# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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. 
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data_r20210103b
_database_code_depnum_ccdc_archive 'CCDC 2298279'
loop_
_audit_author_name
_audit_author_address
'Liu Xiaoyu'
;Nankai University
China
;
_audit_update_record             
;
2023-09-29 deposited with the CCDC.	2023-11-28 downloaded from the CCDC.
;
_audit_creation_date             2021-01-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H15 N O4'
_chemical_formula_sum            'C18 H15 N O4'
_chemical_formula_weight         309.31
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   4.6598(3)
_cell_length_b                   12.6674(15)
_cell_length_c                   13.5783(16)
_cell_angle_alpha                115.794(11)
_cell_angle_beta                 93.082(7)
_cell_angle_gamma                94.546(7)
_cell_volume                     715.88(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2638
_cell_measurement_temperature    113.15
_cell_measurement_theta_max      32.2350
_cell_measurement_theta_min      1.8230
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72745
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             324
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0515
_diffrn_reflns_av_unetI/netI     0.0639
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7528
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         1.837
_diffrn_ambient_temperature      113.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -115.00  65.00   1.00    3.00    --  -25.00  45.00   0.00  180
  2  ω   -115.00  65.00   1.00    3.00    --  -25.00  45.00  90.00  180
  3  ω   -115.00  65.00   1.00    3.00    --  -25.00  45.00 180.00  180
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Rigaku Saturn 70'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0282975000
_diffrn_orient_matrix_UB_12      -0.0103785000
_diffrn_orient_matrix_UB_13      -0.0555098000
_diffrn_orient_matrix_UB_21      0.0019294000
_diffrn_orient_matrix_UB_22      -0.0614305000
_diffrn_orient_matrix_UB_23      -0.0172812000
_diffrn_orient_matrix_UB_31      -0.1507950000
_diffrn_orient_matrix_UB_32      -0.0061112000
_diffrn_orient_matrix_UB_33      0.0043620000
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'rotating anode'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2057
_reflns_number_total             2915
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.618
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.094
_refine_ls_extinction_coef       0.035(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         2915
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1115
_refine_ls_R_factor_gt           0.0834
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1444P)²+0.3654P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2180
_refine_ls_wR_factor_ref         0.2424
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C13(H13), C14(H14), C16(H16), C17(H17)
2.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_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
O1 O 0.2800(5) 0.4047(2) 0.39831(19) 0.0323(6) Uani 1 1 d . . . . .
O2 O 0.6055(5) 0.7881(2) 0.5799(2) 0.0387(7) Uani 1 1 d . . . . .
H2 H 0.616040 0.728391 0.591299 0.058 Uiso 1 1 calc GR . . . .
O3 O 0.3974(5) 0.8172(2) 0.43873(18) 0.0322(6) Uani 1 1 d . . . . .
O4 O 0.9996(6) 0.9501(2) 0.09552(19) 0.0354(6) Uani 1 1 d . . . . .
N1 N 0.3540(6) 0.5787(2) 0.3836(2) 0.0259(6) Uani 1 1 d . . . . .
C1 C 0.3897(7) 0.4643(3) 0.3547(3) 0.0262(7) Uani 1 1 d . . . . .
C2 C 0.5760(6) 0.4307(3) 0.2639(3) 0.0250(7) Uani 1 1 d . . . . .
C3 C 0.6871(7) 0.3248(3) 0.2078(3) 0.0305(8) Uani 1 1 d . . . . .
H3 H 0.643050 0.260306 0.224554 0.037 Uiso 1 1 calc R . . . .
C4 C 0.8643(8) 0.3154(3) 0.1265(3) 0.0332(8) Uani 1 1 d . . . . .
H4 H 0.941385 0.243341 0.085828 0.040 Uiso 1 1 calc R . . . .
C5 C 0.9296(7) 0.4116(3) 0.1043(3) 0.0317(8) Uani 1 1 d . . . . .
H5 H 1.052476 0.403725 0.048434 0.038 Uiso 1 1 calc R . . . .
C6 C 0.8215(7) 0.5184(3) 0.1608(3) 0.0274(7) Uani 1 1 d . . . . .
H6 H 0.869957 0.583443 0.145145 0.033 Uiso 1 1 calc R . . . .
C7 C 0.6385(7) 0.5273(3) 0.2418(3) 0.0259(7) Uani 1 1 d . . . . .
C8 C 0.4962(7) 0.6242(3) 0.3195(2) 0.0253(7) Uani 1 1 d . . . . .
C9 C 0.1869(7) 0.6532(3) 0.4688(3) 0.0286(8) Uani 1 1 d . . . . .
H9A H 0.166609 0.623154 0.524586 0.034 Uiso 1 1 calc R . . . .
H9B H -0.008826 0.653332 0.436709 0.034 Uiso 1 1 calc R . . . .
C10 C 0.3441(8) 0.7768(3) 0.5213(3) 0.0310(8) Uani 1 1 d . . . . .
H10 H 0.216535 0.830268 0.572989 0.037 Uiso 1 1 calc R . . . .
C11 C 0.5076(7) 0.7402(3) 0.3456(3) 0.0265(7) Uani 1 1 d . . . . .
C12 C 0.6336(7) 0.7976(3) 0.2818(3) 0.0272(7) Uani 1 1 d . . . . .
C13 C 0.8391(8) 0.8951(3) 0.3329(3) 0.0308(8) Uani 1 1 d . . . . .
H13 H 0.891726 0.926015 0.409733 0.037 Uiso 1 1 calc R . . . .
C14 C 0.9693(8) 0.9483(3) 0.2740(3) 0.0294(8) Uani 1 1 d . . . . .
H14 H 1.112957 1.014012 0.309771 0.035 Uiso 1 1 calc R . . . .
C15 C 0.8882(7) 0.9048(3) 0.1620(3) 0.0287(8) Uani 1 1 d . . . . .
C16 C 0.6761(7) 0.8085(3) 0.1102(3) 0.0298(8) Uani 1 1 d . . . . .
H16 H 0.617546 0.779456 0.034031 0.036 Uiso 1 1 calc R . . . .
C17 C 0.5516(7) 0.7558(3) 0.1698(3) 0.0292(8) Uani 1 1 d . . . . .
H17 H 0.408033 0.689980 0.134037 0.035 Uiso 1 1 calc R . . . .
C18 C 1.2126(8) 1.0493(3) 0.1445(3) 0.0350(8) Uani 1 1 d . . . . .
H18A H 1.273699 1.073113 0.088445 0.053 Uiso 1 1 calc GR . . . .
H18B H 1.379707 1.028594 0.176553 0.053 Uiso 1 1 calc GR . . . .
H18C H 1.131535 1.114705 0.202247 0.053 Uiso 1 1 calc GR . . . .


_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 1.243(4) . ?
O2 H2 0.8400 . ?
O2 C10 1.380(4) . ?
O3 C10 1.446(4) . ?
O3 C11 1.375(4) . ?
O4 C15 1.367(4) . ?
O4 C18 1.418(4) . ?
N1 C1 1.353(4) . ?
N1 C8 1.403(4) . ?
N1 C9 1.448(4) . ?
C1 C2 1.473(5) . ?
C2 C3 1.382(5) . ?
C2 C7 1.395(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.383(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.393(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.386(5) . ?
C6 H6 0.9500 . ?
C6 C7 1.398(5) . ?
C7 C8 1.462(5) . ?
C8 C11 1.349(5) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.512(5) . ?
C10 H10 1.0000 . ?
C11 C12 1.469(4) . ?
C12 C13 1.386(5) . ?
C12 C17 1.394(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.386(5) . ?
C14 H14 0.9500 . ?
C14 C15 1.391(5) . ?
C15 C16 1.395(5) . ?
C16 H16 0.9500 . ?
C16 C17 1.377(5) . ?
C17 H17 0.9500 . ?
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
C10 O2 H2 109.5 . . ?
C11 O3 C10 116.9(2) . . ?
C15 O4 C18 117.6(3) . . ?
C1 N1 C8 113.0(3) . . ?
C1 N1 C9 127.4(3) . . ?
C8 N1 C9 119.6(3) . . ?
O1 C1 N1 124.6(3) . . ?
O1 C1 C2 129.9(3) . . ?
N1 C1 C2 105.4(3) . . ?
C3 C2 C1 128.9(3) . . ?
C3 C2 C7 122.3(3) . . ?
C7 C2 C1 108.8(3) . . ?
C2 C3 H3 120.9 . . ?
C2 C3 C4 118.1(3) . . ?
C4 C3 H3 120.9 . . ?
C3 C4 H4 120.0 . . ?
C3 C4 C5 120.0(3) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 118.9 . . ?
C6 C5 C4 122.2(3) . . ?
C6 C5 H5 118.9 . . ?
C5 C6 H6 121.1 . . ?
C5 C6 C7 117.7(3) . . ?
C7 C6 H6 121.1 . . ?
C2 C7 C6 119.6(3) . . ?
C2 C7 C8 107.1(3) . . ?
C6 C7 C8 133.3(3) . . ?
N1 C8 C7 105.7(3) . . ?
C11 C8 N1 120.2(3) . . ?
C11 C8 C7 133.6(3) . . ?
N1 C9 H9A 110.1 . . ?
N1 C9 H9B 110.1 . . ?
N1 C9 C10 108.0(3) . . ?
H9A C9 H9B 108.4 . . ?
C10 C9 H9A 110.1 . . ?
C10 C9 H9B 110.1 . . ?
O2 C10 O3 107.9(3) . . ?
O2 C10 C9 114.4(3) . . ?
O2 C10 H10 108.0 . . ?
O3 C10 C9 110.4(3) . . ?
O3 C10 H10 108.0 . . ?
C9 C10 H10 108.0 . . ?
O3 C11 C12 113.4(3) . . ?
C8 C11 O3 121.0(3) . . ?
C8 C11 C12 125.6(3) . . ?
C13 C12 C11 119.9(3) . . ?
C13 C12 C17 118.8(3) . . ?
C17 C12 C11 121.4(3) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 C12 121.1(3) . . ?
C14 C13 H13 119.5 . . ?
C13 C14 H14 120.2 . . ?
C13 C14 C15 119.6(3) . . ?
C15 C14 H14 120.2 . . ?
O4 C15 C14 124.9(3) . . ?
O4 C15 C16 115.3(3) . . ?
C14 C15 C16 119.8(3) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 C15 119.9(3) . . ?
C17 C16 H16 120.1 . . ?
C12 C17 H17 119.6 . . ?
C16 C17 C12 120.9(3) . . ?
C16 C17 H17 119.6 . . ?
O4 C18 H18A 109.5 . . ?
O4 C18 H18B 109.5 . . ?
O4 C18 H18C 109.5 . . ?
H18A C18 H18B 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
O1 C1 C2 C3 -3.5(6) . . . . ?
O1 C1 C2 C7 178.4(3) . . . . ?
O3 C11 C12 C13 52.5(4) . . . . ?
O3 C11 C12 C17 -127.7(3) . . . . ?
O4 C15 C16 C17 179.5(3) . . . . ?
N1 C1 C2 C3 177.1(3) . . . . ?
N1 C1 C2 C7 -1.0(3) . . . . ?
N1 C8 C11 O3 4.2(5) . . . . ?
N1 C8 C11 C12 -176.0(3) . . . . ?
N1 C9 C10 O2 -67.2(3) . . . . ?
N1 C9 C10 O3 54.7(3) . . . . ?
C1 N1 C8 C7 -0.3(3) . . . . ?
C1 N1 C8 C11 -172.8(3) . . . . ?
C1 N1 C9 C10 144.1(3) . . . . ?
C1 C2 C3 C4 -178.5(3) . . . . ?
C1 C2 C7 C6 177.8(3) . . . . ?
C1 C2 C7 C8 0.9(3) . . . . ?
C2 C3 C4 C5 0.9(5) . . . . ?
C2 C7 C8 N1 -0.4(3) . . . . ?
C2 C7 C8 C11 170.7(3) . . . . ?
C3 C2 C7 C6 -0.5(5) . . . . ?
C3 C2 C7 C8 -177.4(3) . . . . ?
C3 C4 C5 C6 -0.3(5) . . . . ?
C4 C5 C6 C7 -0.7(5) . . . . ?
C5 C6 C7 C2 1.1(4) . . . . ?
C5 C6 C7 C8 177.1(3) . . . . ?
C6 C7 C8 N1 -176.7(3) . . . . ?
C6 C7 C8 C11 -5.6(6) . . . . ?
C7 C2 C3 C4 -0.5(5) . . . . ?
C7 C8 C11 O3 -165.9(3) . . . . ?
C7 C8 C11 C12 13.9(6) . . . . ?
C8 N1 C1 O1 -178.6(3) . . . . ?
C8 N1 C1 C2 0.8(3) . . . . ?
C8 N1 C9 C10 -37.1(4) . . . . ?
C8 C11 C12 C13 -127.3(4) . . . . ?
C8 C11 C12 C17 52.5(5) . . . . ?
C9 N1 C1 O1 0.2(5) . . . . ?
C9 N1 C1 C2 179.6(3) . . . . ?
C9 N1 C8 C7 -179.2(3) . . . . ?
C9 N1 C8 C11 8.2(4) . . . . ?
C10 O3 C11 C8 16.6(4) . . . . ?
C10 O3 C11 C12 -163.2(3) . . . . ?
C11 O3 C10 O2 78.9(3) . . . . ?
C11 O3 C10 C9 -46.7(4) . . . . ?
C11 C12 C13 C14 177.6(3) . . . . ?
C11 C12 C17 C16 -178.5(3) . . . . ?
C12 C13 C14 C15 1.4(5) . . . . ?
C13 C12 C17 C16 1.3(5) . . . . ?
C13 C14 C15 O4 179.6(3) . . . . ?
C13 C14 C15 C16 0.3(5) . . . . ?
C14 C15 C16 C17 -1.1(5) . . . . ?
C15 C16 C17 C12 0.4(5) . . . . ?
C17 C12 C13 C14 -2.1(5) . . . . ?
C18 O4 C15 C14 -0.3(5) . . . . ?
C18 O4 C15 C16 179.0(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.491
_oxdiff_exptl_absorpt_empirical_full_min 0.737
####################################################################### 
# 
# 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_p200907a9
_database_code_depnum_ccdc_archive 'CCDC 2298345'
loop_
_audit_author_name
_audit_author_address
'Liu Xiaoyu'
;Nankai University
China
;
_audit_update_record             
;
2023-09-29 deposited with the CCDC.	2023-11-28 downloaded from the CCDC.
;
_audit_creation_date             2023-06-12
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelxl_version_number           2014-1
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C14 H11 N O2'
_chemical_formula_sum            'C14 H11 N O2'
_chemical_formula_weight         225.24
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_H-M_alt        'P 1 2/n 1'
_space_group_name_Hall           '-P 2yac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z-1/2'

_cell_length_a                   6.6228(5)
_cell_length_b                   8.4131(6)
_cell_length_c                   18.9386(13)
_cell_angle_alpha                90
_cell_angle_beta                 93.381(6)
_cell_angle_gamma                90
_cell_volume                     1053.39(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2235
_cell_measurement_temperature    136.2(3)
_cell_measurement_theta_max      28.6950
_cell_measurement_theta_min      3.8970
_shelx_estimated_absorpt_T_max   0.981
_shelx_estimated_absorpt_T_min   0.910
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85420
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            'light colourless'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.420
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          1
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_av_unetI/netI     0.0378
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            6655
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.499
_diffrn_reflns_theta_min         3.204
_diffrn_ambient_temperature      136.2(3)
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1781
_reflns_number_total             2163
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/1 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.667
_refine_diff_density_min         -0.459
_refine_diff_density_rms         0.121
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1231
_refine_ls_R_factor_gt           0.1122
_refine_ls_restrained_S_all      1.023
_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)+(0.0050P)²+12.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2190
_refine_ls_wR_factor_ref         0.2236
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C4(H4), C1(H1), C2(H2), C3(H3)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
O1 O 0.5092(5) 0.6422(3) 0.28384(16) 0.0130(7) Uani 1 1 d . . . . .
O2 O 0.5312(5) 0.6689(4) 0.39991(17) 0.0182(7) Uani 1 1 d . . . . .
N1 N 0.4800(6) 0.2928(4) 0.1674(2) 0.0141(8) Uani 1 1 d . . . . .
C9 C 0.4946(6) 0.3831(5) 0.2263(2) 0.0123(9) Uani 1 1 d . . . . .
C6 C 0.5245(6) 0.4022(5) 0.3564(2) 0.0125(9) Uani 1 1 d . . . . .
C12 C 0.4814(6) 0.6302(5) 0.1587(2) 0.0126(9) Uani 1 1 d . . . . .
C5 C 0.5097(6) 0.3070(5) 0.2956(2) 0.0099(8) Uani 1 1 d . . . . .
C8 C 0.4948(6) 0.5498(5) 0.2228(2) 0.0094(8) Uani 1 1 d . . . . .
C10 C 0.4655(7) 0.3683(6) 0.1062(2) 0.0163(9) Uani 1 1 d . . . . .
H10 H 0.4543 0.3060 0.0643 0.020 Uiso 1 1 calc R U . . .
C11 C 0.4655(7) 0.5349(5) 0.0987(2) 0.0158(9) Uani 1 1 d . . . . .
H11 H 0.4546 0.5818 0.0530 0.019 Uiso 1 1 calc R U . . .
C4 C 0.5092(7) 0.1407(5) 0.3033(2) 0.0148(9) Uani 1 1 d . . . . .
H4 H 0.5007 0.0744 0.2627 0.018 Uiso 1 1 calc R U . . .
C7 C 0.5223(6) 0.5772(5) 0.3509(2) 0.0101(8) Uani 1 1 d . . . . .
C1 C 0.5364(7) 0.3328(5) 0.4236(2) 0.0137(9) Uani 1 1 d . . . . .
H1 H 0.5450 0.3980 0.4646 0.016 Uiso 1 1 calc R U . . .
C2 C 0.5355(7) 0.1690(6) 0.4302(3) 0.0187(10) Uani 1 1 d . . . . .
H2 H 0.5447 0.1215 0.4758 0.022 Uiso 1 1 calc R U . . .
C13 C 0.4845(7) 0.8098(5) 0.1574(2) 0.0145(9) Uani 1 1 d . . . . .
H13A H 0.6071 0.8468 0.1851 0.017 Uiso 1 1 calc R U . . .
H13B H 0.3656 0.8493 0.1815 0.017 Uiso 1 1 calc R U . . .
C3 C 0.5211(7) 0.0737(5) 0.3700(3) 0.0185(10) Uani 1 1 d . . . . .
H3 H 0.5194 -0.0387 0.3748 0.022 Uiso 1 1 calc R U . . .
C14 C 0.4825(9) 0.8843(6) 0.0840(3) 0.0247(11) Uani 1 1 d . . . . .
H14A H 0.3617 0.8490 0.0560 0.037 Uiso 1 1 calc R U . . .
H14B H 0.6038 0.8514 0.0606 0.037 Uiso 1 1 calc R U . . .
H14C H 0.4806 1.0003 0.0883 0.037 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 C8 1.393(5) . ?
O1 C7 1.381(5) . ?
O2 C7 1.205(5) . ?
N1 C9 1.349(6) . ?
N1 C10 1.320(6) . ?
C9 C5 1.458(6) . ?
C9 C8 1.404(6) . ?
C6 C5 1.402(6) . ?
C6 C7 1.476(6) . ?
C6 C1 1.398(6) . ?
C12 C8 1.388(6) . ?
C12 C11 1.390(6) . ?
C12 C13 1.512(6) . ?
C5 C4 1.407(6) . ?
C10 H10 0.9500 . ?
C10 C11 1.409(6) . ?
C11 H11 0.9500 . ?
C4 H4 0.9500 . ?
C4 C3 1.380(7) . ?
C1 H1 0.9500 . ?
C1 C2 1.384(6) . ?
C2 H2 0.9500 . ?
C2 C3 1.393(7) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.524(6) . ?
C3 H3 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 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
C7 O1 C8 122.7(3) . . ?
C10 N1 C9 117.0(4) . . ?
N1 C9 C5 119.7(4) . . ?
N1 C9 C8 121.6(4) . . ?
C8 C9 C5 118.8(4) . . ?
C5 C6 C7 120.8(4) . . ?
C1 C6 C5 120.5(4) . . ?
C1 C6 C7 118.7(4) . . ?
C8 C12 C11 115.6(4) . . ?
C8 C12 C13 120.1(4) . . ?
C11 C12 C13 124.3(4) . . ?
C6 C5 C9 119.1(4) . . ?
C6 C5 C4 118.9(4) . . ?
C4 C5 C9 122.0(4) . . ?
O1 C8 C9 121.2(4) . . ?
C12 C8 O1 116.9(4) . . ?
C12 C8 C9 121.9(4) . . ?
N1 C10 H10 117.7 . . ?
N1 C10 C11 124.5(4) . . ?
C11 C10 H10 117.7 . . ?
C12 C11 C10 119.5(4) . . ?
C12 C11 H11 120.3 . . ?
C10 C11 H11 120.3 . . ?
C5 C4 H4 119.9 . . ?
C3 C4 C5 120.1(4) . . ?
C3 C4 H4 119.9 . . ?
O1 C7 C6 117.4(4) . . ?
O2 C7 O1 116.9(4) . . ?
O2 C7 C6 125.8(4) . . ?
C6 C1 H1 120.1 . . ?
C2 C1 C6 119.9(4) . . ?
C2 C1 H1 120.1 . . ?
C1 C2 H2 120.0 . . ?
C1 C2 C3 119.9(4) . . ?
C3 C2 H2 120.0 . . ?
C12 C13 H13A 108.5 . . ?
C12 C13 H13B 108.5 . . ?
C12 C13 C14 115.2(4) . . ?
H13A C13 H13B 107.5 . . ?
C14 C13 H13A 108.5 . . ?
C14 C13 H13B 108.5 . . ?
C4 C3 C2 120.8(4) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 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
N1 C9 C5 C6 -179.9(4) . . . . ?
N1 C9 C5 C4 -0.1(6) . . . . ?
N1 C9 C8 O1 179.8(4) . . . . ?
N1 C9 C8 C12 -0.4(7) . . . . ?
N1 C10 C11 C12 0.0(8) . . . . ?
C9 N1 C10 C11 0.4(7) . . . . ?
C9 C5 C4 C3 -179.1(4) . . . . ?
C6 C5 C4 C3 0.7(7) . . . . ?
C6 C1 C2 C3 -0.5(7) . . . . ?
C5 C9 C8 O1 0.0(6) . . . . ?
C5 C9 C8 C12 179.8(4) . . . . ?
C5 C6 C7 O1 -1.3(6) . . . . ?
C5 C6 C7 O2 178.8(4) . . . . ?
C5 C6 C1 C2 0.6(7) . . . . ?
C5 C4 C3 C2 -0.6(7) . . . . ?
C8 O1 C7 O2 -179.0(4) . . . . ?
C8 O1 C7 C6 1.1(6) . . . . ?
C8 C9 C5 C6 -0.2(6) . . . . ?
C8 C9 C5 C4 179.6(4) . . . . ?
C8 C12 C11 C10 -0.5(7) . . . . ?
C8 C12 C13 C14 176.2(4) . . . . ?
C10 N1 C9 C5 179.6(4) . . . . ?
C10 N1 C9 C8 -0.2(6) . . . . ?
C11 C12 C8 O1 -179.4(4) . . . . ?
C11 C12 C8 C9 0.7(6) . . . . ?
C11 C12 C13 C14 -3.8(7) . . . . ?
C7 O1 C8 C9 -0.5(6) . . . . ?
C7 O1 C8 C12 179.6(4) . . . . ?
C7 C6 C5 C9 0.8(6) . . . . ?
C7 C6 C5 C4 -179.0(4) . . . . ?
C7 C6 C1 C2 179.0(4) . . . . ?
C1 C6 C5 C9 179.1(4) . . . . ?
C1 C6 C5 C4 -0.7(6) . . . . ?
C1 C6 C7 O1 -179.6(4) . . . . ?
C1 C6 C7 O2 0.5(7) . . . . ?
C1 C2 C3 C4 0.5(7) . . . . ?
C13 C12 C8 O1 0.5(6) . . . . ?
C13 C12 C8 C9 -179.3(4) . . . . ?
C13 C12 C11 C10 179.6(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
