# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_1O
_database_code_depnum_ccdc_archive 'CCDC 2279131'
loop_
_audit_author_name
_audit_author_address
'Toshiyuki Sasaki'
;Japan Synchrotron Radiation Research Institute
Japan
;
_audit_update_record             
;
2023-07-04 deposited with the CCDC.	2024-04-11 downloaded from the CCDC.
;
_audit_creation_date             2023-07-04
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H10 N2 O3'
_chemical_formula_sum            'C13 H10 N2 O3'
_chemical_formula_weight         242.23
_chemical_absolute_configuration ?
_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 0.0000 0.0000 '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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0000 0.0000 '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           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   23.456
_cell_length_b                   3.811
_cell_length_c                   24.879
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2224.2
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2456
_cell_measurement_temperature    79
_cell_measurement_theta_max      0.9173833620062193
_cell_measurement_theta_min      0.16317160757312757
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.000
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             379
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.2254
_diffrn_reflns_av_unetI/netI     0.3167
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            21049
_diffrn_reflns_point_group_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        0.855
_diffrn_reflns_theta_max         0.855
_diffrn_reflns_theta_min         0.123
_diffrn_ambient_temperature      79
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  
;
Talos Arctica G2
;
_diffrn_measurement_method       ?
_diffrn_radiation_type           electrons
_diffrn_radiation_wavelength     0.02508
_diffrn_source                   ?
_reflns_Friedel_coverage         0.922
_reflns_Friedel_fraction_full    0.958
_reflns_Friedel_fraction_max     0.958
_reflns_number_gt                1186
_reflns_number_total             3836
_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       
'dials.two_theta_refine (Waterman et al., 2016)'
_computing_data_collection       
'Verlox (Thermo Fisher Scientific) and SerialEM (Mastronarde, 2005)'
_computing_data_reduction        'dials.scale (Beilsten-Edmands et al., 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.132
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 
;
 All f" are zero, so absolute structure could not be determined
;
_refine_ls_abs_structure_Flack   ?
_refine_ls_extinction_coef       233(38)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   0.902
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     328
_refine_ls_number_reflns         3836
_refine_ls_number_restraints     757
_refine_ls_R_factor_all          0.1925
_refine_ls_R_factor_gt           0.1215
_refine_ls_restrained_S_all      0.864
_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)+(0.1287P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2878
_refine_ls_wR_factor_ref         0.3097
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2. Restrained distances
 C26-C21 \\sim C26-C25 \\sim C24-C23 \\sim C23-C22 \\sim C22-C21 \\sim C15-C14
\\sim C16-C15 \\sim C17-C16
 \\sim C18-C17 \\sim C19-C18 \\sim C19-C14 \\sim C3-C2 \\sim C4-C3 \\sim
C25-C24 \\sim C5-C4 \\sim C6-C5 \\sim C6-
 C1 \\sim C2-C1 \\sim C8-C13 \\sim C9-C8 \\sim C9-C10 \\sim C11-C10 \\sim
C12-C11 \\sim C13-C12
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms restrained to be isotropic: with sigma of 0.005 and
sigma for terminal atoms of 0.005
Uanis(C12) \\sim Ueq: with sigma of 0.003 and sigma for terminal atoms of 0.005
4. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5.a Aromatic/amide H refined with riding coordinates:
 C25(H25), C19(H19), C4(H4A), C23(H23), C20(H20), C10(H10), C9(H9), C22(H22),
 C26(H26), C3(H3), C13(H13), C5(H5), C7(H7), C18(H18), C16(H16), C17(H17),
 C12(H12), C6(H6)
5.b Idealised tetrahedral OH refined as rotating group:
 O1(H1), O4(H4)
;
_atom_sites_solution_hydrogens   geom
_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
C25 C 0.7509(7) -0.189(4) 0.6301(8) 0.020(4) Uani 1 1 d D U . . .
H25 H 0.780827 -0.295797 0.611889 0.024 Uiso 1 1 calc R U . . .
C1 C 0.7322(6) 0.705(4) 0.4038(8) 0.016(4) Uani 1 1 d D U . . .
C19 C 0.4581(6) 0.276(4) 0.6212(10) 0.025(4) Uani 1 1 d D U . . .
H19 H 0.456573 0.181577 0.655642 0.030 Uiso 1 1 calc R U . . .
N1 N 0.6315(7) 0.810(4) 0.3963(11) 0.027(4) Uani 1 1 d . U . . .
N4 N 0.8068(7) -0.241(4) 0.7136(10) 0.017(3) Uani 1 1 d . U . . .
O6 O 0.8410(6) -0.403(4) 0.6919(9) 0.026(4) Uani 1 1 d . U . . .
O1 O 0.6785(6) 0.501(4) 0.4813(8) 0.028(4) Uani 1 1 d . U . . .
H1 H 0.651545 0.561199 0.462385 0.042 Uiso 1 1 calc R U . . .
C15 C 0.5137(6) 0.467(3) 0.5439(8) 0.014(3) Uani 1 1 d D U . . .
O5 O 0.8094(6) -0.168(4) 0.7630(10) 0.025(4) Uani 1 1 d . U . . .
C4 C 0.8283(7) 0.442(4) 0.4517(8) 0.023(4) Uani 1 1 d D U . . .
H4A H 0.861351 0.359751 0.468082 0.027 Uiso 1 1 calc R U . . .
N2 N 0.4398(8) 1.334(4) 0.2827(11) 0.028(4) Uani 1 1 d . U . . .
C21 C 0.6584(6) 0.075(4) 0.6317(7) 0.020(4) Uani 1 1 d D U . . .
C11 C 0.4901(6) 1.210(4) 0.3125(8) 0.014(3) Uani 1 1 d D U . . .
C23 C 0.7113(5) 0.033(4) 0.7122(8) 0.020(4) Uani 1 1 d D U . . .
H23 H 0.715578 0.077861 0.748682 0.023 Uiso 1 1 calc R U . . .
N3 N 0.6105(6) 0.206(3) 0.6000(9) 0.015(3) Uani 1 1 d . U . . .
O2 O 0.4461(7) 1.359(4) 0.2378(10) 0.032(4) Uani 1 1 d . U . . .
C20 C 0.5610(6) 0.192(4) 0.6202(11) 0.022(4) Uani 1 1 d . U . . .
H20 H 0.557842 0.102124 0.654767 0.026 Uiso 1 1 calc R U . . .
C10 C 0.5343(5) 1.042(3) 0.2838(8) 0.017(4) Uani 1 1 d D U . . .
H10 H 0.532614 1.020786 0.246569 0.020 Uiso 1 1 calc R U . . .
C9 C 0.5808(6) 0.908(4) 0.3126(8) 0.017(4) Uani 1 1 d D U . . .
H9 H 0.610002 0.796468 0.293976 0.021 Uiso 1 1 calc R U . . .
C22 C 0.6610(7) 0.127(5) 0.6871(8) 0.025(4) Uani 1 1 d D U . . .
H22 H 0.630468 0.220195 0.706179 0.030 Uiso 1 1 calc R U . . .
C26 C 0.7026(5) -0.092(4) 0.6027(9) 0.021(4) Uani 1 1 d D U . . .
H26 H 0.699076 -0.135278 0.566071 0.026 Uiso 1 1 calc R U . . .
C3 C 0.7770(5) 0.408(4) 0.4784(8) 0.021(4) Uani 1 1 d D U . . .
H3 H 0.775455 0.306101 0.512385 0.025 Uiso 1 1 calc R U . . .
C13 C 0.5378(5) 1.069(4) 0.3973(8) 0.027(4) Uani 1 1 d D U . . .
H13 H 0.536650 1.057559 0.434604 0.032 Uiso 1 1 calc R U . . .
C5 C 0.8321(6) 0.592(4) 0.4015(8) 0.019(4) Uani 1 1 d D U . . .
H5 H 0.867143 0.601139 0.384068 0.023 Uiso 1 1 calc R U . . .
C7 C 0.6783(7) 0.840(4) 0.3760(11) 0.024(4) Uani 1 1 d . U . . .
H7 H 0.681476 0.948389 0.342619 0.028 Uiso 1 1 calc R U . . .
C18 C 0.4082(7) 0.391(4) 0.5959(8) 0.029(4) Uani 1 1 d D U . . .
H18 H 0.372820 0.350267 0.611689 0.035 Uiso 1 1 calc R U . . .
C24 C 0.7554(7) -0.127(4) 0.6846(8) 0.018(4) Uani 1 1 d D U . . .
O3 O 0.4033(6) 1.469(3) 0.3100(8) 0.019(3) Uani 1 1 d . U . . .
C2 C 0.7270(6) 0.530(4) 0.4533(8) 0.021(4) Uani 1 1 d D U . . .
C16 C 0.4627(5) 0.584(4) 0.5192(8) 0.022(4) Uani 1 1 d D U . . .
H16 H 0.463519 0.671895 0.484381 0.027 Uiso 1 1 calc R U . . .
C17 C 0.4118(6) 0.568(3) 0.5470(7) 0.015(4) Uani 1 1 d D U . . .
H17 H 0.379596 0.675398 0.532796 0.018 Uiso 1 1 calc R U . . .
O4 O 0.5604(6) 0.489(4) 0.5145(9) 0.030(4) Uani 1 1 d . U . . .
H4 H 0.587691 0.417634 0.531903 0.046 Uiso 1 1 calc R U . . .
C12 C 0.4935(6) 1.217(4) 0.3685(8) 0.012(3) Uani 1 1 d D U . . .
H12 H 0.464395 1.327672 0.387482 0.014 Uiso 1 1 calc R U . . .
C6 C 0.7836(5) 0.733(3) 0.3766(9) 0.010(4) Uani 1 1 d D U . . .
H6 H 0.785767 0.840382 0.343137 0.012 Uiso 1 1 calc R U . . .
C14 C 0.5098(7) 0.303(4) 0.5946(9) 0.028(4) Uani 1 1 d D U . . .
C8 C 0.5847(6) 0.936(4) 0.3686(8) 0.019(4) Uani 1 1 d D 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
C25 H25 0.9300 . ?
C25 C26 1.373(16) . ?
C25 C24 1.378(17) . ?
C1 C7 1.53(3) . ?
C1 C2 1.406(17) . ?
C1 C6 1.385(15) . ?
C19 H19 0.9300 . ?
C19 C18 1.400(16) . ?
C19 C14 1.386(16) . ?
N1 C7 1.21(2) . ?
N1 C8 1.38(2) . ?
N4 O6 1.15(2) . ?
N4 O5 1.26(3) . ?
N4 C24 1.47(3) . ?
O1 H1 0.8200 . ?
O1 C2 1.34(2) . ?
C15 C16 1.415(15) . ?
C15 O4 1.32(2) . ?
C15 C14 1.412(18) . ?
C4 H4A 0.9300 . ?
C4 C3 1.382(15) . ?
C4 C5 1.376(17) . ?
N2 C11 1.47(3) . ?
N2 O2 1.13(3) . ?
N2 O3 1.21(2) . ?
C21 N3 1.46(2) . ?
C21 C22 1.394(17) . ?
C21 C26 1.414(16) . ?
C11 C10 1.414(15) . ?
C11 C12 1.395(17) . ?
C23 H23 0.9300 . ?
C23 C22 1.382(16) . ?
C23 C24 1.383(16) . ?
N3 C20 1.26(2) . ?
C20 H20 0.9300 . ?
C20 C14 1.42(2) . ?
C10 H10 0.9300 . ?
C10 C9 1.402(16) . ?
C9 H9 0.9300 . ?
C9 C8 1.400(17) . ?
C22 H22 0.9300 . ?
C26 H26 0.9300 . ?
C3 H3 0.9300 . ?
C3 C2 1.408(15) . ?
C13 H13 0.9300 . ?
C13 C12 1.384(16) . ?
C13 C8 1.405(16) . ?
C5 H5 0.9300 . ?
C5 C6 1.403(15) . ?
C7 H7 0.9300 . ?
C18 H18 0.9300 . ?
C18 C17 1.394(17) . ?
C16 H16 0.9300 . ?
C16 C17 1.380(15) . ?
C17 H17 0.9300 . ?
O4 H4 0.8200 . ?
C12 H12 0.9300 . ?
C6 H6 0.9300 . ?

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
C26 C25 H25 119.8 . . ?
C26 C25 C24 120.4(19) . . ?
C24 C25 H25 119.8 . . ?
C2 C1 C7 118.9(15) . . ?
C6 C1 C7 118.2(18) . . ?
C6 C1 C2 122.6(17) . . ?
C18 C19 H19 120.2 . . ?
C14 C19 H19 120.2 . . ?
C14 C19 C18 120(2) . . ?
C7 N1 C8 118(2) . . ?
O6 N4 O5 123(2) . . ?
O6 N4 C24 120(2) . . ?
O5 N4 C24 117.0(17) . . ?
C2 O1 H1 109.5 . . ?
O4 C15 C16 116.2(17) . . ?
O4 C15 C14 125.2(15) . . ?
C14 C15 C16 118.2(17) . . ?
C3 C4 H4A 118.9 . . ?
C5 C4 H4A 118.9 . . ?
C5 C4 C3 122.2(18) . . ?
O2 N2 C11 115(2) . . ?
O2 N2 O3 128(2) . . ?
O3 N2 C11 115(2) . . ?
C22 C21 N3 121.1(16) . . ?
C22 C21 C26 122.4(18) . . ?
C26 C21 N3 116.4(18) . . ?
C10 C11 N2 118.5(18) . . ?
C12 C11 N2 122.9(16) . . ?
C12 C11 C10 118.2(18) . . ?
C22 C23 H23 119.0 . . ?
C22 C23 C24 121.9(19) . . ?
C24 C23 H23 119.0 . . ?
C20 N3 C21 119(2) . . ?
N3 C20 H20 117.1 . . ?
N3 C20 C14 126(2) . . ?
C14 C20 H20 117.1 . . ?
C11 C10 H10 120.8 . . ?
C9 C10 C11 118.5(18) . . ?
C9 C10 H10 120.8 . . ?
C10 C9 H9 118.9 . . ?
C8 C9 C10 122.2(18) . . ?
C8 C9 H9 118.9 . . ?
C21 C22 H22 121.7 . . ?
C23 C22 C21 116.5(18) . . ?
C23 C22 H22 121.7 . . ?
C25 C26 C21 118.2(19) . . ?
C25 C26 H26 120.9 . . ?
C21 C26 H26 120.9 . . ?
C4 C3 H3 120.6 . . ?
C4 C3 C2 118.7(18) . . ?
C2 C3 H3 120.6 . . ?
C12 C13 H13 120.9 . . ?
C12 C13 C8 118.2(19) . . ?
C8 C13 H13 120.9 . . ?
C4 C5 H5 119.8 . . ?
C4 C5 C6 120.5(18) . . ?
C6 C5 H5 119.8 . . ?
C1 C7 H7 119.1 . . ?
N1 C7 C1 122(2) . . ?
N1 C7 H7 119.1 . . ?
C19 C18 H18 120.3 . . ?
C17 C18 C19 119.5(19) . . ?
C17 C18 H18 120.3 . . ?
C25 C24 N4 119.7(16) . . ?
C25 C24 C23 120.4(18) . . ?
C23 C24 N4 119.9(18) . . ?
C1 C2 C3 118.3(17) . . ?
O1 C2 C1 124.6(15) . . ?
O1 C2 C3 116.7(17) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 C15 120.0(18) . . ?
C17 C16 H16 120.0 . . ?
C18 C17 H17 119.6 . . ?
C16 C17 C18 120.8(17) . . ?
C16 C17 H17 119.6 . . ?
C15 O4 H4 109.5 . . ?
C11 C12 H12 118.3 . . ?
C13 C12 C11 123.4(19) . . ?
C13 C12 H12 118.3 . . ?
C1 C6 C5 117.5(19) . . ?
C1 C6 H6 121.3 . . ?
C5 C6 H6 121.3 . . ?
C19 C14 C15 121.1(19) . . ?
C19 C14 C20 120.2(19) . . ?
C15 C14 C20 118.5(16) . . ?
N1 C8 C9 121.4(17) . . ?
N1 C8 C13 119.6(19) . . ?
C9 C8 C13 118.8(18) . . ?

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
C19 C18 C17 C16 10(2) . . . . ?
O6 N4 C24 C25 -6(3) . . . . ?
O6 N4 C24 C23 172.5(16) . . . . ?
C15 C16 C17 C18 -9(2) . . . . ?
O5 N4 C24 C25 177.8(17) . . . . ?
O5 N4 C24 C23 -4(2) . . . . ?
C4 C3 C2 C1 -5(2) . . . . ?
C4 C3 C2 O1 -178.3(16) . . . . ?
C4 C5 C6 C1 -2(2) . . . . ?
N2 C11 C10 C9 -176.8(14) . . . . ?
N2 C11 C12 C13 173.1(14) . . . . ?
C21 N3 C20 C14 -178.8(16) . . . . ?
C11 C10 C9 C8 0(2) . . . . ?
N3 C21 C22 C23 -172.0(14) . . . . ?
N3 C21 C26 C25 173.7(14) . . . . ?
N3 C20 C14 C19 -179.6(17) . . . . ?
N3 C20 C14 C15 -5(3) . . . . ?
O2 N2 C11 C10 -18(3) . . . . ?
O2 N2 C11 C12 169.3(18) . . . . ?
C10 C11 C12 C13 0(2) . . . . ?
C10 C9 C8 N1 -178.4(14) . . . . ?
C10 C9 C8 C13 7(3) . . . . ?
C22 C21 N3 C20 -38(2) . . . . ?
C22 C21 C26 C25 -4(2) . . . . ?
C22 C23 C24 C25 2(3) . . . . ?
C22 C23 C24 N4 -176.6(15) . . . . ?
C26 C25 C24 N4 178.4(14) . . . . ?
C26 C25 C24 C23 0(3) . . . . ?
C26 C21 N3 C20 144.8(17) . . . . ?
C26 C21 C22 C23 5(3) . . . . ?
C3 C4 C5 C6 3(2) . . . . ?
C5 C4 C3 C2 0(2) . . . . ?
C7 C1 C2 O1 -7(3) . . . . ?
C7 C1 C2 C3 -179.9(16) . . . . ?
C7 C1 C6 C5 -177.0(15) . . . . ?
C7 N1 C8 C9 37(3) . . . . ?
C7 N1 C8 C13 -148.2(18) . . . . ?
C18 C19 C14 C15 5(3) . . . . ?
C18 C19 C14 C20 178.9(16) . . . . ?
C24 C25 C26 C21 1(2) . . . . ?
C24 C23 C22 C21 -4(2) . . . . ?
O3 N2 C11 C10 178.5(14) . . . . ?
O3 N2 C11 C12 6(3) . . . . ?
C2 C1 C7 N1 2(3) . . . . ?
C2 C1 C6 C5 -3(2) . . . . ?
C16 C15 C14 C19 -4(2) . . . . ?
C16 C15 C14 C20 -178.5(16) . . . . ?
O4 C15 C16 C17 179.4(15) . . . . ?
O4 C15 C14 C19 -176.4(17) . . . . ?
O4 C15 C14 C20 9(3) . . . . ?
C12 C11 C10 C9 -3(2) . . . . ?
C12 C13 C8 N1 175.2(15) . . . . ?
C12 C13 C8 C9 -10(2) . . . . ?
C6 C1 C7 N1 176.6(17) . . . . ?
C6 C1 C2 O1 179.1(17) . . . . ?
C6 C1 C2 C3 6(3) . . . . ?
C14 C19 C18 C17 -7(3) . . . . ?
C14 C15 C16 C17 6(2) . . . . ?
C8 N1 C7 C1 -179.5(16) . . . . ?
C8 C13 C12 C11 7(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: THF'
_chemical_properties_physical    'Mechanical stimuli-sensitive'
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_1Y
_database_code_depnum_ccdc_archive 'CCDC 2279132'
loop_
_audit_author_name
_audit_author_address
'Toshiyuki Sasaki'
;Japan Synchrotron Radiation Research Institute
Japan
;
_audit_update_record             
;
2023-07-04 deposited with the CCDC.	2024-04-11 downloaded from the CCDC.
;
_audit_creation_date             2023-04-19
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H10 N2 O3'
_chemical_formula_sum            'C13 H10 N2 O3'
_chemical_formula_weight         242.23
_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 0.0000 0.0000 '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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0000 0.0000 '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                   12.450
_cell_length_b                   5.735
_cell_length_c                   15.344
_cell_angle_alpha                90
_cell_angle_beta                 97.73
_cell_angle_gamma                90
_cell_volume                     1085.6
_cell_formula_units_Z            4
_cell_measurement_reflns_used    42756
_cell_measurement_temperature    79
_cell_measurement_theta_max      1.1916586979282382
_cell_measurement_theta_min      0.13525662239357933
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.000
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.482
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       columnar
_exptl_crystal_F_000             189
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.2378
_diffrn_reflns_av_unetI/netI     0.0847
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            208643
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        0.862
_diffrn_reflns_theta_max         0.957
_diffrn_reflns_theta_min         0.134
_diffrn_ambient_temperature      79
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  
;
Talos Arctica G2
;
_diffrn_measurement_method       ?
_diffrn_radiation_type           electrons
_diffrn_radiation_wavelength     0.02508
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2180
_reflns_number_total             2657
_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       
'dials.two_theta_refine (Waterman et al., 2016)'
_computing_data_collection       
'Verlox (Thermo Fisher Scientific) and SerialEM (Mastronarde, 2005)'
_computing_data_reduction        'dials.scale (Beilsten-Edmands et al., 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       7285(27)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.253
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2657
_refine_ls_number_restraints     306
_refine_ls_R_factor_all          0.1972
_refine_ls_R_factor_gt           0.1774
_refine_ls_restrained_S_all      1.197
_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)+(0.1613P)²+0.9315P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4428
_refine_ls_wR_factor_ref         0.4522
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2. Restrained distances
 C6-C1 \\sim C2-C1 \\sim C3-C2 \\sim C4-C3 \\sim C5-C4 \\sim C6-C5 \\sim C8-C13
\\sim C9-C8 \\sim C9-C10 \\sim C11-
 C10 \\sim C12-C11 \\sim C13-C12
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms restrained to be isotropic: with sigma of 0.005 and
sigma for terminal atoms of 0.01
4. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C7(H7), C13(H13), C3(H3), C5(H5), C6(H6), C10(H10), C12(H12), C9(H9)
5.b Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_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
N2 N -0.0220(5) 0.6341(11) 0.3634(5) 0.0154(13) Uani 1 1 d . U . . .
O1 O 0.5493(4) 0.1159(10) 0.5834(4) 0.0139(12) Uani 1 1 d . U . . .
H1 H 0.491563 0.166658 0.558710 0.021 Uiso 1 1 calc R U . . .
O3 O -0.0667(5) 0.8122(12) 0.3836(5) 0.0255(15) Uani 1 1 d . U . . .
C4 C 0.7463(5) 0.3798(11) 0.7509(5) 0.0119(14) Uani 1 1 d D U . . .
H4 H 0.813352 0.344137 0.782427 0.014 Uiso 1 1 calc R U . . .
N1 N 0.3849(5) 0.4145(11) 0.5560(4) 0.0110(12) Uani 1 1 d . U . . .
C7 C 0.4422(5) 0.5584(11) 0.6074(5) 0.0103(14) Uani 1 1 d . U . . .
H7 H 0.415488 0.707424 0.615126 0.012 Uiso 1 1 calc R U . . .
C2 C 0.5953(5) 0.2747(11) 0.6409(5) 0.0123(14) Uani 1 1 d D U . . .
O2 O -0.0537(5) 0.5102(11) 0.3022(5) 0.0219(14) Uani 1 1 d . U . . .
C1 C 0.5468(5) 0.4936(11) 0.6534(5) 0.0128(14) Uani 1 1 d D U . . .
C13 C 0.2272(5) 0.6852(12) 0.5267(5) 0.0134(15) Uani 1 1 d D U . . .
H13 H 0.258783 0.790206 0.568711 0.016 Uiso 1 1 calc R U . . .
C3 C 0.6946(5) 0.2157(11) 0.6910(4) 0.0117(14) Uani 1 1 d D U . . .
H3 H 0.725720 0.070256 0.684682 0.014 Uiso 1 1 calc R U . . .
C5 C 0.6982(5) 0.5963(11) 0.7637(5) 0.0140(15) Uani 1 1 d D U . . .
H5 H 0.731598 0.702112 0.804553 0.017 Uiso 1 1 calc R U . . .
C8 C 0.2816(5) 0.4790(11) 0.5125(4) 0.0100(13) Uani 1 1 d D U . . .
C6 C 0.6000(5) 0.6486(12) 0.7140(5) 0.0132(14) Uani 1 1 d D U . . .
H6 H 0.568379 0.792911 0.721598 0.016 Uiso 1 1 calc R U . . .
C10 C 0.1323(5) 0.3618(11) 0.4026(5) 0.0146(15) Uani 1 1 d D U . . .
H10 H 0.100368 0.254897 0.361444 0.018 Uiso 1 1 calc R U . . .
C12 C 0.1266(5) 0.7375(11) 0.4792(4) 0.0117(14) Uani 1 1 d D U . . .
H12 H 0.090237 0.874824 0.488805 0.014 Uiso 1 1 calc R U . . .
C11 C 0.0827(5) 0.5745(11) 0.4165(5) 0.0134(14) Uani 1 1 d D U . . .
C9 C 0.2317(5) 0.3169(12) 0.4528(5) 0.0131(14) Uani 1 1 d D U . . .
H9 H 0.265631 0.174685 0.446371 0.016 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
N2 O3 1.223(9) . ?
N2 O2 1.201(9) . ?
N2 C11 1.481(9) . ?
O1 H1 0.8200 . ?
O1 C2 1.342(9) . ?
C4 H4 0.9300 . ?
C4 C3 1.409(8) . ?
C4 C5 1.403(8) . ?
N1 C7 1.289(9) . ?
N1 C8 1.416(9) . ?
C7 H7 0.9300 . ?
C7 C1 1.444(10) . ?
C2 C1 1.417(8) . ?
C2 C3 1.406(8) . ?
C1 C6 1.389(8) . ?
C13 H13 0.9300 . ?
C13 C8 1.394(8) . ?
C13 C12 1.395(8) . ?
C3 H3 0.9300 . ?
C5 H5 0.9300 . ?
C5 C6 1.384(8) . ?
C8 C9 1.391(8) . ?
C6 H6 0.9300 . ?
C10 H10 0.9300 . ?
C10 C11 1.397(8) . ?
C10 C9 1.391(8) . ?
C12 H12 0.9300 . ?
C12 C11 1.399(8) . ?
C9 H9 0.9300 . ?

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
O3 N2 C11 116.7(6) . . ?
O2 N2 O3 125.4(7) . . ?
O2 N2 C11 117.8(6) . . ?
C2 O1 H1 109.5 . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C5 C4 C3 121.1(6) . . ?
C7 N1 C8 120.9(6) . . ?
N1 C7 H7 119.2 . . ?
N1 C7 C1 121.5(6) . . ?
C1 C7 H7 119.2 . . ?
O1 C2 C1 122.5(6) . . ?
O1 C2 C3 117.5(6) . . ?
C3 C2 C1 119.9(6) . . ?
C2 C1 C7 122.3(6) . . ?
C6 C1 C7 118.7(6) . . ?
C6 C1 C2 119.0(6) . . ?
C8 C13 H13 119.3 . . ?
C8 C13 C12 121.4(6) . . ?
C12 C13 H13 119.3 . . ?
C4 C3 H3 120.5 . . ?
C2 C3 C4 119.1(6) . . ?
C2 C3 H3 120.5 . . ?
C4 C5 H5 120.8 . . ?
C6 C5 C4 118.5(6) . . ?
C6 C5 H5 120.8 . . ?
C13 C8 N1 125.3(6) . . ?
C9 C8 N1 115.6(6) . . ?
C9 C8 C13 119.1(6) . . ?
C1 C6 H6 118.8 . . ?
C5 C6 C1 122.4(6) . . ?
C5 C6 H6 118.8 . . ?
C11 C10 H10 121.4 . . ?
C9 C10 H10 121.4 . . ?
C9 C10 C11 117.1(6) . . ?
C13 C12 H12 121.4 . . ?
C13 C12 C11 117.1(6) . . ?
C11 C12 H12 121.4 . . ?
C10 C11 N2 119.5(6) . . ?
C10 C11 C12 123.3(6) . . ?
C12 C11 N2 117.2(6) . . ?
C8 C9 H9 119.1 . . ?
C10 C9 C8 121.8(6) . . ?
C10 C9 H9 119.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 C1 C7 2.3(11) . . . . ?
O1 C2 C1 C6 -179.8(6) . . . . ?
O1 C2 C3 C4 178.9(6) . . . . ?
O3 N2 C11 C10 173.6(7) . . . . ?
O3 N2 C11 C12 -6.1(9) . . . . ?
C4 C5 C6 C1 1.1(10) . . . . ?
N1 C7 C1 C2 3.7(10) . . . . ?
N1 C7 C1 C6 -174.1(6) . . . . ?
N1 C8 C9 C10 -177.0(6) . . . . ?
C7 N1 C8 C13 -7.0(10) . . . . ?
C7 N1 C8 C9 174.5(6) . . . . ?
C7 C1 C6 C5 177.2(6) . . . . ?
C2 C1 C6 C5 -0.8(10) . . . . ?
O2 N2 C11 C10 -9.5(10) . . . . ?
O2 N2 C11 C12 170.8(7) . . . . ?
C1 C2 C3 C4 -2.3(10) . . . . ?
C13 C8 C9 C10 4.4(10) . . . . ?
C13 C12 C11 N2 -177.5(6) . . . . ?
C13 C12 C11 C10 2.8(10) . . . . ?
C3 C4 C5 C6 -2.0(10) . . . . ?
C3 C2 C1 C7 -176.5(6) . . . . ?
C3 C2 C1 C6 1.4(10) . . . . ?
C5 C4 C3 C2 2.6(10) . . . . ?
C8 N1 C7 C1 178.9(6) . . . . ?
C8 C13 C12 C11 -0.2(10) . . . . ?
C12 C13 C8 N1 178.3(6) . . . . ?
C12 C13 C8 C9 -3.3(10) . . . . ?
C11 C10 C9 C8 -2.0(10) . . . . ?
C9 C10 C11 N2 178.6(6) . . . . ?
C9 C10 C11 C12 -1.7(10) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: THF'
_exptl_crystal_preparation       Luminescent
