# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_o1
_database_code_depnum_ccdc_archive 'CCDC 2339765'
loop_
_audit_author_name
_audit_author_address
'Peng Chen'
;Ningbo University
China
;
_audit_update_record             
;
2024-03-12 deposited with the CCDC.	2024-06-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H16 N2 O3'
_chemical_formula_weight         308.33

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

_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, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   18.137(14)
_cell_length_b                   9.160(7)
_cell_length_c                   9.370(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1557(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3826
_cell_measurement_theta_min      2.49
_cell_measurement_theta_max      24.84

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_F_000             648
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    0.091
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8403
_diffrn_reflns_av_unetI/netI     0.0207
_diffrn_reflns_av_R_equivalents  0.0197
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.223
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        24.997
_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 0.964
_diffrn_reflns_point_group_measured_fraction_full 0.964
_reflns_number_total             2642
_reflns_number_gt                2407
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.805
_reflns_Friedel_fraction_max     0.923
_reflns_Friedel_fraction_full    0.923

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0560P)²+0.0562P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 961 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(5)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2642
_refine_ls_number_parameters     208
_refine_ls_number_restraints     24
_refine_ls_R_factor_all          0.0506
_refine_ls_R_factor_gt           0.0455
_refine_ls_wR_factor_ref         0.1335
_refine_ls_wR_factor_gt          0.1293
_refine_ls_goodness_of_fit_ref   1.603
_refine_ls_restrained_S_all      1.823
_refine_ls_shift/su_max          0.008
_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 0.47404(15) 0.5825(3) 0.6293(3) 0.0596(7) Uani 1 1 d . . . . .
O2 O 0.52909(18) 0.2471(3) 0.6478(4) 0.0740(9) Uani 1 1 d . . . . .
O3 O 0.5557(3) 0.0129(5) 0.6709(7) 0.1416(18) Uani 1 1 d . U . . .
N1 N 0.39638(15) 0.5670(3) 0.4378(3) 0.0457(7) Uani 1 1 d . . . . .
N2 N 0.51078(15) 0.4592(3) 0.4316(3) 0.0501(8) Uani 1 1 d . . . . .
H2 H 0.498805 0.434308 0.346206 0.060 Uiso 1 1 calc R U . . .
C1 C 0.35581(17) 0.4760(4) 0.3454(3) 0.0419(7) Uani 1 1 d . . . . .
C2 C 0.36694(19) 0.3314(4) 0.3064(4) 0.0492(8) Uani 1 1 d . . . . .
H2A H 0.406714 0.278295 0.341446 0.059 Uiso 1 1 calc R U . . .
C3 C 0.3170(2) 0.2696(4) 0.2140(5) 0.0606(10) Uani 1 1 d . . . . .
H3 H 0.323578 0.173106 0.186037 0.073 Uiso 1 1 calc R U . . .
C4 C 0.2574(2) 0.3462(5) 0.1614(5) 0.0686(11) Uani 1 1 d . . . . .
H4 H 0.225375 0.300921 0.097668 0.082 Uiso 1 1 calc R U . . .
C5 C 0.2445(2) 0.4881(5) 0.2016(5) 0.0612(10) Uani 1 1 d . . . . .
H5 H 0.203833 0.538917 0.167257 0.073 Uiso 1 1 calc R U . . .
C6 C 0.29450(18) 0.5543(4) 0.2959(4) 0.0483(8) Uani 1 1 d . . . . .
C7 C 0.36027(18) 0.7021(4) 0.4482(4) 0.0468(8) Uani 1 1 d . . . . .
C8 C 0.3795(2) 0.8265(4) 0.5237(4) 0.0621(10) Uani 1 1 d . . . . .
H8 H 0.421104 0.828563 0.581780 0.074 Uiso 1 1 calc R U . . .
C9 C 0.3347(3) 0.9469(5) 0.5095(6) 0.0757(13) Uani 1 1 d . . . . .
H9 H 0.346446 1.031860 0.558752 0.091 Uiso 1 1 calc R U . . .
C10 C 0.2725(3) 0.9447(5) 0.4238(6) 0.0773(13) Uani 1 1 d . . . . .
H10 H 0.243451 1.028037 0.416585 0.093 Uiso 1 1 calc R U . . .
C11 C 0.2530(2) 0.8216(4) 0.3492(5) 0.0655(11) Uani 1 1 d . . . . .
H11 H 0.211015 0.820587 0.292365 0.079 Uiso 1 1 calc R U . . .
C12 C 0.29779(18) 0.6977(4) 0.3607(4) 0.0491(8) Uani 1 1 d . . . . .
C13 C 0.46340(18) 0.5369(4) 0.5085(4) 0.0439(8) Uani 1 1 d . . . . .
C14 C 0.58256(19) 0.4148(5) 0.4873(4) 0.0577(10) Uani 1 1 d . . . . .
H14A H 0.595546 0.477196 0.567107 0.069 Uiso 1 1 calc R U . . .
H14B H 0.619564 0.428060 0.413672 0.069 Uiso 1 1 calc R U . . .
C15 C 0.5832(2) 0.2596(5) 0.5352(5) 0.0728(12) Uani 1 1 d . . . . .
H15A H 0.570616 0.195438 0.456480 0.087 Uiso 1 1 calc R U . . .
H15B H 0.631664 0.233080 0.570260 0.087 Uiso 1 1 calc R U . . .
C16 C 0.5202(3) 0.1152(5) 0.7071(7) 0.0879(12) Uani 1 1 d . U . . .
C17 C 0.4616(4) 0.1203(9) 0.8172(9) 0.1165(17) Uani 1 1 d . U . . .
H17 H 0.459551 0.040904 0.878926 0.140 Uiso 1 1 calc R U . . .
C18 C 0.4148(4) 0.2169(8) 0.8373(8) 0.1098(16) Uani 1 1 d . U . . .
H18A H 0.413976 0.299069 0.779097 0.132 Uiso 1 1 calc R U . . .
H18B H 0.380679 0.207170 0.910740 0.132 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 C13 1.222(4) . ?
O2 C16 1.339(6) . ?
O2 C15 1.446(6) . ?
O3 C16 1.185(7) . ?
N1 C7 1.403(5) . ?
N1 C1 1.409(4) . ?
N1 C13 1.412(5) . ?
N2 C13 1.328(4) . ?
N2 C14 1.460(5) . ?
C1 C2 1.389(5) . ?
C1 C6 1.402(5) . ?
C2 C3 1.375(5) . ?
C3 C4 1.379(6) . ?
C4 C5 1.373(6) . ?
C5 C6 1.404(6) . ?
C6 C12 1.448(5) . ?
C7 C8 1.386(6) . ?
C7 C12 1.399(5) . ?
C8 C9 1.377(6) . ?
C9 C10 1.385(8) . ?
C10 C11 1.372(7) . ?
C11 C12 1.400(5) . ?
C14 C15 1.491(7) . ?
C16 C17 1.482(10) . ?
C17 C18 1.240(10) . ?

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
C16 O2 C15 117.1(4) . . ?
C7 N1 C1 108.7(3) . . ?
C7 N1 C13 122.8(3) . . ?
C1 N1 C13 128.5(3) . . ?
C13 N2 C14 122.2(3) . . ?
C2 C1 C6 121.0(3) . . ?
C2 C1 N1 130.6(3) . . ?
C6 C1 N1 108.4(3) . . ?
C3 C2 C1 117.5(3) . . ?
C2 C3 C4 122.2(4) . . ?
C5 C4 C3 121.1(4) . . ?
C4 C5 C6 118.2(4) . . ?
C1 C6 C5 120.0(4) . . ?
C1 C6 C12 107.0(3) . . ?
C5 C6 C12 133.0(3) . . ?
C8 C7 C12 121.8(3) . . ?
C8 C7 N1 130.0(3) . . ?
C12 C7 N1 108.2(3) . . ?
C9 C8 C7 117.4(4) . . ?
C8 C9 C10 121.7(4) . . ?
C11 C10 C9 121.1(4) . . ?
C10 C11 C12 118.6(4) . . ?
C7 C12 C11 119.4(4) . . ?
C7 C12 C6 107.8(3) . . ?
C11 C12 C6 132.8(4) . . ?
O1 C13 N2 125.7(3) . . ?
O1 C13 N1 120.2(3) . . ?
N2 C13 N1 114.1(3) . . ?
N2 C14 C15 112.3(4) . . ?
O2 C15 C14 106.9(3) . . ?
O3 C16 O2 121.9(6) . . ?
O3 C16 C17 127.8(6) . . ?
O2 C16 C17 110.3(5) . . ?
C18 C17 C16 128.3(8) . . ?

_refine_diff_density_max         0.386
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.037



