 C 0.6166(13) 0.7303(5) 0.59154(19) 0.0385(15) Uani 1 1 d . . . . .
H28A H 0.669183 0.799078 0.607950 0.046 Uiso 1 1 calc R U . . .
H28B H 0.407128 0.725213 0.589046 0.046 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
N1 C2 1.334(9) . ?
N1 C6 1.339(8) . ?
C2 H2 0.9500 . ?
C2 C3 1.364(9) . ?
C3 H3 0.9500 . ?
C3 C4 1.391(9) . ?
C4 H4 0.9500 . ?
C4 C5 1.376(8) . ?
C5 C6 1.386(8) . ?
C5 C7 1.507(8) . ?
C6 H6 0.9500 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 N8 1.476(7) . ?
N8 C11 1.398(7) . ?
N8 C21 1.398(7) . ?
O9 C11 1.227(7) . ?
O10 C21 1.223(7) . ?
C11 C12 1.469(8) . ?
C12 C13 1.373(8) . ?
C12 C22 1.418(8) . ?
C13 H13 0.9500 . ?
C13 C14 1.406(8) . ?
C14 H14 0.9500 . ?
C14 C15 1.372(8) . ?
C15 C16 1.434(8) . ?
C15 N23 1.424(7) . ?
C16 C17 1.421(8) . ?
C16 C22 1.411(8) . ?
C17 H17 0.9500 . ?
C17 C18 1.366(8) . ?
C18 H18 0.9500 . ?
C18 C19 1.395(8) . ?
C19 H19 0.9500 . ?
C19 C20 1.372(8) . ?
C20 C21 1.474(8) . ?
C20 C22 1.418(8) . ?
N23 C24 1.460(7) . ?
N23 C28 1.484(7) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C24 C25 1.518(9) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C25 O26 1.431(7) . ?
O26 C27 1.431(7) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C27 C28 1.509(8) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?

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 N1 C6 116.0(6) . . ?
N1 C2 H2 118.0 . . ?
N1 C2 C3 123.9(6) . . ?
C3 C2 H2 118.0 . . ?
C2 C3 H3 120.6 . . ?
C2 C3 C4 118.9(6) . . ?
C4 C3 H3 120.6 . . ?
C3 C4 H4 120.5 . . ?
C5 C4 C3 119.1(6) . . ?
C5 C4 H4 120.5 . . ?
C4 C5 C6 117.1(5) . . ?
C4 C5 C7 121.7(5) . . ?
C6 C5 C7 121.1(5) . . ?
N1 C6 C5 124.9(6) . . ?
N1 C6 H6 117.5 . . ?
C5 C6 H6 117.5 . . ?
C5 C7 H7A 109.0 . . ?
C5 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
N8 C7 C5 112.8(5) . . ?
N8 C7 H7A 109.0 . . ?
N8 C7 H7B 109.0 . . ?
C11 N8 C7 118.7(5) . . ?
C21 N8 C7 116.5(5) . . ?
C21 N8 C11 124.8(5) . . ?
N8 C11 C12 117.0(5) . . ?
O9 C11 N8 119.8(5) . . ?
O9 C11 C12 123.2(5) . . ?
C13 C12 C11 119.4(5) . . ?
C13 C12 C22 119.7(5) . . ?
C22 C12 C11 120.8(5) . . ?
C12 C13 H13 119.9 . . ?
C12 C13 C14 120.2(5) . . ?
C14 C13 H13 119.9 . . ?
C13 C14 H14 119.2 . . ?
C15 C14 C13 121.5(5) . . ?
C15 C14 H14 119.2 . . ?
C14 C15 C16 119.5(5) . . ?
C14 C15 N23 122.1(5) . . ?
N23 C15 C16 118.4(5) . . ?
C17 C16 C15 123.4(5) . . ?
C22 C16 C15 118.5(5) . . ?
C22 C16 C17 118.0(5) . . ?
C16 C17 H17 119.5 . . ?
C18 C17 C16 121.0(5) . . ?
C18 C17 H17 119.5 . . ?
C17 C18 H18 119.7 . . ?
C17 C18 C19 120.5(6) . . ?
C19 C18 H18 119.7 . . ?
C18 C19 H19 119.7 . . ?
C20 C19 C18 120.5(5) . . ?
C20 C19 H19 119.7 . . ?
C19 C20 C21 119.6(5) . . ?
C19 C20 C22 120.0(5) . . ?
C22 C20 C21 120.4(5) . . ?
N8 C21 C20 117.2(5) . . ?
O10 C21 N8 119.9(5) . . ?
O10 C21 C20 122.9(5) . . ?
C12 C22 C20 119.7(5) . . ?
C16 C22 C12 120.5(5) . . ?
C16 C22 C20 119.8(5) . . ?
C15 N23 C24 115.7(4) . . ?
C15 N23 C28 113.3(4) . . ?
C24 N23 C28 109.5(4) . . ?
N23 C24 H24A 109.8 . . ?
N23 C24 H24B 109.8 . . ?
N23 C24 C25 109.3(5) . . ?
H24A C24 H24B 108.3 . . ?
C25 C24 H24A 109.8 . . ?
C25 C24 H24B 109.8 . . ?
C24 C25 H25A 109.2 . . ?
C24 C25 H25B 109.2 . . ?
H25A C25 H25B 107.9 . . ?
O26 C25 C24 111.9(5) . . ?
O26 C25 H25A 109.2 . . ?
O26 C25 H25B 109.2 . . ?
C27 O26 C25 109.1(4) . . ?
O26 C27 H27A 109.4 . . ?
O26 C27 H27B 109.4 . . ?
O26 C27 C28 111.2(5) . . ?
H27A C27 H27B 108.0 . . ?
C28 C27 H27A 109.4 . . ?
C28 C27 H27B 109.4 . . ?
N23 C28 C27 109.4(5) . . ?
N23 C28 H28A 109.8 . . ?
N23 C28 H28B 109.8 . . ?
C27 C28 H28A 109.8 . . ?
C27 C28 H28B 109.8 . . ?
H28A C28 H28B 108.3 . . ?

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
N1 C2 C3 C4 0.0(11) . . . . ?
C2 N1 C6 C5 -0.9(10) . . . . ?
C2 C3 C4 C5 -0.4(10) . . . . ?
C3 C4 C5 C6 0.2(9) . . . . ?
C3 C4 C5 C7 -179.9(5) . . . . ?
C4 C5 C6 N1 0.5(9) . . . . ?
C4 C5 C7 N8 117.1(6) . . . . ?
C5 C7 N8 C11 105.7(6) . . . . ?
C5 C7 N8 C21 -74.0(6) . . . . ?
C6 N1 C2 C3 0.6(10) . . . . ?
C6 C5 C7 N8 -62.9(7) . . . . ?
C7 C5 C6 N1 -179.5(6) . . . . ?
C7 N8 C11 O9 -1.7(7) . . . . ?
C7 N8 C11 C12 178.2(5) . . . . ?
C7 N8 C21 O10 1.8(7) . . . . ?
C7 N8 C21 C20 -178.6(5) . . . . ?
N8 C11 C12 C13 -177.9(5) . . . . ?
N8 C11 C12 C22 -0.3(7) . . . . ?
O9 C11 C12 C13 2.0(8) . . . . ?
O9 C11 C12 C22 179.7(5) . . . . ?
C11 N8 C21 O10 -177.9(5) . . . . ?
C11 N8 C21 C20 1.7(8) . . . . ?
C11 C12 C13 C14 179.0(5) . . . . ?
C11 C12 C22 C16 -177.5(5) . . . . ?
C11 C12 C22 C20 2.8(8) . . . . ?
C12 C13 C14 C15 -2.8(8) . . . . ?
C13 C12 C22 C16 0.1(8) . . . . ?
C13 C12 C22 C20 -179.5(5) . . . . ?
C13 C14 C15 C16 2.6(8) . . . . ?
C13 C14 C15 N23 -179.0(5) . . . . ?
C14 C15 C16 C17 176.2(5) . . . . ?
C14 C15 C16 C22 -1.1(8) . . . . ?
C14 C15 N23 C24 -20.5(8) . . . . ?
C14 C15 N23 C28 107.2(6) . . . . ?
C15 C16 C17 C18 -178.6(5) . . . . ?
C15 C16 C22 C12 -0.3(8) . . . . ?
C15 C16 C22 C20 179.4(5) . . . . ?
C15 N23 C24 C25 -173.7(5) . . . . ?
C15 N23 C28 C27 171.5(5) . . . . ?
C16 C15 N23 C24 157.9(5) . . . . ?
C16 C15 N23 C28 -74.4(6) . . . . ?
C16 C17 C18 C19 0.0(8) . . . . ?
C17 C16 C22 C12 -177.7(5) . . . . ?
C17 C16 C22 C20 1.9(8) . . . . ?
C17 C18 C19 C20 0.5(8) . . . . ?
C18 C19 C20 C21 -178.4(5) . . . . ?
C18 C19 C20 C22 0.3(8) . . . . ?
C19 C20 C21 N8 179.7(5) . . . . ?
C19 C20 C21 O10 -0.7(8) . . . . ?
C19 C20 C22 C12 178.2(5) . . . . ?
C19 C20 C22 C16 -1.5(8) . . . . ?
C21 N8 C11 O9 178.0(5) . . . . ?
C21 N8 C11 C12 -2.0(7) . . . . ?
C21 C20 C22 C12 -3.2(8) . . . . ?
C21 C20 C22 C16 177.1(5) . . . . ?
C22 C12 C13 C14 1.3(8) . . . . ?
C22 C16 C17 C18 -1.2(8) . . . . ?
C22 C20 C21 N8 1.0(8) . . . . ?
C22 C20 C21 O10 -179.4(5) . . . . ?
N23 C15 C16 C17 -2.2(8) . . . . ?
N23 C15 C16 C22 -179.6(5) . . . . ?
N23 C24 C25 O26 -58.5(7) . . . . ?
C24 N23 C28 C27 -57.7(6) . . . . ?
C24 C25 O26 C27 59.1(7) . . . . ?
C25 O26 C27 C28 -59.6(7) . . . . ?
O26 C27 C28 N23 59.4(7) . . . . ?
C28 N23 C24 C25 56.7(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
