# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2022

####################################################################### 
# 
# 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_11
_database_code_depnum_ccdc_archive 'CCDC 2117336'
loop_
_audit_author_name
_audit_author_address
Ln
;shihezi university
China
;
_audit_update_record             
;
2021-10-22 deposited with the CCDC.	2022-02-07 downloaded from the CCDC.
;
_audit_creation_date             2021-09-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H19 N3 O4'
_chemical_formula_sum            'C21 H19 N3 O4'
_chemical_formula_weight         377.39
_chemical_absolute_configuration ad
_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 0.0181 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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_H-M_alt        'P 21 21 2'
_space_group_name_Hall           'P 2 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.3671(3)
_cell_length_b                   14.9482(6)
_cell_length_c                   17.1529(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1888.96(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9895
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      68.13
_cell_measurement_theta_min      5.16
_shelx_estimated_absorpt_T_max   0.907
_shelx_estimated_absorpt_T_min   0.855
_exptl_absorpt_coefficient_mu    0.770
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6630
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1098 before and 0.0731 after correction. The Ratio of minimum to maximum transmission is 0.8804. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             792
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.13
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0597
_diffrn_reflns_av_unetI/netI     0.0200
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            48412
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.268
_diffrn_reflns_theta_min         2.576
_diffrn_ambient_temperature      173.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.727
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                3253
_reflns_number_total             3462
_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       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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         0.136
_refine_diff_density_min         -0.135
_refine_diff_density_rms         0.029
_refine_ls_abs_structure_details 
;
 Flack x determined using 1316 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.05(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3462
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0357
_refine_ls_R_factor_gt           0.0328
_refine_ls_restrained_S_all      1.039
_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)+(0.0402P)²+0.3160P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0804
_refine_ls_wR_factor_ref         0.0831
_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 Ternary CH refined with riding coordinates:
 C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C13(H13), C1(H1), C4(H4), C2(H2), C3(H3), C20(H20), C19(H19),
 C14(H14), C15(H15)
2.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C21(H21A,H21B,H21C)
;
_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
O3 O 0.3361(2) 0.78520(12) 0.19641(12) 0.0595(5) Uani 1 1 d . . . . .
O1 O 0.7750(3) 0.50479(10) 0.15983(9) 0.0555(4) Uani 1 1 d . . . . .
O4 O 0.6256(3) 0.74206(12) 0.43277(10) 0.0670(6) Uani 1 1 d . . . . .
N1 N 0.7417(2) 0.80355(11) 0.13192(9) 0.0383(4) Uani 1 1 d . . . . .
O2 O 0.7322(4) 0.57006(12) 0.27456(10) 0.0785(7) Uani 1 1 d . . . . .
N3 N 0.7054(3) 0.89542(14) 0.53242(11) 0.0557(5) Uani 1 1 d . . . . .
N2 N 0.7635(3) 0.96966(13) 0.42259(12) 0.0550(5) Uani 1 1 d . . . . .
C12 C 0.4447(3) 0.81476(14) 0.25549(13) 0.0400(5) Uani 1 1 d . . . . .
C5 C 0.8206(3) 0.75998(16) 0.06728(12) 0.0415(5) Uani 1 1 d . . . . .
C11 C 0.6196(3) 0.76559(14) 0.26630(12) 0.0377(5) Uani 1 1 d . . . . .
H11 H 0.589591 0.707808 0.292711 0.045 Uiso 1 1 calc R . . . .
C8 C 0.7070(3) 0.74225(13) 0.18950(11) 0.0362(4) Uani 1 1 d . . . . .
C7 C 0.7629(3) 0.65973(13) 0.16136(11) 0.0390(4) Uani 1 1 d . . . . .
C6 C 0.8322(3) 0.67084(15) 0.08512(12) 0.0436(5) Uani 1 1 d . . . . .
H6 H 0.878392 0.624958 0.052326 0.052 Uiso 1 1 calc R . . . .
C13 C 0.3654(3) 0.88366(15) 0.29251(16) 0.0512(6) Uani 1 1 d . . . . .
H13 H 0.413457 0.916362 0.335269 0.061 Uiso 1 1 calc R . . . .
C9 C 0.7533(3) 0.57601(14) 0.20546(12) 0.0454(5) Uani 1 1 d . . . . .
C18 C 0.7200(3) 0.89081(15) 0.45283(12) 0.0448(5) Uani 1 1 d . . . . .
C16 C 0.7467(3) 0.81703(15) 0.32108(12) 0.0441(5) Uani 1 1 d . . . . .
H16A H 0.871282 0.792951 0.315625 0.053 Uiso 1 1 calc R . . . .
H16B H 0.749360 0.880706 0.305242 0.053 Uiso 1 1 calc R . . . .
C17 C 0.6895(3) 0.81096(15) 0.40617(13) 0.0456(5) Uani 1 1 d . . . . .
C1 C 0.7131(3) 0.89540(15) 0.13159(13) 0.0460(5) Uani 1 1 d . . . . .
H1 H 0.657731 0.923829 0.175057 0.055 Uiso 1 1 calc R . . . .
C4 C 0.8717(3) 0.81352(18) 0.00226(13) 0.0532(6) Uani 1 1 d . . . . .
H4 H 0.924922 0.786144 -0.042183 0.064 Uiso 1 1 calc R . . . .
C2 C 0.7643(4) 0.94379(17) 0.06915(14) 0.0588(6) Uani 1 1 d . . . . .
H2 H 0.746104 1.006706 0.069141 0.071 Uiso 1 1 calc R . . . .
C3 C 0.8453(4) 0.90217(19) 0.00319(15) 0.0620(7) Uani 1 1 d . . . . .
H3 H 0.880864 0.937351 -0.040340 0.074 Uiso 1 1 calc R . . . .
C10 C 0.7695(4) 0.41949(15) 0.19887(17) 0.0633(7) Uani 1 1 d . . . . .
H10A H 0.783004 0.371426 0.160448 0.095 Uiso 1 1 calc GR . . . .
H10B H 0.653117 0.412917 0.225909 0.095 Uiso 1 1 calc GR . . . .
H10C H 0.868758 0.416109 0.236814 0.095 Uiso 1 1 calc GR . . . .
C20 C 0.7413(4) 0.9812(2) 0.55208(16) 0.0664(7) Uani 1 1 d . . . . .
H20 H 0.742162 1.005638 0.603195 0.080 Uiso 1 1 calc R . . . .
C19 C 0.7758(5) 1.02550(18) 0.48486(17) 0.0679(8) Uani 1 1 d . . . . .
H19 H 0.804718 1.087331 0.481658 0.082 Uiso 1 1 calc R . . . .
C14 C 0.1964(4) 0.89805(18) 0.2555(2) 0.0716(9) Uani 1 1 d . . . . .
H14 H 0.108559 0.941990 0.268820 0.086 Uiso 1 1 calc R . . . .
C15 C 0.1844(4) 0.8388(2) 0.1990(2) 0.0784(10) Uani 1 1 d . . . . .
H15 H 0.084080 0.833666 0.164435 0.094 Uiso 1 1 calc R . . . .
C21 C 0.6616(6) 0.8233(2) 0.58662(16) 0.0897(12) Uani 1 1 d . . . . .
H21A H 0.536668 0.803209 0.577594 0.135 Uiso 1 1 calc GR . . . .
H21B H 0.673387 0.845012 0.640278 0.135 Uiso 1 1 calc GR . . . .
H21C H 0.745157 0.773163 0.578360 0.135 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
O3 C12 1.365(3) . ?
O3 C15 1.375(3) . ?
O1 C9 1.331(3) . ?
O1 C10 1.441(3) . ?
O4 C17 1.221(3) . ?
N1 C5 1.411(3) . ?
N1 C8 1.371(3) . ?
N1 C1 1.389(3) . ?
O2 C9 1.199(3) . ?
N3 C18 1.371(3) . ?
N3 C20 1.352(4) . ?
N3 C21 1.460(4) . ?
N2 C18 1.327(3) . ?
N2 C19 1.359(3) . ?
C12 C11 1.495(3) . ?
C12 C13 1.344(3) . ?
C5 C6 1.370(3) . ?
C5 C4 1.423(3) . ?
C11 H11 1.0000 . ?
C11 C8 1.507(3) . ?
C11 C16 1.534(3) . ?
C8 C7 1.387(3) . ?
C7 C6 1.414(3) . ?
C7 C9 1.464(3) . ?
C6 H6 0.9500 . ?
C13 H13 0.9500 . ?
C13 C14 1.414(4) . ?
C18 C17 1.455(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.522(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.347(3) . ?
C4 H4 0.9500 . ?
C4 C3 1.339(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.422(4) . ?
C3 H3 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C20 H20 0.9500 . ?
C20 C19 1.354(4) . ?
C19 H19 0.9500 . ?
C14 H14 0.9500 . ?
C14 C15 1.317(4) . ?
C15 H15 0.9500 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 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
C12 O3 C15 105.3(2) . . ?
C9 O1 C10 115.54(18) . . ?
C8 N1 C5 109.53(17) . . ?
C8 N1 C1 129.41(18) . . ?
C1 N1 C5 121.04(18) . . ?
C18 N3 C21 127.9(2) . . ?
C20 N3 C18 106.3(2) . . ?
C20 N3 C21 125.8(2) . . ?
C18 N2 C19 104.8(2) . . ?
O3 C12 C11 116.00(18) . . ?
C13 C12 O3 110.1(2) . . ?
C13 C12 C11 133.9(2) . . ?
N1 C5 C4 117.7(2) . . ?
C6 C5 N1 107.41(18) . . ?
C6 C5 C4 134.9(2) . . ?
C12 C11 H11 106.9 . . ?
C12 C11 C8 111.94(17) . . ?
C12 C11 C16 110.85(17) . . ?
C8 C11 H11 106.9 . . ?
C8 C11 C16 112.99(17) . . ?
C16 C11 H11 106.9 . . ?
N1 C8 C11 123.68(18) . . ?
N1 C8 C7 106.74(17) . . ?
C7 C8 C11 129.56(18) . . ?
C8 C7 C6 108.96(18) . . ?
C8 C7 C9 124.47(18) . . ?
C6 C7 C9 126.57(19) . . ?
C5 C6 C7 107.36(19) . . ?
C5 C6 H6 126.3 . . ?
C7 C6 H6 126.3 . . ?
C12 C13 H13 126.6 . . ?
C12 C13 C14 106.7(2) . . ?
C14 C13 H13 126.6 . . ?
O1 C9 C7 111.97(17) . . ?
O2 C9 O1 122.5(2) . . ?
O2 C9 C7 125.49(19) . . ?
N3 C18 C17 125.2(2) . . ?
N2 C18 N3 111.3(2) . . ?
N2 C18 C17 123.44(19) . . ?
C11 C16 H16A 109.0 . . ?
C11 C16 H16B 109.0 . . ?
H16A C16 H16B 107.8 . . ?
C17 C16 C11 112.85(18) . . ?
C17 C16 H16A 109.0 . . ?
C17 C16 H16B 109.0 . . ?
O4 C17 C18 123.1(2) . . ?
O4 C17 C16 121.0(2) . . ?
C18 C17 C16 115.84(19) . . ?
N1 C1 H1 120.3 . . ?
C2 C1 N1 119.4(2) . . ?
C2 C1 H1 120.3 . . ?
C5 C4 H4 119.7 . . ?
C3 C4 C5 120.6(2) . . ?
C3 C4 H4 119.7 . . ?
C1 C2 H2 119.5 . . ?
C1 C2 C3 121.0(2) . . ?
C3 C2 H2 119.5 . . ?
C4 C3 C2 120.2(2) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
O1 C10 H10A 109.5 . . ?
O1 C10 H10B 109.5 . . ?
O1 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N3 C20 H20 126.6 . . ?
N3 C20 C19 106.8(2) . . ?
C19 C20 H20 126.6 . . ?
N2 C19 H19 124.6 . . ?
C20 C19 N2 110.9(2) . . ?
C20 C19 H19 124.6 . . ?
C13 C14 H14 126.6 . . ?
C15 C14 C13 106.7(2) . . ?
C15 C14 H14 126.6 . . ?
O3 C15 H15 124.4 . . ?
C14 C15 O3 111.1(3) . . ?
C14 C15 H15 124.4 . . ?
N3 C21 H21A 109.5 . . ?
N3 C21 H21B 109.5 . . ?
N3 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
