# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2082796'
loop_
_audit_author_name
_audit_author_address
'Han Zhangang'
;College of Chemistry and Material Science, Hebei Normal University, Shijiazhuang, Hebei
China
;
_audit_update_record             
;
2021-05-10 deposited with the CCDC.	2021-12-03 downloaded from the CCDC.
;
_audit_creation_date             2021-04-30
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H20 N2 O5'
_chemical_formula_sum            'C22 H20 N2 O5'
_chemical_formula_weight         392.40
_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   9.0099(6)
_cell_length_b                   16.3357(10)
_cell_length_c                   13.8677(9)
_cell_angle_alpha                90
_cell_angle_beta                 104.406(4)
_cell_angle_gamma                90
_cell_volume                     1976.9(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7782
_cell_measurement_temperature    296.26
_cell_measurement_theta_max      63.631
_cell_measurement_theta_min      4.261
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.780
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             824
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0414
_diffrn_reflns_av_unetI/netI     0.0322
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15755
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        63.746
_diffrn_reflns_theta_max         63.746
_diffrn_reflns_theta_min         4.261
_diffrn_ambient_temperature      296.26
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2603
_reflns_number_total             3244
_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 (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.281
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         3244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0622
_refine_ls_R_factor_gt           0.0489
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0626P)²+0.7598P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1225
_refine_ls_wR_factor_ref         0.1331
_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:
 C5(H5A,H5B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C7(H7), C11(H11), C12(H12), C13(H13), C15(H15),
 C17(H17), C19(H19), C20(H20), C22(H22)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.12867(15) 0.65594(8) 0.94808(10) 0.0450(4) Uani 1 1 d . . . . .
O2 O 0.6475(3) 0.48677(12) 1.26838(15) 0.0892(6) Uani 1 1 d . . . . .
O3 O 0.7385(2) 0.73088(11) 0.90750(19) 0.0954(7) Uani 1 1 d . . . . .
O4 O 0.6257(2) 0.36048(10) 1.20936(13) 0.0740(5) Uani 1 1 d . . . . .
O5 O 0.79464(19) 0.85620(9) 0.86814(13) 0.0629(5) Uani 1 1 d . . . . .
N1 N 0.28802(17) 0.56000(9) 1.03113(11) 0.0397(4) Uani 1 1 d . . . . .
N2 N 0.33245(19) 0.69842(10) 1.07776(12) 0.0459(4) Uani 1 1 d . . . . .
C1 C 0.2560(2) 0.64370(11) 1.02405(14) 0.0391(4) Uani 1 1 d . . . . .
C2 C -0.0448(3) 0.56559(14) 0.83027(17) 0.0544(6) Uani 1 1 d . . . . .
H2 H -0.107586 0.607798 0.798562 0.065 Uiso 1 1 calc R U . . .
C3 C 0.1737(3) 0.81261(14) 1.10434(17) 0.0567(6) Uani 1 1 d . . . . .
H3 H 0.126789 0.778613 1.141738 0.068 Uiso 1 1 calc R U . . .
C4 C 0.4088(2) 0.53032(13) 1.10443(15) 0.0438(5) Uani 1 1 d . . . . .
H4 H 0.466726 0.569655 1.145748 0.053 Uiso 1 1 calc R U . . .
C5 C 0.7508(3) 0.33469(18) 1.2912(2) 0.0796(8) Uani 1 1 d . . . . .
H5A H 0.724109 0.342913 1.354048 0.096 Uiso 1 1 calc R U . . .
H5B H 0.842133 0.366357 1.291833 0.096 Uiso 1 1 calc R U . . .
C6 C 0.0800(2) 0.57993(12) 0.90768(15) 0.0432(5) Uani 1 1 d . . . . .
C7 C 0.0217(3) 0.42312(14) 0.85095(18) 0.0597(6) Uani 1 1 d . . . . .
H7 H -0.000157 0.369284 0.830492 0.072 Uiso 1 1 calc R U . . .
C8 C 0.1759(2) 0.51938(11) 0.95710(14) 0.0404(4) Uani 1 1 d . . . . .
C9 C 0.9274(3) 0.82591(16) 0.83953(18) 0.0616(6) Uani 1 1 d . . . . .
H9A H 0.895462 0.794941 0.779072 0.092 Uiso 1 1 calc R U . . .
H9B H 0.985664 0.791408 0.891325 0.092 Uiso 1 1 calc R U . . .
H9C H 0.989574 0.871150 0.829112 0.092 Uiso 1 1 calc R U . . .
C10 C 0.2855(2) 0.78117(12) 1.06179(15) 0.0434(5) Uani 1 1 d . . . . .
C11 C 0.5811(3) 0.84189(13) 0.93063(17) 0.0523(5) Uani 1 1 d . . . . .
H11 H 0.567638 0.898062 0.921641 0.063 Uiso 1 1 calc R U . . .
C12 C 0.4529(3) 0.45508(13) 1.12382(16) 0.0512(5) Uani 1 1 d . . . . .
H12 H 0.401421 0.412511 1.084923 0.061 Uiso 1 1 calc R U . . .
C13 C -0.0724(3) 0.48477(15) 0.80188(18) 0.0592(6) Uani 1 1 d . . . . .
H13 H -0.155133 0.471751 0.749146 0.071 Uiso 1 1 calc R U . . .
C14 C 0.7090(2) 0.80243(12) 0.90121(16) 0.0480(5) Uani 1 1 d . . . . .
C15 C 0.3124(3) 0.91481(13) 0.99551(19) 0.0561(6) Uani 1 1 d . . . . .
H15 H 0.358041 0.949708 0.958387 0.067 Uiso 1 1 calc R U . . .
C16 C 0.5853(3) 0.43779(14) 1.20813(17) 0.0534(5) Uani 1 1 d . . . . .
C17 C 0.1313(3) 0.89374(15) 1.09177(19) 0.0636(6) Uani 1 1 d . . . . .
H17 H 0.056185 0.914167 1.120680 0.076 Uiso 1 1 calc R U . . .
C18 C 0.3603(2) 0.83289(12) 1.00818(15) 0.0443(5) Uani 1 1 d . . . . .
C19 C 0.1997(3) 0.94449(14) 1.0366(2) 0.0624(6) Uani 1 1 d . . . . .
H19 H 0.169677 0.998968 1.027236 0.075 Uiso 1 1 calc R U . . .
C20 C 0.4852(2) 0.80085(12) 0.96912(16) 0.0492(5) Uani 1 1 d . . . . .
H20 H 0.498040 0.744333 0.971993 0.059 Uiso 1 1 calc R U . . .
C21 C 0.7785(4) 0.24819(18) 1.2770(3) 0.0942(10) Uani 1 1 d . . . . .
H21A H 0.803662 0.240686 1.214211 0.141 Uiso 1 1 calc R U . . .
H21B H 0.688071 0.217347 1.277578 0.141 Uiso 1 1 calc R U . . .
H21C H 0.862123 0.229523 1.329740 0.141 Uiso 1 1 calc R U . . .
C22 C 0.1482(2) 0.43868(13) 0.93004(16) 0.0504(5) Uani 1 1 d . . . . .
H22 H 0.210622 0.396729 0.962777 0.061 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.366(2) . ?
O1 C6 1.388(2) . ?
O2 C16 1.191(3) . ?
O3 C14 1.197(3) . ?
O4 C5 1.449(3) . ?
O4 C16 1.313(3) . ?
O5 C9 1.438(3) . ?
O5 C14 1.324(3) . ?
N1 C1 1.396(2) . ?
N1 C4 1.379(3) . ?
N1 C8 1.414(2) . ?
N2 C1 1.254(2) . ?
N2 C10 1.417(2) . ?
C2 H2 0.9300 . ?
C2 C6 1.368(3) . ?
C2 C13 1.382(3) . ?
C3 H3 0.9300 . ?
C3 C10 1.387(3) . ?
C3 C17 1.378(3) . ?
C4 H4 0.9300 . ?
C4 C12 1.299(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C21 1.457(4) . ?
C6 C8 1.378(3) . ?
C7 H7 0.9300 . ?
C7 C13 1.381(3) . ?
C7 C22 1.395(3) . ?
C8 C22 1.376(3) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C18 1.404(3) . ?
C11 H11 0.9300 . ?
C11 C14 1.464(3) . ?
C11 C20 1.308(3) . ?
C12 H12 0.9300 . ?
C12 C16 1.475(3) . ?
C13 H13 0.9300 . ?
C15 H15 0.9300 . ?
C15 C18 1.404(3) . ?
C15 C19 1.370(3) . ?
C17 H17 0.9300 . ?
C17 C19 1.374(4) . ?
C18 C20 1.462(3) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22 0.9300 . ?

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
C1 O1 C6 107.50(14) . . ?
C16 O4 C5 116.7(2) . . ?
C14 O5 C9 117.62(17) . . ?
C1 N1 C8 108.11(15) . . ?
C4 N1 C1 120.51(17) . . ?
C4 N1 C8 131.33(17) . . ?
C1 N2 C10 119.24(17) . . ?
O1 C1 N1 108.48(16) . . ?
N2 C1 O1 125.85(17) . . ?
N2 C1 N1 125.67(18) . . ?
C6 C2 H2 121.9 . . ?
C6 C2 C13 116.2(2) . . ?
C13 C2 H2 121.9 . . ?
C10 C3 H3 119.7 . . ?
C17 C3 H3 119.7 . . ?
C17 C3 C10 120.7(2) . . ?
N1 C4 H4 115.5 . . ?
C12 C4 N1 129.0(2) . . ?
C12 C4 H4 115.5 . . ?
O4 C5 H5A 110.2 . . ?
O4 C5 H5B 110.2 . . ?
O4 C5 C21 107.6(2) . . ?
H5A C5 H5B 108.5 . . ?
C21 C5 H5A 110.2 . . ?
C21 C5 H5B 110.2 . . ?
C2 C6 O1 125.84(18) . . ?
C2 C6 C8 123.95(19) . . ?
C8 C6 O1 110.21(17) . . ?
C13 C7 H7 118.8 . . ?
C13 C7 C22 122.4(2) . . ?
C22 C7 H7 118.8 . . ?
C6 C8 N1 105.69(16) . . ?
C22 C8 N1 134.08(18) . . ?
C22 C8 C6 120.22(19) . . ?
O5 C9 H9A 109.5 . . ?
O5 C9 H9B 109.5 . . ?
O5 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C3 C10 N2 120.48(19) . . ?
C3 C10 C18 119.86(19) . . ?
C18 C10 N2 119.51(18) . . ?
C14 C11 H11 118.9 . . ?
C20 C11 H11 118.9 . . ?
C20 C11 C14 122.26(19) . . ?
C4 C12 H12 120.3 . . ?
C4 C12 C16 119.4(2) . . ?
C16 C12 H12 120.3 . . ?
C2 C13 H13 119.6 . . ?
C7 C13 C2 120.8(2) . . ?
C7 C13 H13 119.6 . . ?
O3 C14 O5 122.3(2) . . ?
O3 C14 C11 125.8(2) . . ?
O5 C14 C11 111.80(17) . . ?
C18 C15 H15 119.3 . . ?
C19 C15 H15 119.3 . . ?
C19 C15 C18 121.5(2) . . ?
O2 C16 O4 123.8(2) . . ?
O2 C16 C12 125.0(2) . . ?
O4 C16 C12 111.2(2) . . ?
C3 C17 H17 119.9 . . ?
C19 C17 C3 120.1(2) . . ?
C19 C17 H17 119.9 . . ?
C10 C18 C20 119.75(18) . . ?
C15 C18 C10 117.81(19) . . ?
C15 C18 C20 122.44(19) . . ?
C15 C19 C17 120.0(2) . . ?
C15 C19 H19 120.0 . . ?
C17 C19 H19 120.0 . . ?
C11 C20 C18 127.98(19) . . ?
C11 C20 H20 116.0 . . ?
C18 C20 H20 116.0 . . ?
C5 C21 H21A 109.5 . . ?
C5 C21 H21B 109.5 . . ?
C5 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C7 C22 H22 121.8 . . ?
C8 C22 C7 116.5(2) . . ?
C8 C22 H22 121.8 . . ?

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 C6 C8 N1 0.1(2) . . . . ?
O1 C6 C8 C22 179.30(18) . . . . ?
N1 C4 C12 C16 -178.94(19) . . . . ?
N1 C8 C22 C7 179.7(2) . . . . ?
N2 C10 C18 C15 -178.85(19) . . . . ?
N2 C10 C18 C20 0.3(3) . . . . ?
C1 O1 C6 C2 179.5(2) . . . . ?
C1 O1 C6 C8 -0.3(2) . . . . ?
C1 N1 C4 C12 178.1(2) . . . . ?
C1 N1 C8 C6 0.1(2) . . . . ?
C1 N1 C8 C22 -178.9(2) . . . . ?
C1 N2 C10 C3 83.8(3) . . . . ?
C1 N2 C10 C18 -100.5(2) . . . . ?
C2 C6 C8 N1 -179.71(19) . . . . ?
C2 C6 C8 C22 -0.5(3) . . . . ?
C3 C10 C18 C15 -3.2(3) . . . . ?
C3 C10 C18 C20 175.90(19) . . . . ?
C3 C17 C19 C15 -1.2(4) . . . . ?
C4 N1 C1 O1 -177.86(15) . . . . ?
C4 N1 C1 N2 2.9(3) . . . . ?
C4 N1 C8 C6 177.34(18) . . . . ?
C4 N1 C8 C22 -1.7(4) . . . . ?
C4 C12 C16 O2 8.7(4) . . . . ?
C4 C12 C16 O4 -172.1(2) . . . . ?
C5 O4 C16 O2 1.7(4) . . . . ?
C5 O4 C16 C12 -177.5(2) . . . . ?
C6 O1 C1 N1 0.32(19) . . . . ?
C6 O1 C1 N2 179.60(19) . . . . ?
C6 C2 C13 C7 0.7(3) . . . . ?
C6 C8 C22 C7 0.7(3) . . . . ?
C8 N1 C1 O1 -0.3(2) . . . . ?
C8 N1 C1 N2 -179.54(18) . . . . ?
C8 N1 C4 C12 1.1(3) . . . . ?
C9 O5 C14 O3 -0.2(3) . . . . ?
C9 O5 C14 C11 178.12(19) . . . . ?
C10 N2 C1 O1 1.0(3) . . . . ?
C10 N2 C1 N1 -179.88(18) . . . . ?
C10 C3 C17 C19 0.0(4) . . . . ?
C10 C18 C20 C11 -169.3(2) . . . . ?
C13 C2 C6 O1 179.98(19) . . . . ?
C13 C2 C6 C8 -0.2(3) . . . . ?
C13 C7 C22 C8 -0.3(3) . . . . ?
C14 C11 C20 C18 175.2(2) . . . . ?
C15 C18 C20 C11 9.8(4) . . . . ?
C16 O4 C5 C21 -178.8(2) . . . . ?
C17 C3 C10 N2 177.8(2) . . . . ?
C17 C3 C10 C18 2.2(3) . . . . ?
C18 C15 C19 C17 0.1(4) . . . . ?
C19 C15 C18 C10 2.1(3) . . . . ?
C19 C15 C18 C20 -177.0(2) . . . . ?
C20 C11 C14 O3 0.9(4) . . . . ?
C20 C11 C14 O5 -177.3(2) . . . . ?
C22 C7 C13 C2 -0.5(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_zhaoyl20210903_2_0m
_database_code_depnum_ccdc_archive 'CCDC 2108953'
loop_
_audit_author_name
_audit_author_address
'Han Zhangang'
;C
China
;
_audit_update_record             
;
2021-09-10 deposited with the CCDC.	2021-12-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H16 Br2 N2 O4'
_chemical_formula_weight         484.15

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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   8.3908(4)
_cell_length_b                   9.1933(4)
_cell_length_c                   13.3036(5)
_cell_angle_alpha                98.496(2)
_cell_angle_beta                 101.364(2)
_cell_angle_gamma                106.129(2)
_cell_volume                     943.91(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    5265
_cell_measurement_theta_min      3.47
_cell_measurement_theta_max      63.80

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.703
_exptl_crystal_F_000             480
_exptl_transmission_factor_min   0.502
_exptl_transmission_factor_max   0.600
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_exptl_absorpt_coefficient_mu    5.677
_shelx_estimated_absorpt_T_min   0.502
_shelx_estimated_absorpt_T_max   0.600
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7929
_diffrn_reflns_av_unetI/netI     0.0450
_diffrn_reflns_av_R_equivalents  0.0398
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.470
_diffrn_reflns_theta_max         63.800
_diffrn_reflns_theta_full        63.800
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             3091
_reflns_number_gt                2495
_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker 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)+(0.0418P)²+2.2834P] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0095(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3091
_refine_ls_number_parameters     241
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0625
_refine_ls_R_factor_gt           0.0500
_refine_ls_wR_factor_ref         0.1305
_refine_ls_wR_factor_gt          0.1206
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.011
_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
Br1 Br -0.48227(9) -0.28585(7) 0.17864(5) 0.0770(3) Uani 1 1 d . . . . .
Br2 Br 0.52132(10) 0.70212(8) 0.90631(5) 0.0846(3) Uani 1 1 d . . . . .
C1 C 0.3833(6) 0.6252(5) 0.5842(4) 0.0412(10) Uani 1 1 d . . . . .
C2 C 0.3815(6) 0.6124(5) 0.6860(4) 0.0491(11) Uani 1 1 d . . . . .
H2 H 0.2916 0.5413 0.7014 0.059 Uiso 1 1 calc R U . . .
C3 C 0.5205(7) 0.7112(6) 0.7640(4) 0.0568(13) Uani 1 1 d . . . . .
C6 C 0.5195(6) 0.7326(5) 0.5639(4) 0.0490(12) Uani 1 1 d . . . . .
C4 C 0.6540(7) 0.8193(6) 0.7447(5) 0.0675(16) Uani 1 1 d . . . . .
H4 H 0.7429 0.8847 0.8002 0.081 Uiso 1 1 calc R U . . .
C5 C 0.6557(7) 0.8308(6) 0.6418(5) 0.0649(16) Uani 1 1 d . . . . .
H5 H 0.7456 0.9021 0.6265 0.078 Uiso 1 1 calc R U . . .
C7 C 0.3301(6) 0.6239(5) 0.4052(4) 0.0457(11) Uani 1 1 d . . . . .
H7 H 0.3334 0.5456 0.3477 0.055 Uiso 1 1 calc R U . . .
C8 C 0.2282(7) 0.7250(6) 0.3619(4) 0.0552(13) Uani 1 1 d . . . . .
H8A H 0.1578 0.7441 0.4089 0.066 Uiso 1 1 calc R U . . .
H8B H 0.3083 0.8243 0.3623 0.066 Uiso 1 1 calc R U . . .
C9 C 0.1164(7) 0.6597(6) 0.2547(5) 0.0599(14) Uani 1 1 d . . . . .
C10 C 0.1416(5) 0.4063(5) 0.4713(3) 0.0384(10) Uani 1 1 d . . . . .
C11 C -0.0714(5) 0.1964(5) 0.3300(3) 0.0380(10) Uani 1 1 d . . . . .
C12 C -0.1033(6) 0.0826(5) 0.3889(4) 0.0477(11) Uani 1 1 d . . . . .
H12 H -0.0429 0.1028 0.4587 0.057 Uiso 1 1 calc R U . . .
C13 C -0.2255(7) -0.0610(5) 0.3428(4) 0.0528(12) Uani 1 1 d . . . . .
H13 H -0.2458 -0.1379 0.3813 0.063 Uiso 1 1 calc R U . . .
C14 C -0.3159(6) -0.0889(5) 0.2407(4) 0.0468(11) Uani 1 1 d . . . . .
C15 C -0.2837(7) 0.0216(6) 0.1817(4) 0.0544(12) Uani 1 1 d . . . . .
H15 H -0.3436 0.0009 0.1118 0.065 Uiso 1 1 calc R U . . .
C16 C -0.1616(7) 0.1634(5) 0.2275(4) 0.0486(11) Uani 1 1 d . . . . .
H16 H -0.1401 0.2385 0.1877 0.058 Uiso 1 1 calc R U . . .
C17 C -0.0413(11) 0.7178(11) 0.1062(7) 0.130(4) Uani 1 1 d D . . . .
H17A H -0.0794 0.6055 0.0867 0.156 Uiso 1 1 calc R U . . .
H17B H -0.1410 0.7512 0.1073 0.156 Uiso 1 1 calc R U . . .
C18 C 0.0421(15) 0.781(2) 0.0309(7) 0.217(8) Uani 1 1 d D . . . .
H18A H 0.1023 0.8895 0.0582 0.325 Uiso 1 1 calc R U . . .
H18B H -0.0420 0.7678 -0.0330 0.325 Uiso 1 1 calc R U . . .
H18C H 0.1220 0.7282 0.0171 0.325 Uiso 1 1 calc R U . . .
N1 N 0.2669(5) 0.5484(4) 0.4869(3) 0.0416(9) Uani 1 1 d . . . . .
N2 N 0.0533(5) 0.3438(4) 0.3705(3) 0.0433(9) Uani 1 1 d . . . . .
O1 O 0.1156(4) 0.3488(4) 0.5456(2) 0.0504(8) Uani 1 1 d . . . . .
O2 O 0.4995(4) 0.7220(4) 0.4575(3) 0.0603(9) Uani 1 1 d . . . . .
O3 O 0.0674(6) 0.5246(5) 0.2115(3) 0.0873(14) Uani 1 1 d . . . . .
O4 O 0.0769(6) 0.7697(5) 0.2101(4) 0.0848(13) Uani 1 1 d . . . . .
H1A H 0.067(6) 0.394(5) 0.330(4) 0.034(12) Uiso 1 1 d . . . . .


_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
Br1 C14 1.899(4) . ?
Br2 C3 1.905(6) . ?
C1 C2 1.379(7) . ?
C1 C6 1.388(6) . ?
C1 N1 1.406(6) . ?
C2 C3 1.385(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.371(8) . ?
C6 C5 1.371(7) . ?
C6 O2 1.378(6) . ?
C4 C5 1.392(9) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C7 O2 1.425(6) . ?
C7 N1 1.479(5) . ?
C7 C8 1.527(7) . ?
C7 H7 0.9800 . ?
C8 C9 1.478(8) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 O3 1.206(7) . ?
C9 O4 1.330(6) . ?
C10 O1 1.216(5) . ?
C10 N2 1.350(6) . ?
C10 N1 1.388(5) . ?
C11 C16 1.368(6) . ?
C11 C12 1.396(6) . ?
C11 N2 1.412(5) . ?
C12 C13 1.390(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.368(7) . ?
C13 H13 0.9300 . ?
C14 C15 1.373(7) . ?
C15 C16 1.377(7) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C18 1.434(8) . ?
C17 O4 1.457(9) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
N2 H1A 0.77(5) . ?

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
C2 C1 C6 120.3(4) . . ?
C2 C1 N1 132.7(4) . . ?
C6 C1 N1 107.0(4) . . ?
C1 C2 C3 116.5(5) . . ?
C1 C2 H2 121.8 . . ?
C3 C2 H2 121.8 . . ?
C4 C3 C2 123.6(5) . . ?
C4 C3 Br2 118.2(4) . . ?
C2 C3 Br2 118.2(4) . . ?
C5 C6 O2 126.3(5) . . ?
C5 C6 C1 122.8(5) . . ?
O2 C6 C1 110.9(4) . . ?
C3 C4 C5 119.7(5) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C6 C5 C4 117.2(5) . . ?
C6 C5 H5 121.4 . . ?
C4 C5 H5 121.4 . . ?
O2 C7 N1 104.3(4) . . ?
O2 C7 C8 107.9(4) . . ?
N1 C7 C8 114.3(4) . . ?
O2 C7 H7 110.0 . . ?
N1 C7 H7 110.0 . . ?
C8 C7 H7 110.0 . . ?
C9 C8 C7 115.3(4) . . ?
C9 C8 H8A 108.5 . . ?
C7 C8 H8A 108.5 . . ?
C9 C8 H8B 108.5 . . ?
C7 C8 H8B 108.5 . . ?
H8A C8 H8B 107.5 . . ?
O3 C9 O4 123.6(6) . . ?
O3 C9 C8 125.1(5) . . ?
O4 C9 C8 111.4(5) . . ?
O1 C10 N2 124.8(4) . . ?
O1 C10 N1 120.3(4) . . ?
N2 C10 N1 114.8(4) . . ?
C16 C11 C12 118.9(4) . . ?
C16 C11 N2 117.9(4) . . ?
C12 C11 N2 123.1(4) . . ?
C13 C12 C11 119.8(4) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C14 C13 C12 119.8(4) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C13 C14 C15 120.8(4) . . ?
C13 C14 Br1 119.3(3) . . ?
C15 C14 Br1 119.8(4) . . ?
C14 C15 C16 119.2(4) . . ?
C14 C15 H15 120.4 . . ?
C16 C15 H15 120.4 . . ?
C11 C16 C15 121.5(4) . . ?
C11 C16 H16 119.3 . . ?
C15 C16 H16 119.3 . . ?
C18 C17 O4 109.8(7) . . ?
C18 C17 H17A 109.7 . . ?
O4 C17 H17A 109.7 . . ?
C18 C17 H17B 109.7 . . ?
O4 C17 H17B 109.7 . . ?
H17A C17 H17B 108.2 . . ?
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 . . ?
C10 N1 C1 123.5(4) . . ?
C10 N1 C7 127.0(4) . . ?
C1 N1 C7 107.8(3) . . ?
C10 N2 C11 127.5(4) . . ?
C10 N2 H1A 118(3) . . ?
C11 N2 H1A 114(3) . . ?
C6 O2 C7 108.2(3) . . ?
C9 O4 C17 116.3(5) . . ?

_refine_diff_density_max         0.969
_refine_diff_density_min         -0.718
_refine_diff_density_rms         0.082

