# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 2296018'
loop_
_audit_author_name
_audit_author_address
'Dejan-Kresimir Bucar'
;University College London
United Kingdom
;
_audit_update_record             
;
2023-09-19 deposited with the CCDC.	2023-10-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_formula_moiety         'C12 H12 N2 O2'
_chemical_formula_sum            'C12 H12 N2 O2'
_chemical_formula_weight         216.24

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.96490(10)
_cell_length_b                   8.25850(10)
_cell_length_c                   20.8574(2)
_cell_angle_alpha                90
_cell_angle_beta                 106.9280(10)
_cell_angle_gamma                90
_cell_volume                     2136.45(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    150.0(1)
_cell_measurement_reflns_used    27976
_cell_measurement_theta_min      3.5590
_cell_measurement_theta_max      78.3880

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-7 0 -2 0.0548
-5 4 -1 0.0771
2 0 -14 0.0628
3 -4 -8 0.0793
-1 -3 10 0.0669
-3 4 8 0.0747
1 3 -11 0.0775
-2 0 14 0.0552
6 2 -10 0.0685
0 5 -2 0.0887
-7 0 11 0.0485
-4 -4 8 0.0666
6 1 -11 0.0704
-8 -1 2 0.0582
-8 0 2 0.0533
3 -5 0 0.0931
7 0 2 0.0473
4 4 2 0.0873
-6 -3 -2 0.0676
6 -1 6 0.0551
-6 0 -7 0.0591
-2 -5 -4 0.0764
-5 0 -9 0.0574
-4 -2 -8 0.0673
-2 -2 -10 0.0653
-2 0 -11 0.0564
0 5 5 0.0791
-3 3 -9 0.0683
0 -5 -6 0.0743
3 -1 11 0.0617
1 -2 -12 0.0634
1 -4 -8 0.0739
0 0 -13 0.0570
0 2 -12 0.0605
_exptl_absorpt_coefficient_mu    0.763
_exptl_absorpt_correction_T_min  0.908
_exptl_absorpt_correction_T_max  0.937
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      150.0(1)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'SuperNova, Dual, Cu at home/near, HyPix-Arc 100'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            'HyPix-Arc 100'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            49635
_diffrn_reflns_av_unetI/netI     0.0126
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.564
_diffrn_reflns_theta_max         66.601
_diffrn_reflns_theta_full        66.601
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3775
_reflns_number_gt                3373
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.42.60a (Rigaku OD, 2022)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.60a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.60a (Rigaku OD, 2022)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0522P)²+0.4339P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'dual-space method (Sheldrick et al., 2001)'
_atom_sites_solution_secondary   notdet
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3775
_refine_ls_number_parameters     291
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0372
_refine_ls_R_factor_gt           0.0334
_refine_ls_wR_factor_ref         0.0936
_refine_ls_wR_factor_gt          0.0909
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.65202(6) 0.92321(11) 0.42710(4) 0.0392(2) Uani 1 1 d . . . . .
O2 O 0.96804(6) 0.54309(10) 0.39866(4) 0.0341(2) Uani 1 1 d . . . . .
O3 O 0.67163(7) 0.38141(12) 0.33124(4) 0.0409(2) Uani 1 1 d . . . . .
O4 O 0.90620(6) 0.08387(10) 0.55204(4) 0.0374(2) Uani 1 1 d . . . . .
N1 N 0.83076(7) 0.71598(11) 0.35463(4) 0.0267(2) Uani 1 1 d . . . . .
N2 N 0.74874(7) 0.82035(11) 0.36217(4) 0.0279(2) Uani 1 1 d . . . . .
N3 N 0.76836(7) 0.24872(11) 0.49992(4) 0.0279(2) Uani 1 1 d . . . . .
N4 N 0.70383(7) 0.32367(11) 0.44104(4) 0.0281(2) Uani 1 1 d . . . . .
C1 C 0.72761(9) 0.83842(14) 0.42220(5) 0.0302(3) Uani 1 1 d . . . . .
C2 C 0.79847(9) 0.75036(15) 0.47860(5) 0.0328(3) Uani 1 1 d . . . . .
H2 H 0.789794 0.764614 0.521442 0.039 Uiso 1 1 calc R U . . .
C3 C 0.87493(9) 0.65062(14) 0.47152(5) 0.0303(3) Uani 1 1 d . . . . .
H3 H 0.916267 0.592067 0.508821 0.036 Uiso 1 1 calc R U . . .
C4 C 0.89589(8) 0.63034(13) 0.40690(5) 0.0275(2) Uani 1 1 d . . . . .
C5 C 0.85848(8) 0.72332(13) 0.29224(5) 0.0259(2) Uani 1 1 d . . . . .
C6 C 0.81019(9) 0.61742(14) 0.24123(5) 0.0312(3) Uani 1 1 d . . . . .
H6 H 0.759038 0.541870 0.246503 0.037 Uiso 1 1 calc R U . . .
C7 C 0.83838(9) 0.62417(16) 0.18186(6) 0.0353(3) Uani 1 1 d . . . . .
H7 H 0.806244 0.552711 0.146621 0.042 Uiso 1 1 calc R U . . .
C8 C 0.91342(9) 0.73560(15) 0.17461(5) 0.0349(3) Uani 1 1 d . . . . .
H8 H 0.931595 0.740711 0.134197 0.042 Uiso 1 1 calc R U . . .
C9 C 0.96207(9) 0.83981(16) 0.22647(6) 0.0364(3) Uani 1 1 d . . . . .
H9 H 1.013349 0.915193 0.221246 0.044 Uiso 1 1 calc R U . . .
C10 C 0.93541(9) 0.83344(15) 0.28625(6) 0.0319(3) Uani 1 1 d . . . . .
H10 H 0.969045 0.902730 0.321973 0.038 Uiso 1 1 calc R U . . .
C11 C 0.66990(9) 0.88318(16) 0.30180(6) 0.0367(3) Uani 1 1 d . . . . .
H11A H 0.705839 0.902566 0.267167 0.044 Uiso 1 1 calc R U . . .
H11B H 0.641978 0.987028 0.312274 0.044 Uiso 1 1 calc R U . . .
C12 C 0.57707(10) 0.7679(2) 0.27494(6) 0.0490(4) Uani 1 1 d . . . . .
H12A H 0.521518 0.820735 0.239720 0.073 Uiso 1 1 calc R U . . .
H12B H 0.547644 0.736363 0.310858 0.073 Uiso 1 1 calc R U . . .
H12C H 0.602380 0.672426 0.256990 0.073 Uiso 1 1 calc R U . . .
C13 C 0.72850(9) 0.31330(15) 0.38192(5) 0.0310(3) Uani 1 1 d . . . . .
C14 C 0.82534(9) 0.22221(15) 0.38331(6) 0.0331(3) Uani 1 1 d . . . . .
H14 H 0.845863 0.214007 0.343764 0.040 Uiso 1 1 calc R U . . .
C15 C 0.88572(9) 0.15026(14) 0.43853(5) 0.0310(3) Uani 1 1 d . . . . .
H15 H 0.948269 0.094294 0.437333 0.037 Uiso 1 1 calc R U . . .
C16 C 0.85652(9) 0.15674(14) 0.50091(5) 0.0294(3) Uani 1 1 d . . . . .
C17 C 0.73153(8) 0.25120(13) 0.55885(5) 0.0270(2) Uani 1 1 d . . . . .
C18 C 0.64590(9) 0.15465(15) 0.56173(6) 0.0313(3) Uani 1 1 d . . . . .
H18 H 0.609986 0.089442 0.525089 0.038 Uiso 1 1 calc R U . . .
C19 C 0.61382(9) 0.15573(15) 0.61986(6) 0.0355(3) Uani 1 1 d . . . . .
H19 H 0.554340 0.093512 0.622263 0.043 Uiso 1 1 calc R U . . .
C20 C 0.66957(9) 0.24848(16) 0.67409(6) 0.0369(3) Uani 1 1 d . . . . .
H20 H 0.648077 0.248567 0.713421 0.044 Uiso 1 1 calc R U . . .
C21 C 0.75672(9) 0.34106(16) 0.67081(6) 0.0373(3) Uani 1 1 d . . . . .
H21 H 0.794869 0.402318 0.708182 0.045 Uiso 1 1 calc R U . . .
C22 C 0.78821(9) 0.34410(15) 0.61274(6) 0.0327(3) Uani 1 1 d . . . . .
H22 H 0.846841 0.407960 0.610079 0.039 Uiso 1 1 calc R U . . .
C23 C 0.61534(9) 0.43122(15) 0.44461(6) 0.0360(3) Uani 1 1 d . . . . .
H23A H 0.615786 0.527230 0.417077 0.043 Uiso 1 1 calc R U . . .
H23B H 0.628419 0.467440 0.491037 0.043 Uiso 1 1 calc R U . . .
C24 C 0.50489(10) 0.3535(2) 0.42134(7) 0.0506(4) Uani 1 1 d . . . . .
H24A H 0.449882 0.436661 0.414212 0.076 Uiso 1 1 calc R U . . .
H24B H 0.496607 0.278159 0.455178 0.076 Uiso 1 1 calc R U . . .
H24C H 0.497446 0.295838 0.379710 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
O1 C1 1.2326(14) . ?
O2 C4 1.2319(13) . ?
O3 C13 1.2343(14) . ?
O4 C16 1.2306(14) . ?
N1 C4 1.3659(14) . ?
N1 N2 1.4127(12) . ?
N1 C5 1.4487(13) . ?
N2 C1 1.3656(14) . ?
N2 C11 1.4664(14) . ?
N3 C16 1.3676(14) . ?
N3 N4 1.4118(12) . ?
N3 C17 1.4424(13) . ?
N4 C13 1.3639(13) . ?
N4 C23 1.4697(14) . ?
C1 C2 1.4586(16) . ?
C2 C3 1.3297(16) . ?
C3 C4 1.4600(15) . ?
C5 C6 1.3787(15) . ?
C5 C10 1.3821(15) . ?
C6 C7 1.3906(16) . ?
C7 C8 1.3791(17) . ?
C8 C9 1.3824(17) . ?
C9 C10 1.3885(15) . ?
C11 C12 1.5087(19) . ?
C13 C14 1.4567(16) . ?
C14 C15 1.3294(16) . ?
C15 C16 1.4581(14) . ?
C17 C18 1.3824(16) . ?
C17 C22 1.3825(16) . ?
C18 C19 1.3918(15) . ?
C19 C20 1.3829(17) . ?
C20 C21 1.3824(17) . ?
C21 C22 1.3864(15) . ?
C23 C24 1.5144(18) . ?

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
C4 N1 N2 122.51(8) . . ?
C4 N1 C5 118.77(8) . . ?
N2 N1 C5 117.78(8) . . ?
C1 N2 N1 121.82(9) . . ?
C1 N2 C11 118.22(9) . . ?
N1 N2 C11 118.64(8) . . ?
C16 N3 N4 122.53(8) . . ?
C16 N3 C17 118.53(9) . . ?
N4 N3 C17 118.40(8) . . ?
C13 N4 N3 121.56(9) . . ?
C13 N4 C23 118.40(9) . . ?
N3 N4 C23 119.64(8) . . ?
O1 C1 N2 120.98(10) . . ?
O1 C1 C2 123.07(10) . . ?
N2 C1 C2 115.94(10) . . ?
C3 C2 C1 122.29(10) . . ?
C2 C3 C4 121.25(10) . . ?
O2 C4 N1 120.63(9) . . ?
O2 C4 C3 123.29(10) . . ?
N1 C4 C3 116.07(9) . . ?
C6 C5 C10 121.68(10) . . ?
C6 C5 N1 119.40(9) . . ?
C10 C5 N1 118.88(9) . . ?
C5 C6 C7 118.93(10) . . ?
C8 C7 C6 120.07(11) . . ?
C7 C8 C9 120.36(10) . . ?
C8 C9 C10 120.19(11) . . ?
C5 C10 C9 118.75(10) . . ?
N2 C11 C12 112.13(10) . . ?
O3 C13 N4 120.45(10) . . ?
O3 C13 C14 123.30(10) . . ?
N4 C13 C14 116.23(10) . . ?
C15 C14 C13 122.34(10) . . ?
C14 C15 C16 121.08(10) . . ?
O4 C16 N3 120.59(9) . . ?
O4 C16 C15 123.30(10) . . ?
N3 C16 C15 116.10(10) . . ?
C18 C17 C22 121.88(10) . . ?
C18 C17 N3 119.88(10) . . ?
C22 C17 N3 118.12(10) . . ?
C17 C18 C19 118.80(10) . . ?
C20 C19 C18 119.90(11) . . ?
C21 C20 C19 120.40(10) . . ?
C20 C21 C22 120.41(11) . . ?
C17 C22 C21 118.57(11) . . ?
N4 C23 C24 114.00(11) . . ?

_refine_diff_density_max         0.123
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.039

