# 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_Zhu75
_database_code_depnum_ccdc_archive 'CCDC 2348559'
loop_
_audit_author_name
_audit_author_address
'Dao-Wen Luo'
;Instrument Centre of National Chung Hsing University
Taiwan
;
_audit_update_record             
;
2024-04-16 deposited with the CCDC.	2024-06-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C18 H20 N2 O4'
_chemical_formula_sum            'C18 H20 N2 O4'
_chemical_melting_point          ?

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            colourless
_diffrn_ambient_temperature      150(2)
_chemical_formula_weight         328.36

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      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-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                   30.9203(18)
_cell_length_b                   6.8974(3)
_cell_length_c                   22.2984(13)
_cell_angle_alpha                90
_cell_angle_beta                 133.015(4)
_cell_angle_gamma                90
_cell_volume                     3477.2(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9964
_cell_measurement_theta_min      3.555
_cell_measurement_theta_max      27.885
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_F_000             1392
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.330
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.089
_shelx_estimated_absorpt_T_min   0.969
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6918
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            61833
_diffrn_reflns_av_unetI/netI     0.0185
_diffrn_reflns_av_R_equivalents  0.0417
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         3.088
_diffrn_reflns_theta_max         27.921
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4150
_reflns_number_gt                3603
_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       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V7.34A (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT V7.34A (Bruker AXS, 2006)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL
_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)+(0.0788P)²+2.5711P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4150
_refine_ls_number_parameters     233
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0477
_refine_ls_R_factor_gt           0.0392
_refine_ls_wR_factor_ref         0.1291
_refine_ls_wR_factor_gt          0.1149
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.013
_refine_ls_shift/su_max          0.000
_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 0.45757(4) 0.68666(15) 0.56895(7) 0.0409(3) Uani 1 1 d . . . . .
O2 O 0.48493(4) 0.40897(14) 0.64121(5) 0.0290(2) Uani 1 1 d . . . . .
O3 O 0.19873(4) 0.27777(13) 0.21377(5) 0.0266(2) Uani 1 1 d . . . . .
O4 O 0.14975(4) 0.56246(12) 0.17174(5) 0.0231(2) Uani 1 1 d . . . . .
N1 N 0.36837(5) 0.10976(16) 0.55253(7) 0.0294(2) Uani 1 1 d . . . . .
N2 N 0.21570(5) 0.87268(15) 0.33317(7) 0.0293(2) Uani 1 1 d . . . . .
C1 C 0.33824(5) 0.54866(16) 0.44567(7) 0.0190(2) Uani 1 1 d . . . . .
H1A H 0.3554(7) 0.632(2) 0.4317(9) 0.025(4) Uiso 1 1 d . . . . .
C2 C 0.28912(5) 0.42183(16) 0.37844(6) 0.0181(2) Uani 1 1 d . . . . .
H2A H 0.2980(7) 0.329(2) 0.3554(9) 0.026(4) Uiso 1 1 d . . . . .
C3 C 0.24239(5) 0.36652(16) 0.37781(7) 0.0188(2) Uani 1 1 d . . . . .
H3A H 0.2238(7) 0.242(2) 0.3525(9) 0.025(4) Uiso 1 1 d . . . . .
C4 C 0.24595(5) 0.44120(17) 0.44342(7) 0.0218(2) Uani 1 1 d . . . . .
H4A H 0.215693 0.407076 0.442417 0.026 Uiso 1 1 calc R U . . .
C5 C 0.28992(5) 0.55416(17) 0.50359(7) 0.0227(2) Uani 1 1 d . . . . .
H5A H 0.290332 0.595968 0.544569 0.027 Uiso 1 1 calc R U . . .
C6 C 0.33827(5) 0.61714(16) 0.50901(7) 0.0212(2) Uani 1 1 d . . . . .
H6A H 0.3569(7) 0.740(2) 0.5345(10) 0.029(4) Uiso 1 1 d . . . . .
C7 C 0.38444(5) 0.46324(16) 0.53218(7) 0.0194(2) Uani 1 1 d . . . . .
C8 C 0.37635(5) 0.26623(17) 0.54480(7) 0.0203(2) Uani 1 1 d . . . . .
C9 C 0.44676(5) 0.53442(18) 0.58266(7) 0.0240(2) Uani 1 1 d . . . . .
C10 C 0.55008(5) 0.4445(3) 0.69950(8) 0.0373(3) Uani 1 1 d . . . . .
C11 C 0.56885(6) 0.4565(3) 0.65259(9) 0.0407(4) Uani 1 1 d . . . . .
H11A H 0.611556 0.479769 0.690852 0.061 Uiso 1 1 calc R U . . .
H11B H 0.559388 0.334340 0.623349 0.061 Uiso 1 1 calc R U . . .
H11C H 0.547812 0.563227 0.613021 0.061 Uiso 1 1 calc R U . . .
C12 C 0.56555(8) 0.6215(4) 0.74970(12) 0.0796(9) Uani 1 1 d . . . . .
H12A H 0.608277 0.644303 0.787823 0.119 Uiso 1 1 calc R U . . .
H12B H 0.544461 0.733783 0.713375 0.119 Uiso 1 1 calc R U . . .
H12C H 0.554041 0.602307 0.780768 0.119 Uiso 1 1 calc R U . . .
C13 C 0.57396(8) 0.2622(5) 0.75076(17) 0.1038(12) Uani 1 1 d . . . . .
H13A H 0.617276 0.267333 0.792347 0.156 Uiso 1 1 calc R U . . .
H13B H 0.559049 0.252006 0.777801 0.156 Uiso 1 1 calc R U . . .
H13C H 0.561058 0.149106 0.715408 0.156 Uiso 1 1 calc R U . . .
C14 C 0.22805(5) 0.51411(15) 0.31321(6) 0.0176(2) Uani 1 1 d . . . . .
C15 C 0.22059(5) 0.71498(16) 0.32276(7) 0.0203(2) Uani 1 1 d . . . . .
C16 C 0.19148(5) 0.43682(16) 0.22820(7) 0.0194(2) Uani 1 1 d . . . . .
C17 C 0.11218(5) 0.49746(18) 0.08687(7) 0.0245(2) Uani 1 1 d . . . . .
H17A H 0.095393 0.368181 0.080061 0.029 Uiso 1 1 calc R U . . .
H17B H 0.135518 0.488014 0.071497 0.029 Uiso 1 1 calc R U . . .
C18 C 0.06355(6) 0.6435(2) 0.03375(7) 0.0294(3) Uani 1 1 d . . . . .
H18A H 0.037464 0.603885 -0.023824 0.044 Uiso 1 1 calc R U . . .
H18B H 0.040725 0.651341 0.049435 0.044 Uiso 1 1 calc R U . . .
H18C H 0.080686 0.770681 0.040905 0.044 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 C9 1.2031(16) . ?
O2 C9 1.3206(15) . ?
O2 C10 1.4950(15) . ?
O3 C16 1.2066(14) . ?
O4 C16 1.3358(13) . ?
O4 C17 1.4603(13) . ?
N1 C8 1.1460(16) . ?
N2 C15 1.1435(16) . ?
C1 C2 1.4875(15) . ?
C1 C6 1.4887(16) . ?
C1 C7 1.5328(15) . ?
C1 H1A 0.968(15) . ?
C2 C3 1.4852(15) . ?
C2 C14 1.5295(14) . ?
C2 H2A 0.972(16) . ?
C3 C4 1.4826(15) . ?
C3 C14 1.5608(15) . ?
C3 H3A 0.972(16) . ?
C4 C5 1.3292(17) . ?
C4 H4A 0.9500 . ?
C5 C6 1.4805(16) . ?
C5 H5A 0.9500 . ?
C6 C7 1.5573(15) . ?
C6 H6A 0.962(17) . ?
C7 C8 1.4437(15) . ?
C7 C9 1.5040(15) . ?
C10 C11 1.5053(19) . ?
C10 C13 1.510(3) . ?
C10 C12 1.498(3) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.4440(15) . ?
C14 C16 1.4940(15) . ?
C17 C18 1.4994(17) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?

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 O2 C10 121.18(10) . . ?
C16 O4 C17 115.16(9) . . ?
C2 C1 C6 118.82(9) . . ?
C2 C1 C7 118.46(9) . . ?
C6 C1 C7 62.03(7) . . ?
C2 C1 H1A 115.7(9) . . ?
C6 C1 H1A 118.1(9) . . ?
C7 C1 H1A 113.0(9) . . ?
C1 C2 C3 118.58(9) . . ?
C1 C2 C14 117.58(9) . . ?
C3 C2 C14 62.34(7) . . ?
C1 C2 H2A 117.3(9) . . ?
C3 C2 H2A 116.7(9) . . ?
C14 C2 H2A 112.6(9) . . ?
C4 C3 C2 118.99(9) . . ?
C4 C3 C14 117.85(9) . . ?
C2 C3 C14 60.22(7) . . ?
C4 C3 H3A 119.7(9) . . ?
C2 C3 H3A 114.8(9) . . ?
C14 C3 H3A 111.0(9) . . ?
C5 C4 C3 122.40(10) . . ?
C5 C4 H4A 118.8 . . ?
C3 C4 H4A 118.8 . . ?
C4 C5 C6 122.35(10) . . ?
C4 C5 H5A 118.8 . . ?
C6 C5 H5A 118.8 . . ?
C5 C6 C1 118.84(10) . . ?
C5 C6 C7 118.24(10) . . ?
C1 C6 C7 60.37(7) . . ?
C5 C6 H6A 118.0(9) . . ?
C1 C6 H6A 117.0(9) . . ?
C7 C6 H6A 111.2(10) . . ?
C8 C7 C9 117.73(10) . . ?
C8 C7 C1 118.07(9) . . ?
C9 C7 C1 115.76(9) . . ?
C8 C7 C6 117.69(9) . . ?
C9 C7 C6 116.25(10) . . ?
C1 C7 C6 57.60(7) . . ?
N1 C8 C7 178.02(15) . . ?
O1 C9 O2 127.39(11) . . ?
O1 C9 C7 122.08(11) . . ?
O2 C9 C7 110.53(10) . . ?
O2 C10 C11 109.54(11) . . ?
O2 C10 C13 101.24(13) . . ?
C11 C10 C13 110.53(17) . . ?
O2 C10 C12 109.71(12) . . ?
C11 C10 C12 113.36(15) . . ?
C13 C10 C12 111.8(2) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C16 118.08(9) . . ?
C15 C14 C2 118.48(9) . . ?
C16 C14 C2 115.65(9) . . ?
C15 C14 C3 117.59(9) . . ?
C16 C14 C3 115.52(9) . . ?
C2 C14 C3 57.44(7) . . ?
N2 C15 C14 177.55(12) . . ?
O3 C16 O4 125.05(10) . . ?
O3 C16 C14 123.05(10) . . ?
O4 C16 C14 111.88(9) . . ?
O4 C17 C18 107.46(10) . . ?
O4 C17 H17A 110.2 . . ?
C18 C17 H17A 110.2 . . ?
O4 C17 H17B 110.2 . . ?
C18 C17 H17B 110.2 . . ?
H17A C17 H17B 108.5 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.75(14) . . . . ?
C7 C1 C2 C3 71.15(13) . . . . ?
C6 C1 C2 C14 71.08(13) . . . . ?
C7 C1 C2 C14 142.98(10) . . . . ?
C1 C2 C3 C4 0.69(15) . . . . ?
C14 C2 C3 C4 -107.35(11) . . . . ?
C1 C2 C3 C14 108.04(11) . . . . ?
C2 C3 C4 C5 -0.88(16) . . . . ?
C14 C3 C4 C5 -70.43(14) . . . . ?
C3 C4 C5 C6 1.10(17) . . . . ?
C4 C5 C6 C1 -1.12(16) . . . . ?
C4 C5 C6 C7 -70.95(15) . . . . ?
C2 C1 C6 C5 0.93(15) . . . . ?
C7 C1 C6 C5 -107.95(11) . . . . ?
C2 C1 C6 C7 108.88(11) . . . . ?
C2 C1 C7 C8 -2.87(15) . . . . ?
C6 C1 C7 C8 106.58(11) . . . . ?
C2 C1 C7 C9 144.56(10) . . . . ?
C6 C1 C7 C9 -105.98(11) . . . . ?
C2 C1 C7 C6 -109.45(11) . . . . ?
C5 C6 C7 C8 1.70(15) . . . . ?
C1 C6 C7 C8 -107.23(11) . . . . ?
C5 C6 C7 C9 -145.94(11) . . . . ?
C1 C6 C7 C9 105.13(11) . . . . ?
C5 C6 C7 C1 108.94(11) . . . . ?
C10 O2 C9 O1 -1.2(2) . . . . ?
C10 O2 C9 C7 179.25(11) . . . . ?
C8 C7 C9 O1 170.21(12) . . . . ?
C1 C7 C9 O1 22.66(17) . . . . ?
C6 C7 C9 O1 -42.16(17) . . . . ?
C8 C7 C9 O2 -10.22(15) . . . . ?
C1 C7 C9 O2 -157.78(10) . . . . ?
C6 C7 C9 O2 137.40(10) . . . . ?
C9 O2 C10 C11 -61.23(17) . . . . ?
C9 O2 C10 C13 -177.97(18) . . . . ?
C9 O2 C10 C12 63.81(18) . . . . ?
C1 C2 C14 C15 -3.43(14) . . . . ?
C3 C2 C14 C15 106.19(11) . . . . ?
C1 C2 C14 C16 145.29(10) . . . . ?
C3 C2 C14 C16 -105.10(10) . . . . ?
C1 C2 C14 C3 -109.61(11) . . . . ?
C4 C3 C14 C15 1.48(14) . . . . ?
C2 C3 C14 C15 -107.74(11) . . . . ?
C4 C3 C14 C16 -145.46(10) . . . . ?
C2 C3 C14 C16 105.32(10) . . . . ?
C4 C3 C14 C2 109.22(11) . . . . ?
C17 O4 C16 O3 -1.69(16) . . . . ?
C17 O4 C16 C14 179.83(9) . . . . ?
C15 C14 C16 O3 172.06(11) . . . . ?
C2 C14 C16 O3 23.22(15) . . . . ?
C3 C14 C16 O3 -41.17(15) . . . . ?
C15 C14 C16 O4 -9.42(14) . . . . ?
C2 C14 C16 O4 -158.27(9) . . . . ?
C3 C14 C16 O4 137.35(10) . . . . ?
C16 O4 C17 C18 172.51(10) . . . . ?

_refine_diff_density_max         0.300
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.047

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_h-m   C2/c
_symmetry_int_tables_number      ?
_chemical_absolute_configuration ?

####################################################################### 
# 
# 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_Zhu94
_database_code_depnum_ccdc_archive 'CCDC 2348853'
loop_
_audit_author_name
_audit_author_address
'Dao-Wen Luo'
;the Instrument Centre of National Chung Hsing University
Taiwan
;
_audit_update_record             
;
2024-04-17 deposited with the CCDC.	2024-06-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C22 H20 N2 O3'
_chemical_formula_sum            'C22 H20 N2 O3'
_chemical_melting_point          ?

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            white
_diffrn_ambient_temperature      150(2)
_chemical_formula_weight         360.40

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      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                   9.3006(8)
_cell_length_b                   17.4882(15)
_cell_length_c                   12.2650(11)
_cell_angle_alpha                90
_cell_angle_beta                 111.591(3)
_cell_angle_gamma                90
_cell_volume                     1854.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9378
_cell_measurement_theta_min      2.627
_cell_measurement_theta_max      27.893
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_F_000             760
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.290
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.087
_shelx_estimated_absorpt_T_min   0.974
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5697
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25042
_diffrn_reflns_av_unetI/netI     0.0459
_diffrn_reflns_av_R_equivalents  0.0674
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.935
_diffrn_reflns_theta_max         27.897
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             4406
_reflns_number_gt                3587
_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       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V7.34A (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT V7.34A (Bruker AXS, 2006)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL
_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)+(0.1148P)²+0.6328P] 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_number_reflns         4406
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0701
_refine_ls_R_factor_gt           0.0561
_refine_ls_wR_factor_ref         0.1799
_refine_ls_wR_factor_gt          0.1644
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.000
_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 1.04460(14) 0.11772(9) 0.45798(11) 0.0331(3) Uani 1 1 d . . . . .
O2 O 0.50116(13) 0.21012(7) -0.09635(10) 0.0253(3) Uani 1 1 d . . . . .
O3 O 0.69458(14) 0.25689(8) -0.14770(11) 0.0284(3) Uani 1 1 d . . . . .
N1 N 0.5700(2) -0.00375(11) 0.23226(14) 0.0355(4) Uani 1 1 d . . . . .
N2 N 1.03452(18) 0.15870(11) 0.01983(15) 0.0340(4) Uani 1 1 d . . . . .
C1 C 0.8804(2) 0.14571(10) 0.60359(15) 0.0262(4) Uani 1 1 d . . . . .
H1A H 0.953125 0.183576 0.602463 0.031 Uiso 1 1 calc R U . . .
C2 C 0.8150(2) 0.14868(11) 0.68796(17) 0.0314(4) Uani 1 1 d . . . . .
H2A H 0.840979 0.189122 0.743575 0.038 Uiso 1 1 calc R U . . .
C3 C 0.7114(2) 0.09261(11) 0.69147(16) 0.0297(4) Uani 1 1 d . . . . .
H3A H 0.666299 0.094667 0.749444 0.036 Uiso 1 1 calc R U . . .
C4 C 0.6737(2) 0.03367(10) 0.61056(15) 0.0265(4) Uani 1 1 d . . . . .
H4A H 0.603947 -0.005105 0.614013 0.032 Uiso 1 1 calc R U . . .
C5 C 0.73711(19) 0.03082(10) 0.52439(14) 0.0234(4) Uani 1 1 d . . . . .
H5A H 0.710150 -0.009566 0.468677 0.028 Uiso 1 1 calc R U . . .
C6 C 0.84033(18) 0.08727(9) 0.51970(13) 0.0207(3) Uani 1 1 d . . . . .
C7 C 0.91643(19) 0.09073(10) 0.43182(14) 0.0226(3) Uani 1 1 d . . . . .
C8 C 0.83213(18) 0.06750(10) 0.30559(14) 0.0209(3) Uani 1 1 d . . . . .
C9 C 0.6860(2) 0.02760(10) 0.26732(14) 0.0248(4) Uani 1 1 d . . . . .
C10 C 0.84885(18) 0.12748(9) 0.21853(13) 0.0194(3) Uani 1 1 d . . . . .
H10A H 0.912022 0.173627 0.254449 0.023 Uiso 1 1 calc R U . . .
C11 C 0.93535(19) 0.05490(10) 0.23219(15) 0.0233(4) Uani 1 1 d . . . . .
H11A H 1.049234 0.058702 0.277006 0.028 Uiso 1 1 calc R U . . .
C12 C 0.8880(2) -0.00131(10) 0.13451(16) 0.0272(4) Uani 1 1 d . . . . .
H12A H 0.943671 -0.047915 0.143770 0.033 Uiso 1 1 calc R U . . .
C13 C 0.7697(2) 0.01160(10) 0.03429(16) 0.0265(4) Uani 1 1 d . . . . .
H13A H 0.745444 -0.025536 -0.026360 0.032 Uiso 1 1 calc R U . . .
C14 C 0.67485(19) 0.08208(9) 0.01442(14) 0.0213(3) Uani 1 1 d . . . . .
H14A H 0.562308 0.075421 -0.033137 0.026 Uiso 1 1 calc R U . . .
C15 C 0.71268(18) 0.14106(9) 0.10797(14) 0.0191(3) Uani 1 1 d . . . . .
H15A H 0.622918 0.168389 0.116437 0.023 Uiso 1 1 calc R U . . .
C16 C 0.74661(18) 0.15942(9) -0.00283(14) 0.0209(3) Uani 1 1 d . . . . .
C17 C 0.9068(2) 0.15993(10) 0.00833(14) 0.0244(4) Uani 1 1 d . . . . .
C18 C 0.64579(19) 0.21526(9) -0.09109(14) 0.0214(3) Uani 1 1 d . . . . .
C19 C 0.3716(2) 0.25036(10) -0.18829(16) 0.0258(4) Uani 1 1 d . . . . .
C20 C 0.2331(2) 0.22397(14) -0.16153(19) 0.0389(5) Uani 1 1 d . . . . .
H20A H 0.138983 0.247210 -0.217526 0.058 Uiso 1 1 calc R U . . .
H20B H 0.224854 0.168154 -0.168020 0.058 Uiso 1 1 calc R U . . .
H20C H 0.245725 0.239448 -0.081732 0.058 Uiso 1 1 calc R U . . .
C21 C 0.3618(2) 0.22310(14) -0.30769(17) 0.0391(5) Uani 1 1 d . . . . .
H21A H 0.276734 0.249402 -0.368532 0.059 Uiso 1 1 calc R U . . .
H21B H 0.459274 0.234378 -0.318013 0.059 Uiso 1 1 calc R U . . .
H21C H 0.343240 0.167824 -0.313979 0.059 Uiso 1 1 calc R U . . .
C22 C 0.3939(3) 0.33599(12) -0.1714(3) 0.0499(6) Uani 1 1 d . . . . .
H22A H 0.308788 0.362575 -0.231835 0.075 Uiso 1 1 calc R U . . .
H22B H 0.395275 0.350098 -0.093729 0.075 Uiso 1 1 calc R U . . .
H22C H 0.492227 0.350680 -0.177811 0.075 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 C7 1.210(2) . ?
O2 C18 1.326(2) . ?
O2 C19 1.490(2) . ?
O3 C18 1.204(2) . ?
N1 C9 1.144(2) . ?
N2 C17 1.144(2) . ?
C1 C2 1.381(3) . ?
C1 C6 1.400(2) . ?
C1 H1A 0.9500 . ?
C2 C3 1.386(3) . ?
C2 H2A 0.9500 . ?
C3 C4 1.384(3) . ?
C3 H3A 0.9500 . ?
C4 C5 1.388(2) . ?
C4 H4A 0.9500 . ?
C5 C6 1.393(2) . ?
C5 H5A 0.9500 . ?
C6 C7 1.493(2) . ?
C7 C8 1.511(2) . ?
C8 C9 1.444(2) . ?
C8 C10 1.545(2) . ?
C8 C11 1.555(2) . ?
C10 C11 1.479(2) . ?
C10 C15 1.495(2) . ?
C10 H10A 1.0000 . ?
C11 C12 1.486(2) . ?
C11 H11A 1.0000 . ?
C12 C13 1.333(3) . ?
C12 H12A 0.9500 . ?
C13 C14 1.483(2) . ?
C13 H13A 0.9500 . ?
C14 C15 1.486(2) . ?
C14 C16 1.557(2) . ?
C14 H14A 1.0000 . ?
C15 C16 1.538(2) . ?
C15 H15A 1.0000 . ?
C16 C17 1.445(2) . ?
C16 C18 1.503(2) . ?
C19 C21 1.511(3) . ?
C19 C22 1.516(3) . ?
C19 C20 1.513(3) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?

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
C18 O2 C19 121.91(13) . . ?
C2 C1 C6 120.43(16) . . ?
C2 C1 H1A 119.8 . . ?
C6 C1 H1A 119.8 . . ?
C1 C2 C3 119.97(17) . . ?
C1 C2 H2A 120.0 . . ?
C3 C2 H2A 120.0 . . ?
C4 C3 C2 120.03(17) . . ?
C4 C3 H3A 120.0 . . ?
C2 C3 H3A 120.0 . . ?
C3 C4 C5 120.42(17) . . ?
C3 C4 H4A 119.8 . . ?
C5 C4 H4A 119.8 . . ?
C6 C5 C4 119.90(15) . . ?
C6 C5 H5A 120.0 . . ?
C4 C5 H5A 120.0 . . ?
C5 C6 C1 119.23(15) . . ?
C5 C6 C7 125.15(15) . . ?
C1 C6 C7 115.60(15) . . ?
O1 C7 C6 120.46(15) . . ?
O1 C7 C8 117.74(15) . . ?
C6 C7 C8 121.59(14) . . ?
C9 C8 C7 122.31(14) . . ?
C9 C8 C10 115.18(14) . . ?
C7 C8 C10 112.28(14) . . ?
C9 C8 C11 116.82(14) . . ?
C7 C8 C11 115.67(13) . . ?
C10 C8 C11 57.00(10) . . ?
N1 C9 C8 177.13(18) . . ?
C11 C10 C15 118.88(14) . . ?
C11 C10 C8 61.83(11) . . ?
C15 C10 C8 117.88(13) . . ?
C11 C10 H10A 115.8 . . ?
C15 C10 H10A 115.8 . . ?
C8 C10 H10A 115.8 . . ?
C12 C11 C10 119.27(14) . . ?
C12 C11 C8 119.84(15) . . ?
C10 C11 C8 61.18(11) . . ?
C12 C11 H11A 115.3 . . ?
C10 C11 H11A 115.3 . . ?
C8 C11 H11A 115.3 . . ?
C13 C12 C11 122.07(16) . . ?
C13 C12 H12A 119.0 . . ?
C11 C12 H12A 119.0 . . ?
C12 C13 C14 122.11(15) . . ?
C12 C13 H13A 118.9 . . ?
C14 C13 H13A 118.9 . . ?
C15 C14 C13 119.52(14) . . ?
C15 C14 C16 60.67(10) . . ?
C13 C14 C16 119.05(14) . . ?
C15 C14 H14A 115.5 . . ?
C13 C14 H14A 115.5 . . ?
C16 C14 H14A 115.5 . . ?
C14 C15 C10 118.11(14) . . ?
C14 C15 C16 61.96(10) . . ?
C10 C15 C16 116.99(13) . . ?
C14 C15 H15A 116.3 . . ?
C10 C15 H15A 116.3 . . ?
C16 C15 H15A 116.3 . . ?
C17 C16 C18 114.37(14) . . ?
C17 C16 C15 117.21(14) . . ?
C18 C16 C15 119.72(14) . . ?
C17 C16 C14 118.10(14) . . ?
C18 C16 C14 118.52(13) . . ?
C15 C16 C14 57.37(10) . . ?
N2 C17 C16 177.9(2) . . ?
O3 C18 O2 127.15(16) . . ?
O3 C18 C16 122.73(15) . . ?
O2 C18 C16 110.12(13) . . ?
O2 C19 C21 109.13(15) . . ?
O2 C19 C22 109.35(15) . . ?
C21 C19 C22 113.60(19) . . ?
O2 C19 C20 102.00(14) . . ?
C21 C19 C20 111.21(17) . . ?
C22 C19 C20 110.90(19) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 1.4(3) . . . . ?
C1 C2 C3 C4 0.1(3) . . . . ?
C2 C3 C4 C5 -1.0(3) . . . . ?
C3 C4 C5 C6 0.5(3) . . . . ?
C4 C5 C6 C1 0.9(2) . . . . ?
C4 C5 C6 C7 179.95(15) . . . . ?
C2 C1 C6 C5 -1.9(3) . . . . ?
C2 C1 C6 C7 179.01(16) . . . . ?
C5 C6 C7 O1 -148.36(18) . . . . ?
C1 C6 C7 O1 30.7(2) . . . . ?
C5 C6 C7 C8 37.1(2) . . . . ?
C1 C6 C7 C8 -143.86(16) . . . . ?
O1 C7 C8 C9 173.44(17) . . . . ?
C6 C7 C8 C9 -11.9(3) . . . . ?
O1 C7 C8 C10 -43.1(2) . . . . ?
C6 C7 C8 C10 131.58(16) . . . . ?
O1 C7 C8 C11 19.7(2) . . . . ?
C6 C7 C8 C11 -165.56(15) . . . . ?
C9 C8 C10 C11 -106.81(16) . . . . ?
C7 C8 C10 C11 106.99(15) . . . . ?
C9 C8 C10 C15 2.9(2) . . . . ?
C7 C8 C10 C15 -143.35(14) . . . . ?
C11 C8 C10 C15 109.66(16) . . . . ?
C15 C10 C11 C12 2.0(2) . . . . ?
C8 C10 C11 C12 110.04(17) . . . . ?
C15 C10 C11 C8 -108.08(16) . . . . ?
C9 C8 C11 C12 -5.2(2) . . . . ?
C7 C8 C11 C12 149.95(15) . . . . ?
C10 C8 C11 C12 -109.13(17) . . . . ?
C9 C8 C11 C10 103.90(16) . . . . ?
C7 C8 C11 C10 -100.92(16) . . . . ?
C10 C11 C12 C13 0.2(3) . . . . ?
C8 C11 C12 C13 71.8(2) . . . . ?
C11 C12 C13 C14 -1.5(3) . . . . ?
C12 C13 C14 C15 0.7(3) . . . . ?
C12 C13 C14 C16 71.5(2) . . . . ?
C13 C14 C15 C10 1.4(2) . . . . ?
C16 C14 C15 C10 -107.37(15) . . . . ?
C13 C14 C15 C16 108.78(17) . . . . ?
C11 C10 C15 C14 -2.7(2) . . . . ?
C8 C10 C15 C14 -74.11(19) . . . . ?
C11 C10 C15 C16 -73.64(19) . . . . ?
C8 C10 C15 C16 -145.08(14) . . . . ?
C14 C15 C16 C17 -107.44(16) . . . . ?
C10 C15 C16 C17 1.7(2) . . . . ?
C14 C15 C16 C18 106.70(16) . . . . ?
C10 C15 C16 C18 -144.17(15) . . . . ?
C10 C15 C16 C14 109.13(16) . . . . ?
C15 C14 C16 C17 105.87(16) . . . . ?
C13 C14 C16 C17 -3.7(2) . . . . ?
C15 C14 C16 C18 -108.79(16) . . . . ?
C13 C14 C16 C18 141.68(15) . . . . ?
C13 C14 C16 C15 -109.54(16) . . . . ?
C19 O2 C18 O3 8.3(3) . . . . ?
C19 O2 C18 C16 -170.93(14) . . . . ?
C17 C16 C18 O3 0.0(2) . . . . ?
C15 C16 C18 O3 146.78(16) . . . . ?
C14 C16 C18 O3 -146.57(17) . . . . ?
C17 C16 C18 O2 179.24(14) . . . . ?
C15 C16 C18 O2 -34.0(2) . . . . ?
C14 C16 C18 O2 32.7(2) . . . . ?
C18 O2 C19 C21 59.5(2) . . . . ?
C18 O2 C19 C22 -65.3(2) . . . . ?
C18 O2 C19 C20 177.23(16) . . . . ?

_refine_diff_density_max         0.471
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.069

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_h-m   P2(1)/c
_symmetry_int_tables_number      ?
_chemical_absolute_configuration ?

####################################################################### 
# 
# 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_Zhu74
_database_code_depnum_ccdc_archive 'CCDC 2348856'
loop_
_audit_author_name
_audit_author_address
'Dao-Wen Luo'
;the Instrument Centre of National Chung Hsing University
Taiwan
;
_audit_update_record             
;
2024-04-17 deposited with the CCDC.	2024-06-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C15 H14 N2 O3'
_chemical_formula_sum            'C15 H14 N2 O3'
_chemical_melting_point          ?

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            colourless
_diffrn_ambient_temperature      150(2)
_chemical_formula_weight         270.28

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   11.3162(9)
_cell_length_b                   6.9319(6)
_cell_length_c                   17.3008(12)
_cell_angle_alpha                90
_cell_angle_beta                 100.795(3)
_cell_angle_gamma                90
_cell_volume                     1333.11(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9857
_cell_measurement_theta_min      2.938
_cell_measurement_theta_max      27.881
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_F_000             568
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.170
_exptl_absorpt_coefficient_mu    0.095
_shelx_estimated_absorpt_T_min   0.976
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6958
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            33347
_diffrn_reflns_av_unetI/netI     0.0204
_diffrn_reflns_av_R_equivalents  0.0395
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.370
_diffrn_reflns_theta_max         27.882
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3182
_reflns_number_gt                2953
_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       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V7.34A (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT V7.34A (Bruker AXS, 2006)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL
_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)+(0.0881P)²+1.0321P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3182
_refine_ls_number_parameters     205
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0545
_refine_ls_R_factor_gt           0.0512
_refine_ls_wR_factor_ref         0.1552
_refine_ls_wR_factor_gt          0.1502
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.002
_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 0.39998(12) 0.7046(2) 0.06727(7) 0.0303(3) Uani 1 1 d . . . . .
O2 O 0.60565(11) 0.33810(18) 0.45209(7) 0.0265(3) Uani 1 1 d . . . . .
O3 O 0.79081(11) 0.36114(19) 0.42150(8) 0.0298(3) Uani 1 1 d . . . . .
N1 N 0.23023(14) 0.8018(3) 0.29138(9) 0.0318(4) Uani 1 1 d . . . . .
N2 N 0.81089(14) 0.7576(2) 0.30732(10) 0.0305(4) Uani 1 1 d . . . . .
C1 C 0.50158(13) 0.6509(2) 0.23022(8) 0.0161(3) Uani 1 1 d . . . . .
H1A H 0.524(2) 0.574(3) 0.1914(13) 0.029(5) Uiso 1 1 d . . . . .
C2 C 0.51805(12) 0.5694(2) 0.31133(8) 0.0166(3) Uani 1 1 d . . . . .
H2A H 0.470787 0.450293 0.317409 0.020 Uiso 1 1 calc R U . . .
C3 C 0.53691(13) 0.7051(2) 0.37958(9) 0.0191(3) Uani 1 1 d . . . . .
H3A H 0.5096(17) 0.670(3) 0.4247(12) 0.018(5) Uiso 1 1 d . . . . .
C4 C 0.54026(14) 0.9156(2) 0.36437(10) 0.0220(3) Uani 1 1 d . . . . .
H4A H 0.552473 1.002106 0.407736 0.026 Uiso 1 1 calc R U . . .
C5 C 0.52672(13) 0.9865(2) 0.29217(10) 0.0216(3) Uani 1 1 d . . . . .
H5A H 0.530275 1.122380 0.285718 0.026 Uiso 1 1 calc R U . . .
C6 C 0.50632(13) 0.8633(2) 0.22115(9) 0.0179(3) Uani 1 1 d . . . . .
H6A H 0.5297(19) 0.903(3) 0.1745(13) 0.026(5) Uiso 1 1 d . . . . .
C7 C 0.38307(13) 0.7569(2) 0.19898(9) 0.0161(3) Uani 1 1 d . . . . .
C8 C 0.29856(14) 0.7810(2) 0.25113(9) 0.0202(3) Uani 1 1 d . . . . .
C9 C 0.33291(14) 0.7343(2) 0.11237(9) 0.0194(3) Uani 1 1 d . . . . .
C10 C 0.19971(17) 0.7513(3) 0.08625(11) 0.0334(4) Uani 1 1 d . . . . .
H10A H 0.162(3) 0.669(5) 0.1170(18) 0.057(8) Uiso 1 1 d . . . . .
H10B H 0.187(3) 0.727(5) 0.0276(19) 0.060(9) Uiso 1 1 d . . . . .
H10C H 0.182(3) 0.909(6) 0.098(2) 0.086(11) Uiso 1 1 d . . . . .
C11 C 0.64405(13) 0.5812(2) 0.36352(9) 0.0185(3) Uani 1 1 d . . . . .
C12 C 0.73819(14) 0.6765(2) 0.33230(10) 0.0221(3) Uani 1 1 d . . . . .
C13 C 0.67712(14) 0.4131(2) 0.41798(9) 0.0203(3) Uani 1 1 d . . . . .
C14 C 0.83649(16) 0.2010(3) 0.47453(12) 0.0319(4) Uani 1 1 d . . . . .
H14A H 0.887703 0.115541 0.448883 0.038 Uiso 1 1 calc R U . . .
H14B H 0.768329 0.123967 0.486278 0.038 Uiso 1 1 calc R U . . .
C15 C 0.9081(2) 0.2803(3) 0.54905(11) 0.0338(4) Uani 1 1 d . . . . .
H15A H 0.938596 0.173852 0.584478 0.051 Uiso 1 1 calc R U . . .
H15B H 0.975836 0.355394 0.537146 0.051 Uiso 1 1 calc R U . . .
H15C H 0.856766 0.363798 0.574445 0.051 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 C9 1.204(2) . ?
O2 C13 1.205(2) . ?
O3 C13 1.3263(19) . ?
O3 C14 1.471(2) . ?
N1 C8 1.143(2) . ?
N2 C12 1.146(2) . ?
C1 C6 1.482(2) . ?
C1 C2 1.492(2) . ?
C1 C7 1.536(2) . ?
C1 H1A 0.93(2) . ?
C2 C3 1.493(2) . ?
C2 C11 1.5403(19) . ?
C2 H2A 1.0000 . ?
C3 C4 1.485(2) . ?
C3 C11 1.552(2) . ?
C3 H3A 0.92(2) . ?
C4 C5 1.324(2) . ?
C4 H4A 0.9500 . ?
C5 C6 1.479(2) . ?
C5 H5A 0.9500 . ?
C6 C7 1.561(2) . ?
C6 H6A 0.94(2) . ?
C7 C8 1.442(2) . ?
C7 C9 1.508(2) . ?
C9 C10 1.495(2) . ?
C10 H10A 0.94(3) . ?
C10 H10B 1.01(3) . ?
C10 H10C 1.14(4) . ?
C11 C12 1.442(2) . ?
C11 C13 1.501(2) . ?
C14 C15 1.493(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?

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
C13 O3 C14 117.25(13) . . ?
C6 C1 C2 118.36(13) . . ?
C6 C1 C7 62.26(9) . . ?
C2 C1 C7 117.33(12) . . ?
C6 C1 H1A 118.3(14) . . ?
C2 C1 H1A 117.2(14) . . ?
C7 C1 H1A 111.2(14) . . ?
C3 C2 C1 118.66(13) . . ?
C3 C2 C11 61.54(10) . . ?
C1 C2 C11 118.05(12) . . ?
C3 C2 H2A 115.9 . . ?
C1 C2 H2A 115.9 . . ?
C11 C2 H2A 115.9 . . ?
C4 C3 C2 118.91(13) . . ?
C4 C3 C11 117.72(13) . . ?
C2 C3 C11 60.72(9) . . ?
C4 C3 H3A 115.7(13) . . ?
C2 C3 H3A 118.6(13) . . ?
C11 C3 H3A 113.6(13) . . ?
C5 C4 C3 121.99(14) . . ?
C5 C4 H4A 119.0 . . ?
C3 C4 H4A 119.0 . . ?
C4 C5 C6 122.81(15) . . ?
C4 C5 H5A 118.6 . . ?
C6 C5 H5A 118.6 . . ?
C5 C6 C1 119.27(13) . . ?
C5 C6 C7 118.07(12) . . ?
C1 C6 C7 60.55(9) . . ?
C5 C6 H6A 121.3(14) . . ?
C1 C6 H6A 114.0(14) . . ?
C7 C6 H6A 108.1(13) . . ?
C8 C7 C9 117.61(13) . . ?
C8 C7 C1 118.23(13) . . ?
C9 C7 C1 116.20(13) . . ?
C8 C7 C6 117.28(13) . . ?
C9 C7 C6 116.48(13) . . ?
C1 C7 C6 57.20(9) . . ?
N1 C8 C7 178.74(17) . . ?
O1 C9 C10 122.68(15) . . ?
O1 C9 C7 119.75(14) . . ?
C10 C9 C7 117.57(14) . . ?
C9 C10 H10A 108.6(19) . . ?
C9 C10 H10B 103.5(18) . . ?
H10A C10 H10B 118(3) . . ?
C9 C10 H10C 102.9(19) . . ?
H10A C10 H10C 112(2) . . ?
H10B C10 H10C 110(2) . . ?
C12 C11 C13 118.42(13) . . ?
C12 C11 C2 118.19(13) . . ?
C13 C11 C2 114.91(13) . . ?
C12 C11 C3 118.05(13) . . ?
C13 C11 C3 115.35(13) . . ?
C2 C11 C3 57.74(9) . . ?
N2 C12 C11 177.80(17) . . ?
O2 C13 O3 126.51(15) . . ?
O2 C13 C11 122.07(14) . . ?
O3 C13 C11 111.41(13) . . ?
O3 C14 C15 109.34(16) . . ?
O3 C14 H14A 109.8 . . ?
C15 C14 H14A 109.8 . . ?
O3 C14 H14B 109.8 . . ?
C15 C14 H14B 109.8 . . ?
H14A C14 H14B 108.3 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.80(19) . . . . ?
C7 C1 C2 C3 -70.75(17) . . . . ?
C6 C1 C2 C11 -70.29(17) . . . . ?
C7 C1 C2 C11 -141.84(13) . . . . ?
C1 C2 C3 C4 -0.82(19) . . . . ?
C11 C2 C3 C4 107.43(15) . . . . ?
C1 C2 C3 C11 -108.26(14) . . . . ?
C2 C3 C4 C5 0.2(2) . . . . ?
C11 C3 C4 C5 70.2(2) . . . . ?
C3 C4 C5 C6 0.5(2) . . . . ?
C4 C5 C6 C1 -0.5(2) . . . . ?
C4 C5 C6 C7 69.61(19) . . . . ?
C2 C1 C6 C5 -0.16(19) . . . . ?
C7 C1 C6 C5 107.64(15) . . . . ?
C2 C1 C6 C7 -107.79(14) . . . . ?
C6 C1 C7 C8 -105.83(15) . . . . ?
C2 C1 C7 C8 3.6(2) . . . . ?
C6 C1 C7 C9 105.91(14) . . . . ?
C2 C1 C7 C9 -144.68(14) . . . . ?
C2 C1 C7 C6 109.41(15) . . . . ?
C5 C6 C7 C8 -2.1(2) . . . . ?
C1 C6 C7 C8 107.51(15) . . . . ?
C5 C6 C7 C9 145.00(14) . . . . ?
C1 C6 C7 C9 -105.41(14) . . . . ?
C5 C6 C7 C1 -109.59(15) . . . . ?
C8 C7 C9 O1 -176.46(15) . . . . ?
C1 C7 C9 O1 -28.0(2) . . . . ?
C6 C7 C9 O1 36.6(2) . . . . ?
C8 C7 C9 C10 3.9(2) . . . . ?
C1 C7 C9 C10 152.32(15) . . . . ?
C6 C7 C9 C10 -143.11(15) . . . . ?
C3 C2 C11 C12 -107.01(16) . . . . ?
C1 C2 C11 C12 2.2(2) . . . . ?
C3 C2 C11 C13 105.37(15) . . . . ?
C1 C2 C11 C13 -145.40(14) . . . . ?
C1 C2 C11 C3 109.23(15) . . . . ?
C4 C3 C11 C12 -2.1(2) . . . . ?
C2 C3 C11 C12 107.26(15) . . . . ?
C4 C3 C11 C13 146.04(14) . . . . ?
C2 C3 C11 C13 -104.60(14) . . . . ?
C4 C3 C11 C2 -109.35(15) . . . . ?
C14 O3 C13 O2 -2.6(3) . . . . ?
C14 O3 C13 C11 178.36(14) . . . . ?
C12 C11 C13 O2 172.85(15) . . . . ?
C2 C11 C13 O2 -39.6(2) . . . . ?
C3 C11 C13 O2 24.8(2) . . . . ?
C12 C11 C13 O3 -8.0(2) . . . . ?
C2 C11 C13 O3 139.50(14) . . . . ?
C3 C11 C13 O3 -156.04(14) . . . . ?
C13 O3 C14 C15 -100.49(19) . . . . ?

_refine_diff_density_max         0.600
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.058

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_h-m   P2(1)/n
_symmetry_int_tables_number      ?
_chemical_absolute_configuration ?

