# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2021

####################################################################### 
# 
# 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_200921_s3_yxh
_database_code_depnum_ccdc_archive 'CCDC 2043200'
loop_
_audit_author_name
_audit_author_address
'Xiaoyun Ran'
;Xihua University
China
;
_audit_update_record             
;
2020-11-09 deposited with the CCDC.	2021-04-26 downloaded from the CCDC.
;
_audit_creation_date             2020-09-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C20 H15 N2 O3'
_chemical_formula_sum            'C20 H15 N2 O3'
_chemical_formula_weight         331.34
_chemical_absolute_configuration unk
_chemical_melting_point          ?
_chemical_oxdiff_formula         c12h12n2o3
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      tetragonal
_space_group_IT_number           76
_space_group_name_H-M_alt        'P 41'
_space_group_name_Hall           'P 4w'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x, z+1/4'
'-x, -y, z+1/2'
'y, -x, z+3/4'

_cell_length_a                   10.6876(20)
_cell_length_b                   10.6876(20)
_cell_length_c                   14.146(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1615.8(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    843
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.7440
_cell_measurement_theta_min      3.9250
_shelx_estimated_absorpt_T_max   0.995
_shelx_estimated_absorpt_T_min   0.968
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.36167
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             692
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_av_unetI/netI     0.0652
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            3536
_diffrn_reflns_point_group_measured_fraction_full 0.738
_diffrn_reflns_point_group_measured_fraction_max 0.723
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         3.056
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0874
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -13.00   14.00   1.0000   31.0000
omega____ theta____ kappa____ phi______ frames
    -      -15.6336  -99.0000  120.0000 27

#__ type_ start__ end____ width___ exp.time_
  2 omega  -53.00   24.00   1.0000   31.0000
omega____ theta____ kappa____ phi______ frames
    -       17.6648  -19.0000  -30.0000 77
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0557301000
_diffrn_orient_matrix_UB_12      -0.0118601000
_diffrn_orient_matrix_UB_13      0.0258760000
_diffrn_orient_matrix_UB_21      0.0061935000
_diffrn_orient_matrix_UB_22      -0.0584885000
_diffrn_orient_matrix_UB_23      -0.0231472000
_diffrn_orient_matrix_UB_31      0.0354465000
_diffrn_orient_matrix_UB_32      0.0287180000
_diffrn_orient_matrix_UB_33      -0.0366095000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.391
_reflns_Friedel_fraction_full    0.454
_reflns_Friedel_fraction_max     0.425
_reflns_number_gt                1553
_reflns_number_total             2393
_reflns_odcompleteness_completeness 99.54
_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, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 
;
 Flack x determined using 378 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.2(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.909
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         2393
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0730
_refine_ls_R_factor_gt           0.0417
_refine_ls_restrained_S_all      0.909
_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)+(0.0296P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0748
_refine_ls_wR_factor_ref         0.0849
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6), C7(H7)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14), C16(H16),
 C17(H17), C18(H18), C19(H19), C20(H20)
2.c Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_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 0.9471(2) 0.4428(2) -0.04280(17) 0.0433(7) Uani 1 1 d . . . . .
O2 O 0.7594(3) 0.1514(3) 0.2860(2) 0.0745(10) Uani 1 1 d . . . . .
O3 O 0.6862(3) 0.1405(3) 0.1384(2) 0.0611(8) Uani 1 1 d . . . . .
H3 H 0.6544 0.0752 0.1571 0.092 Uiso 1 1 calc GR . . . .
N1 N 0.9978(3) 0.4713(3) 0.1118(2) 0.0355(7) Uani 1 1 d . . . . .
N2 N 1.0861(3) 0.5058(3) 0.2531(2) 0.0540(9) Uani 1 1 d . . . . .
C1 C 0.9289(3) 0.4117(3) 0.0420(3) 0.0359(9) Uani 1 1 d . . . . .
C2 C 0.8468(3) 0.3196(3) 0.0766(3) 0.0396(10) Uani 1 1 d . . . . .
H2 H 0.7936 0.2787 0.0348 0.048 Uiso 1 1 calc R . . . .
C3 C 0.8434(3) 0.2886(3) 0.1708(3) 0.0397(9) Uani 1 1 d . . . . .
C4 C 0.9198(3) 0.3466(4) 0.2375(3) 0.0455(10) Uani 1 1 d . . . . .
H4 H 0.9171 0.3241 0.3009 0.055 Uiso 1 1 calc R . . . .
C5 C 0.9994(3) 0.4383(3) 0.2058(3) 0.0413(10) Uani 1 1 d . . . . .
C6 C 1.1570(3) 0.5876(4) 0.1885(3) 0.0421(10) Uani 1 1 d . . . . .
H6 H 1.1496 0.6743 0.2104 0.050 Uiso 1 1 calc R . . . .
C7 C 1.0858(3) 0.5741(3) 0.0922(3) 0.0391(9) Uani 1 1 d . . . . .
H7 H 1.1444 0.5493 0.0423 0.047 Uiso 1 1 calc R . . . .
C8 C 0.7586(4) 0.1874(4) 0.2055(3) 0.0458(10) Uani 1 1 d . . . . .
C9 C 1.2931(3) 0.5545(3) 0.1811(3) 0.0397(9) Uani 1 1 d . . . . .
C10 C 1.3316(4) 0.4328(4) 0.1717(3) 0.0556(12) Uani 1 1 d . . . . .
H10 H 1.2728 0.3687 0.1723 0.067 Uiso 1 1 calc R . . . .
C11 C 1.4573(5) 0.4041(5) 0.1613(3) 0.0724(15) Uani 1 1 d . . . . .
H11 H 1.4834 0.3215 0.1555 0.087 Uiso 1 1 calc R . . . .
C12 C 1.5436(4) 0.5015(6) 0.1596(3) 0.0752(15) Uani 1 1 d . . . . .
H12 H 1.6282 0.4838 0.1521 0.090 Uiso 1 1 calc R . . . .
C13 C 1.5061(4) 0.6209(5) 0.1687(3) 0.0633(13) Uani 1 1 d . . . . .
H13 H 1.5648 0.6850 0.1669 0.076 Uiso 1 1 calc R . . . .
C14 C 1.3820(4) 0.6490(4) 0.1807(3) 0.0471(10) Uani 1 1 d . . . . .
H14 H 1.3573 0.7318 0.1886 0.056 Uiso 1 1 calc R . . . .
C15 C 1.0206(3) 0.6938(4) 0.0650(3) 0.0378(9) Uani 1 1 d . . . . .
C16 C 0.9102(4) 0.7296(4) 0.1077(3) 0.0474(11) Uani 1 1 d . . . . .
H16 H 0.8697 0.6748 0.1486 0.057 Uiso 1 1 calc R . . . .
C17 C 0.8593(4) 0.8462(4) 0.0902(3) 0.0540(12) Uani 1 1 d . . . . .
H17 H 0.7851 0.8702 0.1195 0.065 Uiso 1 1 calc R . . . .
C18 C 0.9188(5) 0.9261(4) 0.0296(3) 0.0624(13) Uani 1 1 d . . . . .
H18 H 0.8852 1.0049 0.0181 0.075 Uiso 1 1 calc R . . . .
C19 C 1.0261(5) 0.8914(4) -0.0137(4) 0.0715(14) Uani 1 1 d . . . . .
H19 H 1.0654 0.9461 -0.0553 0.086 Uiso 1 1 calc R . . . .
C20 C 1.0773(4) 0.7761(4) 0.0036(3) 0.0573(11) Uani 1 1 d . . . . .
H20 H 1.1511 0.7531 -0.0265 0.069 Uiso 1 1 calc R . . . .


_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 1.260(4) . ?
O2 C8 1.201(5) . ?
O3 H3 0.8200 . ?
O3 C8 1.324(5) . ?
N1 C1 1.386(4) . ?
N1 C5 1.375(4) . ?
N1 C7 1.473(4) . ?
N2 C5 1.352(4) . ?
N2 C6 1.475(5) . ?
C1 C2 1.407(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.373(5) . ?
C3 C4 1.393(5) . ?
C3 C8 1.494(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.373(5) . ?
C6 H6 0.9800 . ?
C6 C7 1.566(5) . ?
C6 C9 1.501(5) . ?
C7 H7 0.9800 . ?
C7 C15 1.506(5) . ?
C9 C10 1.371(5) . ?
C9 C14 1.387(5) . ?
C10 H10 0.9300 . ?
C10 C11 1.385(6) . ?
C11 H11 0.9300 . ?
C11 C12 1.391(6) . ?
C12 H12 0.9300 . ?
C12 C13 1.343(6) . ?
C13 H13 0.9300 . ?
C13 C14 1.370(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.379(5) . ?
C15 C20 1.377(5) . ?
C16 H16 0.9300 . ?
C16 C17 1.383(5) . ?
C17 H17 0.9300 . ?
C17 C18 1.366(6) . ?
C18 H18 0.9300 . ?
C18 C19 1.352(6) . ?
C19 H19 0.9300 . ?
C19 C20 1.370(5) . ?
C20 H20 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
C8 O3 H3 109.5 . . ?
C1 N1 C7 123.2(3) . . ?
C5 N1 C1 125.3(3) . . ?
C5 N1 C7 111.4(3) . . ?
C5 N2 C6 111.1(3) . . ?
O1 C1 N1 118.4(3) . . ?
O1 C1 C2 127.7(3) . . ?
N1 C1 C2 113.9(3) . . ?
C1 C2 H2 119.2 . . ?
C3 C2 C1 121.5(3) . . ?
C3 C2 H2 119.2 . . ?
C2 C3 C4 122.3(3) . . ?
C2 C3 C8 120.6(4) . . ?
C4 C3 C8 117.1(4) . . ?
C3 C4 H4 121.3 . . ?
C5 C4 C3 117.4(4) . . ?
C5 C4 H4 121.3 . . ?
N2 C5 N1 110.6(3) . . ?
N2 C5 C4 130.1(4) . . ?
C4 C5 N1 119.4(3) . . ?
N2 C6 H6 108.8 . . ?
N2 C6 C7 103.6(3) . . ?
N2 C6 C9 113.6(3) . . ?
C7 C6 H6 108.8 . . ?
C9 C6 H6 108.8 . . ?
C9 C6 C7 112.9(3) . . ?
N1 C7 C6 102.4(3) . . ?
N1 C7 H7 110.0 . . ?
N1 C7 C15 112.7(3) . . ?
C6 C7 H7 110.0 . . ?
C15 C7 C6 111.6(3) . . ?
C15 C7 H7 110.0 . . ?
O2 C8 O3 124.2(4) . . ?
O2 C8 C3 122.6(4) . . ?
O3 C8 C3 113.1(4) . . ?
C10 C9 C6 121.4(4) . . ?
C10 C9 C14 119.0(4) . . ?
C14 C9 C6 119.5(3) . . ?
C9 C10 H10 119.6 . . ?
C9 C10 C11 120.8(5) . . ?
C11 C10 H10 119.6 . . ?
C10 C11 H11 120.7 . . ?
C10 C11 C12 118.6(4) . . ?
C12 C11 H11 120.7 . . ?
C11 C12 H12 119.6 . . ?
C13 C12 C11 120.7(4) . . ?
C13 C12 H12 119.6 . . ?
C12 C13 H13 119.7 . . ?
C12 C13 C14 120.6(5) . . ?
C14 C13 H13 119.7 . . ?
C9 C14 H14 119.9 . . ?
C13 C14 C9 120.2(4) . . ?
C13 C14 H14 119.9 . . ?
C16 C15 C7 121.3(4) . . ?
C20 C15 C7 120.0(4) . . ?
C20 C15 C16 118.4(4) . . ?
C15 C16 H16 119.7 . . ?
C15 C16 C17 120.6(4) . . ?
C17 C16 H16 119.7 . . ?
C16 C17 H17 120.3 . . ?
C18 C17 C16 119.4(4) . . ?
C18 C17 H17 120.3 . . ?
C17 C18 H18 119.7 . . ?
C19 C18 C17 120.5(4) . . ?
C19 C18 H18 119.7 . . ?
C18 C19 H19 119.9 . . ?
C18 C19 C20 120.3(5) . . ?
C20 C19 H19 119.9 . . ?
C15 C20 H20 119.6 . . ?
C19 C20 C15 120.8(4) . . ?
C19 C20 H20 119.6 . . ?

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 174.9(4) . . . . ?
N1 C1 C2 C3 -3.8(5) . . . . ?
N1 C7 C15 C16 37.8(5) . . . . ?
N1 C7 C15 C20 -148.8(4) . . . . ?
N2 C6 C7 N1 -8.9(4) . . . . ?
N2 C6 C7 C15 111.9(3) . . . . ?
N2 C6 C9 C10 44.6(5) . . . . ?
N2 C6 C9 C14 -137.6(3) . . . . ?
C1 N1 C5 N2 173.3(3) . . . . ?
C1 N1 C5 C4 -6.0(5) . . . . ?
C1 N1 C7 C6 -168.8(3) . . . . ?
C1 N1 C7 C15 71.2(4) . . . . ?
C1 C2 C3 C4 0.4(6) . . . . ?
C1 C2 C3 C8 -177.9(3) . . . . ?
C2 C3 C4 C5 0.6(5) . . . . ?
C2 C3 C8 O2 174.5(4) . . . . ?
C2 C3 C8 O3 -3.9(5) . . . . ?
C3 C4 C5 N1 1.9(5) . . . . ?
C3 C4 C5 N2 -177.1(4) . . . . ?
C4 C3 C8 O2 -3.9(6) . . . . ?
C4 C3 C8 O3 177.7(3) . . . . ?
C5 N1 C1 O1 -172.1(3) . . . . ?
C5 N1 C1 C2 6.7(5) . . . . ?
C5 N1 C7 C6 7.6(4) . . . . ?
C5 N1 C7 C15 -112.5(3) . . . . ?
C5 N2 C6 C7 8.0(4) . . . . ?
C5 N2 C6 C9 -114.9(3) . . . . ?
C6 N2 C5 N1 -3.6(4) . . . . ?
C6 N2 C5 C4 175.6(3) . . . . ?
C6 C7 C15 C16 -76.7(4) . . . . ?
C6 C7 C15 C20 96.6(4) . . . . ?
C6 C9 C10 C11 177.5(4) . . . . ?
C6 C9 C14 C13 -176.3(4) . . . . ?
C7 N1 C1 O1 3.7(5) . . . . ?
C7 N1 C1 C2 -177.5(3) . . . . ?
C7 N1 C5 N2 -3.0(4) . . . . ?
C7 N1 C5 C4 177.8(3) . . . . ?
C7 C6 C9 C10 -73.1(5) . . . . ?
C7 C6 C9 C14 104.8(4) . . . . ?
C7 C15 C16 C17 172.3(3) . . . . ?
C7 C15 C20 C19 -172.6(4) . . . . ?
C8 C3 C4 C5 179.0(3) . . . . ?
C9 C6 C7 N1 114.5(3) . . . . ?
C9 C6 C7 C15 -124.7(4) . . . . ?
C9 C10 C11 C12 -0.7(7) . . . . ?
C10 C9 C14 C13 1.6(6) . . . . ?
C10 C11 C12 C13 0.6(7) . . . . ?
C11 C12 C13 C14 0.6(8) . . . . ?
C12 C13 C14 C9 -1.7(7) . . . . ?
C14 C9 C10 C11 -0.4(6) . . . . ?
C15 C16 C17 C18 0.4(6) . . . . ?
C16 C15 C20 C19 0.9(7) . . . . ?
C16 C17 C18 C19 0.5(7) . . . . ?
C17 C18 C19 C20 -0.7(7) . . . . ?
C18 C19 C20 C15 0.0(7) . . . . ?
C20 C15 C16 C17 -1.1(6) . . . . ?

_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_190801_s2_wzy_2
_database_code_depnum_ccdc_archive 'CCDC 2043201'
loop_
_audit_author_name
_audit_author_address
'Xiaoyun Ran'
;Xihua University
China
;
_audit_update_record             
;
2020-11-09 deposited with the CCDC.	2021-04-26 downloaded from the CCDC.
;
_audit_creation_date             2019-08-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C23 H20 N2 O4'
_chemical_formula_sum            'C23 H20 N2 O4'
_chemical_formula_weight         388.41
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         c12h12n2o3
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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   10.1065(14)
_cell_length_b                   10.7913(11)
_cell_length_c                   10.2229(13)
_cell_angle_alpha                90
_cell_angle_beta                 111.825(16)
_cell_angle_gamma                90
_cell_volume                     1035.0(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1076
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.8950
_cell_measurement_theta_min      4.0220
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.970
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67624
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0556
_diffrn_reflns_av_unetI/netI     0.1143
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            4390
_diffrn_reflns_point_group_measured_fraction_full 0.771
_diffrn_reflns_point_group_measured_fraction_max 0.752
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_min         2.858
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0874
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   -5.00   22.30   0.7000   27.5000
omega____ theta____ kappa____ phi______ frames
    -      -14.8106  -99.0000   90.0000 39

#__ type_ start__ end____ width___ exp.time_
  2 omega  -80.00    0.50   0.7000   27.5000
omega____ theta____ kappa____ phi______ frames
    -      -14.8106  -57.0000  -90.0000 115

#__ type_ start__ end____ width___ exp.time_
  3 omega  -84.00    6.30   0.7000   27.5000
omega____ theta____ kappa____ phi______ frames
    -      -14.8106  -19.0000  -30.0000 129
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0274420000
_diffrn_orient_matrix_UB_12      0.0025389000
_diffrn_orient_matrix_UB_13      -0.0545395000
_diffrn_orient_matrix_UB_21      -0.0684739000
_diffrn_orient_matrix_UB_22      0.0161898000
_diffrn_orient_matrix_UB_23      -0.0489911000
_diffrn_orient_matrix_UB_31      0.0163547000
_diffrn_orient_matrix_UB_32      0.0636606000
_diffrn_orient_matrix_UB_33      0.0146355000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.432
_reflns_Friedel_fraction_full    0.518
_reflns_Friedel_fraction_max     0.481
_reflns_number_gt                1646
_reflns_number_total             3191
_reflns_odcompleteness_completeness 99.55
_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, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details 
;
 Flack x determined using 451 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.8(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.833
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         3191
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1030
_refine_ls_R_factor_gt           0.0571
_refine_ls_restrained_S_all      0.832
_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)+(0.0550P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1202
_refine_ls_wR_factor_ref         0.1324
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6), C7(H7)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C11(H11), C12(H12), C13(H13), C14(H14), C15(H15), C17(H17),
 C18(H18), C19(H19), C20(H20), C21(H21)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C23(H23A,H23B,H23C)
;
_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 0.3338(4) 0.0225(3) 0.9100(4) 0.0552(10) Uani 1 1 d . . . . .
O2 O 0.0362(6) 0.2003(6) 0.3313(5) 0.134(2) Uani 1 1 d . . . . .
O3 O 0.0315(5) 0.0079(5) 0.4017(5) 0.1057(18) Uani 1 1 d . . . . .
O4 O 0.4158(5) 0.4828(4) 0.5706(4) 0.0713(12) Uani 1 1 d . . . . .
N1 N 0.4097(5) 0.1784(4) 0.8071(4) 0.0414(11) Uani 1 1 d . . . . .
N2 N 0.5064(4) 0.3438(4) 0.7457(4) 0.0422(11) Uani 1 1 d . . . . .
C1 C 0.3205(6) 0.0816(5) 0.8036(6) 0.0470(14) Uani 1 1 d . . . . .
C2 C 0.2094(6) 0.0639(5) 0.6659(6) 0.0525(15) Uani 1 1 d . . . . .
H2 H 0.1470 -0.0026 0.6513 0.063 Uiso 1 1 calc R . . . .
C3 C 0.1951(6) 0.1424(5) 0.5585(6) 0.0489(14) Uani 1 1 d . . . . .
C4 C 0.2864(6) 0.2450(5) 0.5722(5) 0.0499(14) Uani 1 1 d . . . . .
H4 H 0.2728 0.3001 0.4984 0.060 Uiso 1 1 calc R . . . .
C5 C 0.3948(5) 0.2591(5) 0.6988(5) 0.0409(13) Uani 1 1 d . . . . .
C6 C 0.6171(5) 0.2999(5) 0.8792(5) 0.0439(14) Uani 1 1 d . . . . .
H6 H 0.6508 0.3700 0.9441 0.053 Uiso 1 1 calc R . . . .
C7 C 0.5313(5) 0.2102(5) 0.9362(5) 0.0404(13) Uani 1 1 d . . . . .
H7 H 0.5882 0.1355 0.9726 0.049 Uiso 1 1 calc R . . . .
C8 C 0.0765(7) 0.1217(8) 0.4161(7) 0.074(2) Uani 1 1 d . . . . .
C9 C -0.0811(9) -0.0261(10) 0.2696(8) 0.143(4) Uani 1 1 d . . . . .
H9A H -0.0591 0.0056 0.1923 0.214 Uiso 1 1 calc GR . . . .
H9B H -0.1699 0.0084 0.2664 0.214 Uiso 1 1 calc GR . . . .
H9C H -0.0889 -0.1147 0.2628 0.214 Uiso 1 1 calc GR . . . .
C10 C 0.7422(6) 0.2392(5) 0.8592(6) 0.0481(14) Uani 1 1 d . . . . .
C11 C 0.7364(6) 0.1812(6) 0.7387(6) 0.0582(16) Uani 1 1 d . . . . .
H11 H 0.6522 0.1843 0.6598 0.070 Uiso 1 1 calc R . . . .
C12 C 0.8514(8) 0.1181(7) 0.7304(8) 0.080(2) Uani 1 1 d . . . . .
H12 H 0.8447 0.0784 0.6475 0.096 Uiso 1 1 calc R . . . .
C13 C 0.9788(8) 0.1148(8) 0.8490(10) 0.095(3) Uani 1 1 d . . . . .
H13 H 1.0576 0.0728 0.8452 0.114 Uiso 1 1 calc R . . . .
C14 C 0.9865(7) 0.1725(8) 0.9682(9) 0.095(3) Uani 1 1 d . . . . .
H14 H 1.0705 0.1690 1.0472 0.114 Uiso 1 1 calc R . . . .
C15 C 0.8708(6) 0.2371(6) 0.9745(7) 0.0709(19) Uani 1 1 d . . . . .
H15 H 0.8789 0.2794 1.0564 0.085 Uiso 1 1 calc R . . . .
C16 C 0.4883(6) 0.2638(5) 1.0489(5) 0.0418(13) Uani 1 1 d . . . . .
C17 C 0.3638(6) 0.3258(6) 1.0228(6) 0.0606(16) Uani 1 1 d . . . . .
H17 H 0.2991 0.3305 0.9303 0.073 Uiso 1 1 calc R . . . .
C18 C 0.3293(8) 0.3818(6) 1.1267(8) 0.075(2) Uani 1 1 d . . . . .
H18 H 0.2426 0.4225 1.1047 0.090 Uiso 1 1 calc R . . . .
C19 C 0.4247(10) 0.3765(6) 1.2630(8) 0.081(2) Uani 1 1 d . . . . .
H19 H 0.4042 0.4156 1.3343 0.097 Uiso 1 1 calc R . . . .
C20 C 0.5494(9) 0.3142(7) 1.2937(7) 0.080(2) Uani 1 1 d . . . . .
H20 H 0.6127 0.3089 1.3868 0.096 Uiso 1 1 calc R . . . .
C21 C 0.5835(6) 0.2583(6) 1.1882(6) 0.0613(17) Uani 1 1 d . . . . .
H21 H 0.6700 0.2172 1.2104 0.074 Uiso 1 1 calc R . . . .
C22 C 0.5152(6) 0.4521(5) 0.6771(6) 0.0505(15) Uani 1 1 d . . . . .
C23 C 0.6485(7) 0.5268(5) 0.7410(6) 0.0654(17) Uani 1 1 d . . . . .
H23A H 0.6446 0.5973 0.6825 0.098 Uiso 1 1 calc GR . . . .
H23B H 0.7294 0.4766 0.7485 0.098 Uiso 1 1 calc GR . . . .
H23C H 0.6570 0.5543 0.8331 0.098 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 1.224(6) . ?
O2 C8 1.172(8) . ?
O3 C8 1.299(8) . ?
O3 C9 1.453(7) . ?
O4 C22 1.221(6) . ?
N1 C1 1.371(6) . ?
N1 C5 1.372(6) . ?
N1 C7 1.471(6) . ?
N2 C5 1.391(6) . ?
N2 C6 1.485(6) . ?
N2 C22 1.383(7) . ?
C1 C2 1.451(7) . ?
C2 H2 0.9300 . ?
C2 C3 1.351(7) . ?
C3 C4 1.414(7) . ?
C3 C8 1.520(8) . ?
C4 H4 0.9300 . ?
C4 C5 1.358(7) . ?
C6 H6 0.9800 . ?
C6 C7 1.551(7) . ?
C6 C10 1.504(7) . ?
C7 H7 0.9800 . ?
C7 C16 1.491(6) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.363(7) . ?
C10 C15 1.392(7) . ?
C11 H11 0.9300 . ?
C11 C12 1.376(8) . ?
C12 H12 0.9300 . ?
C12 C13 1.403(9) . ?
C13 H13 0.9300 . ?
C13 C14 1.345(9) . ?
C14 H14 0.9300 . ?
C14 C15 1.383(9) . ?
C15 H15 0.9300 . ?
C16 C17 1.361(7) . ?
C16 C21 1.392(7) . ?
C17 H17 0.9300 . ?
C17 C18 1.375(7) . ?
C18 H18 0.9300 . ?
C18 C19 1.370(9) . ?
C19 H19 0.9300 . ?
C19 C20 1.358(9) . ?
C20 H20 0.9300 . ?
C20 C21 1.387(8) . ?
C21 H21 0.9300 . ?
C22 C23 1.495(8) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?

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
C8 O3 C9 117.6(6) . . ?
C1 N1 C5 126.1(5) . . ?
C1 N1 C7 121.5(4) . . ?
C5 N1 C7 112.3(4) . . ?
C5 N2 C6 110.1(4) . . ?
C22 N2 C5 125.3(4) . . ?
C22 N2 C6 124.5(4) . . ?
O1 C1 N1 121.3(5) . . ?
O1 C1 C2 125.7(5) . . ?
N1 C1 C2 112.9(5) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 C1 121.1(5) . . ?
C3 C2 H2 119.5 . . ?
C2 C3 C4 122.8(5) . . ?
C2 C3 C8 119.6(5) . . ?
C4 C3 C8 117.6(5) . . ?
C3 C4 H4 121.7 . . ?
C5 C4 C3 116.6(5) . . ?
C5 C4 H4 121.7 . . ?
N1 C5 N2 107.9(4) . . ?
C4 C5 N1 120.4(5) . . ?
C4 C5 N2 131.7(5) . . ?
N2 C6 H6 109.3 . . ?
N2 C6 C7 102.1(4) . . ?
N2 C6 C10 113.5(4) . . ?
C7 C6 H6 109.3 . . ?
C10 C6 H6 109.3 . . ?
C10 C6 C7 113.2(4) . . ?
N1 C7 C6 101.9(4) . . ?
N1 C7 H7 109.0 . . ?
N1 C7 C16 113.4(4) . . ?
C6 C7 H7 109.0 . . ?
C16 C7 C6 114.4(4) . . ?
C16 C7 H7 109.0 . . ?
O2 C8 O3 126.2(7) . . ?
O2 C8 C3 122.4(7) . . ?
O3 C8 C3 111.4(6) . . ?
O3 C9 H9A 109.5 . . ?
O3 C9 H9B 109.5 . . ?
O3 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C6 124.5(5) . . ?
C11 C10 C15 118.1(5) . . ?
C15 C10 C6 117.3(5) . . ?
C10 C11 H11 119.1 . . ?
C10 C11 C12 121.9(6) . . ?
C12 C11 H11 119.1 . . ?
C11 C12 H12 120.5 . . ?
C11 C12 C13 119.0(6) . . ?
C13 C12 H12 120.5 . . ?
C12 C13 H13 120.1 . . ?
C14 C13 C12 119.7(7) . . ?
C14 C13 H13 120.1 . . ?
C13 C14 H14 119.6 . . ?
C13 C14 C15 120.7(7) . . ?
C15 C14 H14 119.6 . . ?
C10 C15 H15 119.8 . . ?
C14 C15 C10 120.5(6) . . ?
C14 C15 H15 119.8 . . ?
C17 C16 C7 123.5(5) . . ?
C17 C16 C21 117.3(5) . . ?
C21 C16 C7 119.0(5) . . ?
C16 C17 H17 118.5 . . ?
C16 C17 C18 123.1(6) . . ?
C18 C17 H17 118.5 . . ?
C17 C18 H18 120.6 . . ?
C19 C18 C17 118.9(7) . . ?
C19 C18 H18 120.6 . . ?
C18 C19 H19 120.1 . . ?
C20 C19 C18 119.8(7) . . ?
C20 C19 H19 120.1 . . ?
C19 C20 H20 119.6 . . ?
C19 C20 C21 120.9(7) . . ?
C21 C20 H20 119.6 . . ?
C16 C21 H21 120.0 . . ?
C20 C21 C16 120.0(6) . . ?
C20 C21 H21 120.0 . . ?
O4 C22 N2 119.6(5) . . ?
O4 C22 C23 123.5(6) . . ?
N2 C22 C23 116.8(5) . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 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 173.0(5) . . . . ?
N1 C1 C2 C3 -3.8(7) . . . . ?
N1 C7 C16 C17 -26.5(7) . . . . ?
N1 C7 C16 C21 158.0(5) . . . . ?
N2 C6 C7 N1 22.1(4) . . . . ?
N2 C6 C7 C16 -100.6(4) . . . . ?
N2 C6 C10 C11 -26.7(7) . . . . ?
N2 C6 C10 C15 156.6(5) . . . . ?
C1 N1 C5 N2 179.5(4) . . . . ?
C1 N1 C5 C4 -2.0(7) . . . . ?
C1 N1 C7 C6 166.7(4) . . . . ?
C1 N1 C7 C16 -69.9(6) . . . . ?
C1 C2 C3 C4 0.4(8) . . . . ?
C1 C2 C3 C8 -179.4(5) . . . . ?
C2 C3 C4 C5 2.6(8) . . . . ?
C2 C3 C8 O2 160.6(8) . . . . ?
C2 C3 C8 O3 -21.2(8) . . . . ?
C3 C4 C5 N1 -1.9(7) . . . . ?
C3 C4 C5 N2 176.2(5) . . . . ?
C4 C3 C8 O2 -19.2(10) . . . . ?
C4 C3 C8 O3 159.0(5) . . . . ?
C5 N1 C1 O1 -172.2(5) . . . . ?
C5 N1 C1 C2 4.7(7) . . . . ?
C5 N1 C7 C6 -16.2(5) . . . . ?
C5 N1 C7 C16 107.2(5) . . . . ?
C5 N2 C6 C7 -22.6(5) . . . . ?
C5 N2 C6 C10 99.6(5) . . . . ?
C5 N2 C22 O4 4.3(8) . . . . ?
C5 N2 C22 C23 -176.5(5) . . . . ?
C6 N2 C5 N1 13.4(5) . . . . ?
C6 N2 C5 C4 -164.9(5) . . . . ?
C6 N2 C22 O4 -177.1(5) . . . . ?
C6 N2 C22 C23 2.1(7) . . . . ?
C6 C7 C16 C17 89.7(6) . . . . ?
C6 C7 C16 C21 -85.7(6) . . . . ?
C6 C10 C11 C12 -174.4(6) . . . . ?
C6 C10 C15 C14 173.7(6) . . . . ?
C7 N1 C1 O1 4.4(7) . . . . ?
C7 N1 C1 C2 -178.6(4) . . . . ?
C7 N1 C5 N2 2.6(5) . . . . ?
C7 N1 C5 C4 -178.8(4) . . . . ?
C7 C6 C10 C11 89.0(6) . . . . ?
C7 C6 C10 C15 -87.7(6) . . . . ?
C7 C16 C17 C18 -175.6(5) . . . . ?
C7 C16 C21 C20 176.1(5) . . . . ?
C8 C3 C4 C5 -177.6(5) . . . . ?
C9 O3 C8 O2 -1.1(12) . . . . ?
C9 O3 C8 C3 -179.3(6) . . . . ?
C10 C6 C7 N1 -100.2(5) . . . . ?
C10 C6 C7 C16 137.0(4) . . . . ?
C10 C11 C12 C13 -0.8(10) . . . . ?
C11 C10 C15 C14 -3.2(9) . . . . ?
C11 C12 C13 C14 0.2(11) . . . . ?
C12 C13 C14 C15 -1.1(12) . . . . ?
C13 C14 C15 C10 2.7(11) . . . . ?
C15 C10 C11 C12 2.3(9) . . . . ?
C16 C17 C18 C19 0.7(10) . . . . ?
C17 C16 C21 C20 0.3(8) . . . . ?
C17 C18 C19 C20 -1.6(10) . . . . ?
C18 C19 C20 C21 1.8(11) . . . . ?
C19 C20 C21 C16 -1.2(10) . . . . ?
C21 C16 C17 C18 -0.1(9) . . . . ?
C22 N2 C5 N1 -167.9(5) . . . . ?
C22 N2 C5 C4 13.8(8) . . . . ?
C22 N2 C6 C7 158.7(4) . . . . ?
C22 N2 C6 C10 -79.1(6) . . . . ?

_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_191122_s2_wzy_rxy
_database_code_depnum_ccdc_archive 'CCDC 2043204'
loop_
_audit_author_name
_audit_author_address
'Xiaoyun Ran'
;Xihua University
China
;
_audit_update_record             
;
2020-11-09 deposited with the CCDC.	2021-04-26 downloaded from the CCDC.
;
_audit_creation_date             2019-11-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C21 H16 Br2 N2 O3'
_chemical_formula_sum            'C21 H16 Br2 N2 O3'
_chemical_formula_weight         504.18
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         c12h12n2o2
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'
Br Br -0.2901 2.4595 '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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   9.0188(9)
_cell_length_b                   11.8068(9)
_cell_length_c                   19.0898(18)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2032.7(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3332
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.5350
_cell_measurement_theta_min      3.5170
_shelx_estimated_absorpt_T_max   0.434
_shelx_estimated_absorpt_T_min   0.334
_exptl_absorpt_coefficient_mu    4.012
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54628
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.647
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1000
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0907
_diffrn_reflns_av_unetI/netI     0.0978
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            15533
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         3.036
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0874
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   -2.00   75.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -       16.8419   38.0000    0.0000 77

#__ type_ start__ end____ width___ exp.time_
  2 omega  -11.00   21.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.8106  -99.0000  -30.0000 32

#__ type_ start__ end____ width___ exp.time_
  3 omega  -40.00   32.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -       16.8419  -57.0000  -30.0000 72

#__ type_ start__ end____ width___ exp.time_
  4 omega  -41.00   52.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.8106   77.0000 -150.0000 93

#__ type_ start__ end____ width___ exp.time_
  5 omega  -82.00   12.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.8106  -77.0000   90.0000 94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0206003000
_diffrn_orient_matrix_UB_12      0.0017351000
_diffrn_orient_matrix_UB_13      0.0358326000
_diffrn_orient_matrix_UB_21      0.0708187000
_diffrn_orient_matrix_UB_22      -0.0222298000
_diffrn_orient_matrix_UB_23      -0.0086386000
_diffrn_orient_matrix_UB_31      0.0275562000
_diffrn_orient_matrix_UB_32      0.0557459000
_diffrn_orient_matrix_UB_33      -0.0045317000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.737
_reflns_Friedel_fraction_full    0.987
_reflns_Friedel_fraction_max     0.980
_reflns_number_gt                2584
_reflns_number_total             4116
_reflns_odcompleteness_completeness 99.67
_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, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_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         0.693
_refine_diff_density_min         -0.600
_refine_diff_density_rms         0.086
_refine_ls_abs_structure_details 
;
 Flack x determined using 728 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.008(11)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.904
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         4116
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1083
_refine_ls_R_factor_gt           0.0591
_refine_ls_restrained_S_all      0.904
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1409
_refine_ls_wR_factor_ref         0.1783
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5), C6(H6)
2.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C13(H13), C14(H14), C15(H15), C17(H17), C18(H18),
 C19(H19), C20(H20), C21(H21)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   mixed
_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
Br1 Br 0.80513(14) 0.75555(9) 0.55857(6) 0.0624(4) Uani 1 1 d . . . . .
Br2 Br 0.24295(15) 0.60260(11) 0.65909(7) 0.0715(5) Uani 1 1 d . . . . .
O1 O 0.3570(8) 0.3885(6) 0.5828(4) 0.0500(18) Uani 1 1 d . . . . .
O2 O 0.4556(11) 0.8569(6) 0.6095(4) 0.062(2) Uani 1 1 d . . . . .
O3 O 0.5360(10) 0.7732(6) 0.7055(4) 0.063(2) Uani 1 1 d . . . . .
N1 N 0.5623(10) 0.4660(6) 0.5338(4) 0.0347(19) Uani 1 1 d . . . . .
N2 N 0.7776(12) 0.5090(8) 0.4867(5) 0.043(2) Uani 1 1 d . . . . .
H2 H 0.822(10) 0.552(7) 0.470(4) 0.01(2) Uiso 1 1 d . . . . .
C1 C 0.6549(12) 0.6467(8) 0.5635(5) 0.039(2) Uani 1 1 d . . . . .
C2 C 0.5244(12) 0.6629(8) 0.6047(6) 0.040(2) Uani 1 1 d . . . . .
C3 C 0.4215(12) 0.5807(9) 0.6092(5) 0.043(2) Uani 1 1 d . . . . .
C4 C 0.4367(12) 0.4715(8) 0.5768(5) 0.038(2) Uani 1 1 d . . . . .
C5 C 0.6033(13) 0.3634(8) 0.4950(5) 0.039(2) Uani 1 1 d . . . . .
H5 H 0.5198 0.3376 0.4663 0.046 Uiso 1 1 calc R . . . .
C6 C 0.7309(12) 0.4107(7) 0.4470(5) 0.041(2) Uani 1 1 d . . . . .
H6 H 0.8122 0.3556 0.4452 0.049 Uiso 1 1 calc R . . . .
C7 C 0.6681(13) 0.5470(9) 0.5296(5) 0.041(3) Uani 1 1 d . . . . .
C8 C 0.4991(12) 0.7748(8) 0.6388(5) 0.041(3) Uani 1 1 d . . . . .
C9 C 0.513(2) 0.8788(11) 0.7443(8) 0.087(5) Uani 1 1 d . . . . .
H9A H 0.5788 0.9360 0.7267 0.131 Uiso 1 1 calc GR . . . .
H9B H 0.5327 0.8662 0.7931 0.131 Uiso 1 1 calc GR . . . .
H9C H 0.4122 0.9033 0.7386 0.131 Uiso 1 1 calc GR . . . .
C10 C 0.6532(12) 0.2711(8) 0.5425(5) 0.044(3) Uani 1 1 d . . . . .
C11 C 0.7373(17) 0.2915(10) 0.6002(6) 0.064(3) Uani 1 1 d . . . . .
H11 H 0.7639 0.3653 0.6116 0.076 Uiso 1 1 calc R . . . .
C12 C 0.7839(18) 0.2014(14) 0.6424(8) 0.090(5) Uani 1 1 d . . . . .
H12 H 0.8393 0.2156 0.6825 0.109 Uiso 1 1 calc R . . . .
C13 C 0.748(2) 0.0928(13) 0.6249(10) 0.092(5) Uani 1 1 d . . . . .
H13 H 0.7785 0.0329 0.6531 0.111 Uiso 1 1 calc R . . . .
C14 C 0.6691(19) 0.0730(10) 0.5668(10) 0.082(5) Uani 1 1 d . . . . .
H14 H 0.6454 -0.0013 0.5552 0.099 Uiso 1 1 calc R . . . .
C15 C 0.6218(15) 0.1594(9) 0.5239(7) 0.059(3) Uani 1 1 d . . . . .
H15 H 0.5697 0.1436 0.4831 0.071 Uiso 1 1 calc R . . . .
C16 C 0.6816(12) 0.4388(9) 0.3732(5) 0.045(3) Uani 1 1 d . . . . .
C17 C 0.6139(16) 0.5399(11) 0.3579(6) 0.062(3) Uani 1 1 d . . . . .
H17 H 0.5970 0.5924 0.3933 0.074 Uiso 1 1 calc R . . . .
C18 C 0.5712(19) 0.5637(13) 0.2909(9) 0.086(5) Uani 1 1 d . . . . .
H18 H 0.5273 0.6329 0.2804 0.103 Uiso 1 1 calc R . . . .
C19 C 0.5936(19) 0.484(2) 0.2386(8) 0.095(6) Uani 1 1 d . . . . .
H19 H 0.5636 0.5001 0.1930 0.114 Uiso 1 1 calc R . . . .
C20 C 0.6582(19) 0.3845(16) 0.2532(8) 0.089(5) Uani 1 1 d . . . . .
H20 H 0.6728 0.3313 0.2179 0.107 Uiso 1 1 calc R . . . .
C21 C 0.7032(16) 0.3611(12) 0.3214(6) 0.069(4) Uani 1 1 d . . . . .
H21 H 0.7482 0.2922 0.3317 0.083 Uiso 1 1 calc R . . . .


_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 C1 1.870(11) . ?
Br2 C3 1.889(10) . ?
O1 C4 1.221(12) . ?
O2 C8 1.186(11) . ?
O3 C8 1.316(12) . ?
O3 C9 1.465(14) . ?
N1 C4 1.400(13) . ?
N1 C5 1.467(12) . ?
N1 C7 1.354(13) . ?
N2 C6 1.449(12) . ?
N2 C7 1.359(14) . ?
C1 C2 1.428(15) . ?
C1 C7 1.348(14) . ?
C2 C3 1.346(14) . ?
C2 C8 1.491(14) . ?
C3 C4 1.436(14) . ?
C5 C6 1.574(14) . ?
C5 C10 1.489(13) . ?
C6 C16 1.513(14) . ?
C10 C11 1.358(16) . ?
C10 C15 1.394(14) . ?
C11 C12 1.399(17) . ?
C12 C13 1.36(2) . ?
C13 C14 1.34(2) . ?
C14 C15 1.376(19) . ?
C16 C17 1.372(16) . ?
C16 C21 1.363(15) . ?
C17 C18 1.365(18) . ?
C18 C19 1.38(2) . ?
C19 C20 1.34(2) . ?
C20 C21 1.39(2) . ?

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
C8 O3 C9 116.2(9) . . ?
C4 N1 C5 122.6(8) . . ?
C7 N1 C4 124.9(9) . . ?
C7 N1 C5 112.0(9) . . ?
C7 N2 C6 111.7(10) . . ?
C2 C1 Br1 122.2(7) . . ?
C7 C1 Br1 120.8(8) . . ?
C7 C1 C2 117.0(10) . . ?
C1 C2 C8 119.1(10) . . ?
C3 C2 C1 120.4(9) . . ?
C3 C2 C8 120.4(10) . . ?
C2 C3 Br2 121.4(8) . . ?
C2 C3 C4 123.6(10) . . ?
C4 C3 Br2 114.9(7) . . ?
O1 C4 N1 119.7(9) . . ?
O1 C4 C3 128.6(10) . . ?
N1 C4 C3 111.8(9) . . ?
N1 C5 C6 100.7(7) . . ?
N1 C5 C10 111.9(8) . . ?
C10 C5 C6 113.2(9) . . ?
N2 C6 C5 101.0(8) . . ?
N2 C6 C16 113.4(8) . . ?
C16 C6 C5 113.9(9) . . ?
N1 C7 N2 108.3(9) . . ?
C1 C7 N1 121.7(10) . . ?
C1 C7 N2 129.9(10) . . ?
O2 C8 O3 123.5(10) . . ?
O2 C8 C2 124.6(9) . . ?
O3 C8 C2 111.8(9) . . ?
C11 C10 C5 122.2(9) . . ?
C11 C10 C15 119.2(11) . . ?
C15 C10 C5 118.4(10) . . ?
C10 C11 C12 120.0(12) . . ?
C13 C12 C11 120.1(15) . . ?
C14 C13 C12 119.6(14) . . ?
C13 C14 C15 121.9(14) . . ?
C14 C15 C10 119.1(13) . . ?
C17 C16 C6 121.4(10) . . ?
C21 C16 C6 119.0(11) . . ?
C21 C16 C17 119.6(11) . . ?
C18 C17 C16 120.3(13) . . ?
C17 C18 C19 119.6(15) . . ?
C20 C19 C18 120.6(14) . . ?
C19 C20 C21 119.6(15) . . ?
C16 C21 C20 120.3(14) . . ?

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
Br1 C1 C2 C3 -177.3(8) . . . . ?
Br1 C1 C2 C8 6.5(13) . . . . ?
Br1 C1 C7 N1 178.5(7) . . . . ?
Br1 C1 C7 N2 -2.8(16) . . . . ?
Br2 C3 C4 O1 -7.7(14) . . . . ?
Br2 C3 C4 N1 172.6(7) . . . . ?
N1 C5 C6 N2 23.0(9) . . . . ?
N1 C5 C6 C16 -98.9(9) . . . . ?
N1 C5 C10 C11 -38.6(15) . . . . ?
N1 C5 C10 C15 146.5(10) . . . . ?
N2 C6 C16 C17 -32.4(15) . . . . ?
N2 C6 C16 C21 148.6(11) . . . . ?
C1 C2 C3 Br2 -176.6(8) . . . . ?
C1 C2 C3 C4 2.8(16) . . . . ?
C1 C2 C8 O2 77.7(15) . . . . ?
C1 C2 C8 O3 -100.0(11) . . . . ?
C2 C1 C7 N1 0.4(15) . . . . ?
C2 C1 C7 N2 179.1(10) . . . . ?
C2 C3 C4 O1 172.9(11) . . . . ?
C2 C3 C4 N1 -6.8(14) . . . . ?
C3 C2 C8 O2 -98.5(15) . . . . ?
C3 C2 C8 O3 83.8(13) . . . . ?
C4 N1 C5 C6 170.4(9) . . . . ?
C4 N1 C5 C10 -69.0(13) . . . . ?
C4 N1 C7 N2 175.6(9) . . . . ?
C4 N1 C7 C1 -5.4(15) . . . . ?
C5 N1 C4 O1 0.0(15) . . . . ?
C5 N1 C4 C3 179.7(8) . . . . ?
C5 N1 C7 N2 3.3(11) . . . . ?
C5 N1 C7 C1 -177.7(9) . . . . ?
C5 C6 C16 C17 82.4(13) . . . . ?
C5 C6 C16 C21 -96.6(12) . . . . ?
C5 C10 C11 C12 -178.7(12) . . . . ?
C5 C10 C15 C14 179.1(12) . . . . ?
C6 N2 C7 N1 14.0(12) . . . . ?
C6 N2 C7 C1 -164.8(10) . . . . ?
C6 C5 C10 C11 74.4(13) . . . . ?
C6 C5 C10 C15 -100.5(12) . . . . ?
C6 C16 C17 C18 179.6(12) . . . . ?
C6 C16 C21 C20 179.6(12) . . . . ?
C7 N1 C4 O1 -171.5(10) . . . . ?
C7 N1 C4 C3 8.1(14) . . . . ?
C7 N1 C5 C6 -17.1(10) . . . . ?
C7 N1 C5 C10 103.5(10) . . . . ?
C7 N2 C6 C5 -23.6(11) . . . . ?
C7 N2 C6 C16 98.6(11) . . . . ?
C7 C1 C2 C3 0.8(15) . . . . ?
C7 C1 C2 C8 -175.4(9) . . . . ?
C8 C2 C3 Br2 -0.4(14) . . . . ?
C8 C2 C3 C4 178.9(9) . . . . ?
C9 O3 C8 O2 3.3(17) . . . . ?
C9 O3 C8 C2 -179.0(11) . . . . ?
C10 C5 C6 N2 -96.7(9) . . . . ?
C10 C5 C6 C16 141.5(9) . . . . ?
C10 C11 C12 C13 2(2) . . . . ?
C11 C10 C15 C14 4.0(18) . . . . ?
C11 C12 C13 C14 0(2) . . . . ?
C12 C13 C14 C15 0(3) . . . . ?
C13 C14 C15 C10 -2(2) . . . . ?
C15 C10 C11 C12 -3.8(18) . . . . ?
C16 C17 C18 C19 1(2) . . . . ?
C17 C16 C21 C20 1(2) . . . . ?
C17 C18 C19 C20 -1(2) . . . . ?
C18 C19 C20 C21 0(2) . . . . ?
C19 C20 C21 C16 0(2) . . . . ?
C21 C16 C17 C18 -1(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
