# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 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 
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data_ycs20220328chen_0m
_database_code_depnum_ccdc_archive 'CCDC 2181911'
loop_
_audit_author_name
_audit_author_address
'Kai zhangkai'
;Jiangsu Normal University
China
;
_audit_update_record             
;
2022-06-26 deposited with the CCDC.	2022-09-12 downloaded from the CCDC.
;
_audit_creation_date             2022-06-25
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        zk
_chemical_formula_moiety         'C22 H18 Br N O5'
_chemical_formula_sum            'C22 H18 Br N O5'
_chemical_formula_weight         456.28
_chemical_absolute_configuration rm
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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      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                   8.738(6)
_cell_length_b                   14.001(10)
_cell_length_c                   8.854(6)
_cell_angle_alpha                90
_cell_angle_beta                 109.928(9)
_cell_angle_gamma                90
_cell_volume                     1018.3(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2796
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      25.431
_cell_measurement_theta_min      2.447
_shelx_estimated_absorpt_T_max   0.684
_shelx_estimated_absorpt_T_min   0.684
_exptl_absorpt_coefficient_mu    2.052
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4999
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/3 (Bruker,2014/3) was used for absorption correction.
wR2(int) was 0.1057 before and 0.0680 after correction.
The Ratio of minimum to maximum transmission is 0.6705.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.488
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0217
_diffrn_reflns_av_unetI/netI     0.0738
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            6231
_diffrn_reflns_point_group_measured_fraction_full 0.935
_diffrn_reflns_point_group_measured_fraction_max 0.888
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.878
_diffrn_reflns_theta_min         2.829
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.748
_reflns_Friedel_fraction_full    0.867
_reflns_Friedel_fraction_max     0.792
_reflns_number_gt                3144
_reflns_number_total             4333
_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 v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.367
_refine_diff_density_min         -0.372
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details 
;
 Flack x determined using 1110 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.054(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.983
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         4333
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.0679
_refine_ls_R_factor_gt           0.0473
_refine_ls_restrained_S_all      1.024
_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)+(0.0645P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1192
_refine_ls_wR_factor_ref         0.1297
_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. Restrained distances
 C21-C20
 1.54 with sigma of 0.02
 C20-C21
 1.54 with sigma of 0.02
3. Rigid bond restraints
 C20, C21
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
 C1, O1
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
 O4, C20
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
4. Uiso/Uaniso restraints and constraints
Uanis(O4) \\sim Ueq, Uanis(C20) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
5.a Ternary CH refined with riding coordinates:
 C8(H8)
5.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C20(H20A,H20B)
5.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C13(H13), C16(H16), C17(H17), C18(H18)
5.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C21(H21A,H21B,H21C)
5.e :
 C10(H10)
;
_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
Br1 Br 0.47698(8) 0.39665(7) 0.79849(7) 0.0752(3) Uani 1 1 d . . . . .
O2 O 0.3843(5) 0.3384(4) 0.1097(5) 0.0738(12) Uani 1 1 d . . . . .
O5 O 0.6138(6) 0.6109(3) 0.7139(6) 0.0706(12) Uani 1 1 d . . . . .
N1 N 0.5857(6) 0.6161(3) 0.4476(6) 0.0537(11) Uani 1 1 d . . . . .
O1 O 0.1622(5) 0.3256(4) 0.1904(7) 0.0886(16) Uani 1 1 d . U . . .
O3 O 1.0061(7) 0.5286(5) 0.8785(6) 0.0941(17) Uani 1 1 d . . . . .
C11 C 0.6599(7) 0.5920(4) 0.6038(7) 0.0517(13) Uani 1 1 d . . . . .
C2 C 0.4275(7) 0.3568(4) 0.2683(7) 0.0524(13) Uani 1 1 d . . . . .
C3 C 0.2959(6) 0.3492(4) 0.3177(8) 0.0583(14) Uani 1 1 d . . . . .
C4 C 0.5785(6) 0.3792(4) 0.3723(6) 0.0432(12) Uani 1 1 d . . . . .
H4 H 0.667079 0.382521 0.336931 0.052 Uiso 1 1 calc R U . . .
C5 C 0.3086(7) 0.3613(4) 0.4728(9) 0.0657(17) Uani 1 1 d . . . . .
H5 H 0.219611 0.353102 0.506509 0.079 Uiso 1 1 calc R U . . .
C12 C 0.6812(7) 0.5887(4) 0.3515(7) 0.0507(13) Uani 1 1 d . . . . .
C15 C 0.8220(6) 0.5438(4) 0.4482(6) 0.0473(11) Uani 1 1 d . . . . .
C7 C 0.5976(5) 0.3972(5) 0.5338(5) 0.0418(9) Uani 1 1 d . . . . .
C13 C 0.6518(10) 0.6031(5) 0.1915(8) 0.0700(19) Uani 1 1 d . . . . .
H13 H 0.559117 0.635446 0.128473 0.084 Uiso 1 1 calc R U . . .
C6 C 0.4628(6) 0.3869(5) 0.5810(6) 0.0499(12) Uani 1 1 d . . . . .
C9 C 0.8864(7) 0.3542(4) 0.6417(7) 0.0521(13) Uani 1 1 d . . . . .
C16 C 0.9331(8) 0.5122(5) 0.3830(8) 0.0628(15) Uani 1 1 d . . . . .
H16 H 1.027733 0.481533 0.446096 0.075 Uiso 1 1 calc R U . . .
C8 C 0.7646(6) 0.4257(3) 0.6474(6) 0.0471(12) Uani 1 1 d . . . . .
H8 H 0.760157 0.424913 0.756457 0.057 Uiso 1 1 calc R U . . .
C14 C 0.8102(6) 0.5303(4) 0.6130(6) 0.0490(12) Uani 1 1 d . . . . .
C17 C 0.9019(11) 0.5268(6) 0.2206(9) 0.081(2) Uani 1 1 d . . . . .
H17 H 0.978478 0.507569 0.175295 0.097 Uiso 1 1 calc R U . . .
C1 C 0.2144(9) 0.3181(6) 0.0542(10) 0.083(2) Uani 1 1 d . U . . .
H1A H 0.194089 0.254339 0.009088 0.099 Uiso 1 1 calc R U . . .
H1B H 0.156044 0.363538 -0.028046 0.099 Uiso 1 1 calc R U . . .
O4 O 1.0228(8) 0.6381(6) 0.7084(7) 0.132(3) Uani 1 1 d . U . . .
C19 C 0.9583(8) 0.5645(6) 0.7521(7) 0.0656(17) Uani 1 1 d . . . . .
C10 C 0.9741(8) 0.2926(5) 0.6376(9) 0.0690(17) Uani 1 1 d . . . . .
H10 H 1.044316 0.243395 0.634248 0.083 Uiso 1 1 calc R U . . .
C18 C 0.7619(11) 0.5687(5) 0.1260(9) 0.0743(19) Uani 1 1 d . . . . .
H18 H 0.740684 0.574053 0.016055 0.089 Uiso 1 1 calc R U . . .
C22 C 0.4216(9) 0.6499(5) 0.3828(10) 0.077(2) Uani 1 1 d . . . . .
H22A H 0.352514 0.599466 0.323673 0.115 Uiso 1 1 calc R U . . .
H22B H 0.416678 0.702840 0.312347 0.115 Uiso 1 1 calc R U . . .
H22C H 0.385633 0.670076 0.468743 0.115 Uiso 1 1 calc R U . . .
C20 C 1.1533(16) 0.7054(13) 0.8502(19) 0.153(5) Uani 1 1 d D U . . .
H20A H 1.147203 0.773325 0.827020 0.184 Uiso 1 1 calc R U . . .
H20B H 1.156280 0.692509 0.958756 0.184 Uiso 1 1 calc R U . . .
C21 C 1.2654(17) 0.6570(13) 0.8050(17) 0.169(7) Uani 1 1 d D U . . .
H21A H 1.276902 0.593459 0.848172 0.253 Uiso 1 1 calc R U . . .
H21B H 1.368248 0.689407 0.845044 0.253 Uiso 1 1 calc R U . . .
H21C H 1.230328 0.653929 0.689895 0.253 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
Br1 C6 1.892(5) . ?
O2 C2 1.349(7) . ?
O2 C1 1.424(8) . ?
O5 C11 1.205(7) . ?
N1 C11 1.355(8) . ?
N1 C12 1.432(8) . ?
N1 C22 1.431(8) . ?
O1 C3 1.359(8) . ?
O1 C1 1.432(10) . ?
O3 C19 1.167(9) . ?
C11 C14 1.550(8) . ?
C2 C3 1.367(8) . ?
C2 C4 1.363(8) . ?
C3 C5 1.350(9) . ?
C4 H4 0.9300 . ?
C4 C7 1.405(7) . ?
C5 H5 0.9300 . ?
C5 C6 1.408(9) . ?
C12 C15 1.388(8) . ?
C12 C13 1.365(9) . ?
C15 C16 1.361(8) . ?
C15 C14 1.510(7) . ?
C7 C6 1.386(6) . ?
C7 C8 1.516(7) . ?
C13 H13 0.9300 . ?
C13 C18 1.369(12) . ?
C9 C8 1.474(8) . ?
C9 C10 1.162(9) . ?
C16 H16 0.9300 . ?
C16 C17 1.385(10) . ?
C8 H8 0.9800 . ?
C8 C14 1.575(7) . ?
C14 C19 1.528(8) . ?
C17 H17 0.9300 . ?
C17 C18 1.357(12) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
O4 C19 1.295(10) . ?
O4 C20 1.670(16) . ?
C10 H10 0.9300 . ?
C18 H18 0.9300 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C21 1.359(13) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 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
C2 O2 C1 106.6(5) . . ?
C11 N1 C12 111.5(5) . . ?
C11 N1 C22 123.9(6) . . ?
C22 N1 C12 123.8(5) . . ?
C3 O1 C1 106.6(5) . . ?
O5 C11 N1 126.6(6) . . ?
O5 C11 C14 126.2(5) . . ?
N1 C11 C14 107.1(5) . . ?
O2 C2 C3 110.5(5) . . ?
O2 C2 C4 127.6(6) . . ?
C4 C2 C3 121.9(6) . . ?
O1 C3 C2 109.5(6) . . ?
C5 C3 O1 128.6(6) . . ?
C5 C3 C2 121.9(5) . . ?
C2 C4 H4 120.6 . . ?
C2 C4 C7 118.7(5) . . ?
C7 C4 H4 120.6 . . ?
C3 C5 H5 121.6 . . ?
C3 C5 C6 116.9(5) . . ?
C6 C5 H5 121.6 . . ?
C15 C12 N1 109.2(5) . . ?
C13 C12 N1 129.5(6) . . ?
C13 C12 C15 121.3(6) . . ?
C12 C15 C14 108.3(5) . . ?
C16 C15 C12 119.8(6) . . ?
C16 C15 C14 131.5(5) . . ?
C4 C7 C8 118.4(4) . . ?
C6 C7 C4 118.0(5) . . ?
C6 C7 C8 123.6(4) . . ?
C12 C13 H13 120.8 . . ?
C12 C13 C18 118.5(7) . . ?
C18 C13 H13 120.8 . . ?
C5 C6 Br1 115.3(4) . . ?
C7 C6 Br1 122.1(4) . . ?
C7 C6 C5 122.4(5) . . ?
C10 C9 C8 174.9(6) . . ?
C15 C16 H16 120.8 . . ?
C15 C16 C17 118.4(7) . . ?
C17 C16 H16 120.8 . . ?
C7 C8 H8 107.3 . . ?
C7 C8 C14 111.4(4) . . ?
C9 C8 C7 110.0(4) . . ?
C9 C8 H8 107.3 . . ?
C9 C8 C14 113.1(4) . . ?
C14 C8 H8 107.3 . . ?
C11 C14 C8 105.2(4) . . ?
C15 C14 C11 102.5(4) . . ?
C15 C14 C8 114.1(4) . . ?
C15 C14 C19 115.0(5) . . ?
C19 C14 C11 109.7(5) . . ?
C19 C14 C8 109.6(5) . . ?
C16 C17 H17 119.3 . . ?
C18 C17 C16 121.5(7) . . ?
C18 C17 H17 119.3 . . ?
O2 C1 O1 106.8(5) . . ?
O2 C1 H1A 110.4 . . ?
O2 C1 H1B 110.4 . . ?
O1 C1 H1A 110.4 . . ?
O1 C1 H1B 110.4 . . ?
H1A C1 H1B 108.6 . . ?
C19 O4 C20 118.7(8) . . ?
O3 C19 C14 124.5(6) . . ?
O3 C19 O4 125.4(6) . . ?
O4 C19 C14 110.1(6) . . ?
C9 C10 H10 180.0 . . ?
C13 C18 H18 119.8 . . ?
C17 C18 C13 120.4(7) . . ?
C17 C18 H18 119.8 . . ?
N1 C22 H22A 109.5 . . ?
N1 C22 H22B 109.5 . . ?
N1 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O4 C20 H20A 114.8 . . ?
O4 C20 H20B 114.8 . . ?
H20A C20 H20B 111.9 . . ?
C21 C20 O4 82.7(11) . . ?
C21 C20 H20A 114.8 . . ?
C21 C20 H20B 114.8 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 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
O2 C2 C3 O1 -0.2(7) . . . . ?
O2 C2 C3 C5 177.8(6) . . . . ?
O2 C2 C4 C7 179.2(6) . . . . ?
O5 C11 C14 C15 -171.8(5) . . . . ?
O5 C11 C14 C8 68.6(7) . . . . ?
O5 C11 C14 C19 -49.2(7) . . . . ?
N1 C11 C14 C15 11.4(5) . . . . ?
N1 C11 C14 C8 -108.2(5) . . . . ?
N1 C11 C14 C19 134.0(5) . . . . ?
N1 C12 C15 C16 -179.3(5) . . . . ?
N1 C12 C15 C14 6.9(6) . . . . ?
N1 C12 C13 C18 -179.2(6) . . . . ?
O1 C3 C5 C6 -179.3(6) . . . . ?
C11 N1 C12 C15 0.9(6) . . . . ?
C11 N1 C12 C13 -177.6(6) . . . . ?
C11 C14 C19 O3 98.8(9) . . . . ?
C11 C14 C19 O4 -81.7(7) . . . . ?
C2 O2 C1 O1 -0.2(8) . . . . ?
C2 C3 C5 C6 3.0(9) . . . . ?
C2 C4 C7 C6 3.0(9) . . . . ?
C2 C4 C7 C8 -177.8(5) . . . . ?
C3 O1 C1 O2 0.1(8) . . . . ?
C3 C2 C4 C7 -1.6(9) . . . . ?
C3 C5 C6 Br1 -176.9(4) . . . . ?
C3 C5 C6 C7 -1.5(10) . . . . ?
C4 C2 C3 O1 -179.5(6) . . . . ?
C4 C2 C3 C5 -1.5(9) . . . . ?
C4 C7 C6 Br1 173.6(5) . . . . ?
C4 C7 C6 C5 -1.4(10) . . . . ?
C4 C7 C8 C9 -54.3(7) . . . . ?
C4 C7 C8 C14 71.9(7) . . . . ?
C12 N1 C11 O5 175.2(5) . . . . ?
C12 N1 C11 C14 -8.0(6) . . . . ?
C12 C15 C16 C17 0.5(9) . . . . ?
C12 C15 C14 C11 -11.0(5) . . . . ?
C12 C15 C14 C8 102.2(5) . . . . ?
C12 C15 C14 C19 -129.9(5) . . . . ?
C12 C13 C18 C17 -4.2(10) . . . . ?
C15 C12 C13 C18 2.5(9) . . . . ?
C15 C16 C17 C18 -2.2(11) . . . . ?
C15 C14 C19 O3 -146.4(7) . . . . ?
C15 C14 C19 O4 33.2(8) . . . . ?
C7 C8 C14 C11 48.8(5) . . . . ?
C7 C8 C14 C15 -62.7(6) . . . . ?
C7 C8 C14 C19 166.8(5) . . . . ?
C13 C12 C15 C16 -0.7(8) . . . . ?
C13 C12 C15 C14 -174.5(5) . . . . ?
C6 C7 C8 C9 124.9(6) . . . . ?
C6 C7 C8 C14 -108.8(7) . . . . ?
C9 C8 C14 C11 173.3(4) . . . . ?
C9 C8 C14 C15 61.8(6) . . . . ?
C9 C8 C14 C19 -68.7(6) . . . . ?
C16 C15 C14 C11 176.2(6) . . . . ?
C16 C15 C14 C8 -70.6(7) . . . . ?
C16 C15 C14 C19 57.3(8) . . . . ?
C16 C17 C18 C13 4.1(11) . . . . ?
C8 C7 C6 Br1 -5.6(9) . . . . ?
C8 C7 C6 C5 179.4(6) . . . . ?
C8 C14 C19 O3 -16.3(9) . . . . ?
C8 C14 C19 O4 163.2(6) . . . . ?
C14 C15 C16 C17 172.6(6) . . . . ?
C1 O2 C2 C3 0.3(7) . . . . ?
C1 O2 C2 C4 179.6(6) . . . . ?
C1 O1 C3 C2 0.0(7) . . . . ?
C1 O1 C3 C5 -177.8(7) . . . . ?
C19 O4 C20 C21 102.1(12) . . . . ?
C22 N1 C11 O5 -14.5(9) . . . . ?
C22 N1 C11 C14 162.3(5) . . . . ?
C22 N1 C12 C15 -169.5(5) . . . . ?
C22 N1 C12 C13 12.1(9) . . . . ?
C20 O4 C19 O3 -16.5(14) . . . . ?
C20 O4 C19 C14 163.9(8) . . . . ?

_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_ycs20220325chen2_0m
_database_code_depnum_ccdc_archive 'CCDC 2181912'
loop_
_audit_author_name
_audit_author_address
'Kai zhangkai'
;Jiangsu Normal University
China
;
_audit_update_record             
;
2022-06-26 deposited with the CCDC.	2022-09-12 downloaded from the CCDC.
;
_audit_creation_date             2022-06-25
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        zk-2
_chemical_formula_moiety         'C21 H18 Br N O3'
_chemical_formula_sum            'C21 H18 Br N O3'
_chemical_formula_weight         412.27
_chemical_absolute_configuration rm
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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                   8.888(3)
_cell_length_b                   13.957(4)
_cell_length_c                   15.546(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1928.3(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3718
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      21.727
_cell_measurement_theta_min      2.620
_shelx_estimated_absorpt_T_max   0.673
_shelx_estimated_absorpt_T_min   0.673
_exptl_absorpt_coefficient_mu    2.151
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.4700
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/3 (Bruker,2014/3) was used for absorption correction.
wR2(int) was 0.1221 before and 0.0648 after correction.
The Ratio of minimum to maximum transmission is 0.6306.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.420
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_av_unetI/netI     0.0609
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            10699
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.150
_diffrn_reflns_theta_min         2.620
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.741
_reflns_Friedel_fraction_full    0.991
_reflns_Friedel_fraction_max     0.988
_reflns_number_gt                2991
_reflns_number_total             3826
_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 v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.304
_refine_diff_density_min         -0.350
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 
;
 Flack x determined using 1043 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.004(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3826
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0545
_refine_ls_R_factor_gt           0.0371
_refine_ls_restrained_S_all      1.043
_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)+(0.0314P)²+0.1859P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0882
_refine_ls_wR_factor_ref         0.0948
_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. Restrained distances
 C2-C1
 1.54 with sigma of 0.02
 C1-C2
 1.54 with sigma of 0.02
3. Rigid bond restraints
 C1, C2
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
4.a Ternary CH refined with riding coordinates:
 C5(H5)
4.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
4.c Aromatic/amide H refined with riding coordinates:
 C17(H17), C18(H18), C12(H12), C13(H13), C21(H21), C20(H20), C15(H15), C14(H14)
4.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C1(H1A,H1B,H1C)
4.e :
 C7(H7)
;
_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
Br1 Br 0.37520(7) 0.27141(4) 0.48814(4) 0.0896(3) Uani 1 1 d . . . . .
O1 O 0.8780(4) 0.6006(2) 0.24529(18) 0.0604(8) Uani 1 1 d . . . . .
O2 O 0.7410(4) 0.8504(2) 0.3763(2) 0.0688(9) Uani 1 1 d . . . . .
N1 N 0.6336(4) 0.5979(2) 0.20044(19) 0.0465(8) Uani 1 1 d . . . . .
C5 C 0.7061(4) 0.6527(3) 0.4148(2) 0.0413(9) Uani 1 1 d . . . . .
H5 H 0.661396 0.699410 0.454311 0.050 Uiso 1 1 calc R U . . .
O3 O 0.8072(5) 0.8121(2) 0.2429(2) 0.0975(15) Uani 1 1 d . . . . .
C4 C 0.6822(4) 0.6933(3) 0.3222(2) 0.0387(8) Uani 1 1 d . . . . .
C8 C 0.7481(5) 0.6261(3) 0.2525(2) 0.0410(9) Uani 1 1 d . . . . .
C16 C 0.6246(4) 0.5582(3) 0.4304(2) 0.0401(8) Uani 1 1 d . . . . .
C6 C 0.8670(5) 0.6461(3) 0.4378(2) 0.0469(9) Uani 1 1 d . . . . .
C3 C 0.7477(5) 0.7944(3) 0.3179(3) 0.0492(10) Uani 1 1 d . . . . .
C10 C 0.4961(5) 0.6385(3) 0.2257(3) 0.0460(10) Uani 1 1 d . . . . .
C17 C 0.6694(5) 0.4736(3) 0.3923(3) 0.0505(10) Uani 1 1 d . . . . .
H17 H 0.750641 0.474204 0.354536 0.061 Uiso 1 1 calc R U . . .
C18 C 0.5968(5) 0.3882(3) 0.4087(3) 0.0555(11) Uani 1 1 d . . . . .
H18 H 0.627922 0.331691 0.382454 0.067 Uiso 1 1 calc R U . . .
C19 C 0.4774(5) 0.3887(3) 0.4646(3) 0.0555(11) Uani 1 1 d . . . . .
C11 C 0.5181(4) 0.6971(3) 0.2975(2) 0.0395(9) Uani 1 1 d . . . . .
C7 C 0.9924(6) 0.6389(4) 0.4593(3) 0.0624(12) Uani 1 1 d . . . . .
H7 H 1.092306 0.633197 0.476389 0.075 Uiso 1 1 calc R U . . .
C12 C 0.3983(5) 0.7450(3) 0.3340(3) 0.0595(12) Uani 1 1 d . . . . .
H12 H 0.411952 0.784822 0.381301 0.071 Uiso 1 1 calc R U . . .
C13 C 0.2557(6) 0.7318(5) 0.2978(4) 0.0751(16) Uani 1 1 d . . . . .
H13 H 0.172784 0.762598 0.321617 0.090 Uiso 1 1 calc R U . . .
C21 C 0.5043(5) 0.5565(3) 0.4864(3) 0.0555(10) Uani 1 1 d . . . . .
H21 H 0.472628 0.612966 0.512416 0.067 Uiso 1 1 calc R U . . .
C20 C 0.4297(5) 0.4710(3) 0.5043(3) 0.0658(12) Uani 1 1 d . . . . .
H20 H 0.349090 0.469812 0.542389 0.079 Uiso 1 1 calc R U . . .
C15 C 0.3571(6) 0.6278(4) 0.1897(3) 0.0675(13) Uani 1 1 d . . . . .
H15 H 0.343606 0.590327 0.140811 0.081 Uiso 1 1 calc R U . . .
C14 C 0.2374(6) 0.6741(5) 0.2278(4) 0.0802(17) Uani 1 1 d . . . . .
H14 H 0.141451 0.665817 0.205085 0.096 Uiso 1 1 calc R U . . .
C9 C 0.6536(7) 0.5305(3) 0.1301(3) 0.0782(14) Uani 1 1 d . . . . .
H9A H 0.758903 0.517538 0.122573 0.117 Uiso 1 1 calc R U . . .
H9B H 0.613615 0.557583 0.078105 0.117 Uiso 1 1 calc R U . . .
H9C H 0.601694 0.471993 0.143052 0.117 Uiso 1 1 calc R U . . .
C2 C 0.8579(12) 0.9107(4) 0.2274(5) 0.150(4) Uani 1 1 d D U . . .
H2A H 0.774132 0.954413 0.235151 0.180 Uiso 1 1 calc R U . . .
H2B H 0.935141 0.927404 0.268885 0.180 Uiso 1 1 calc R U . . .
C1 C 0.9126(12) 0.9202(7) 0.1483(5) 0.187(5) Uani 1 1 d D U . . .
H1A H 0.863520 0.875411 0.110667 0.281 Uiso 1 1 calc R U . . .
H1B H 1.018772 0.907649 0.148791 0.281 Uiso 1 1 calc R U . . .
H1C H 0.894848 0.984215 0.128182 0.281 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
Br1 C19 1.907(4) . ?
O1 C8 1.214(5) . ?
O2 C3 1.199(5) . ?
N1 C8 1.358(5) . ?
N1 C10 1.403(5) . ?
N1 C9 1.454(5) . ?
C5 H5 0.9800 . ?
C5 C4 1.561(5) . ?
C5 C16 1.525(5) . ?
C5 C6 1.477(6) . ?
O3 C3 1.303(5) . ?
O3 C2 1.469(6) . ?
C4 C8 1.548(5) . ?
C4 C3 1.529(6) . ?
C4 C11 1.509(5) . ?
C16 C17 1.380(5) . ?
C16 C21 1.379(5) . ?
C6 C7 1.168(6) . ?
C10 C11 1.397(6) . ?
C10 C15 1.364(6) . ?
C17 H17 0.9300 . ?
C17 C18 1.380(5) . ?
C18 H18 0.9300 . ?
C18 C19 1.372(6) . ?
C19 C20 1.371(6) . ?
C11 C12 1.379(5) . ?
C7 H7 0.9300 . ?
C12 H12 0.9300 . ?
C12 C13 1.399(7) . ?
C13 H13 0.9300 . ?
C13 C14 1.363(9) . ?
C21 H21 0.9300 . ?
C21 C20 1.393(6) . ?
C20 H20 0.9300 . ?
C15 H15 0.9300 . ?
C15 C14 1.379(8) . ?
C14 H14 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C1 1.329(9) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 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 N1 C10 111.6(3) . . ?
C8 N1 C9 122.9(4) . . ?
C10 N1 C9 125.4(4) . . ?
C4 C5 H5 106.4 . . ?
C16 C5 H5 106.4 . . ?
C16 C5 C4 113.3(3) . . ?
C6 C5 H5 106.4 . . ?
C6 C5 C4 112.2(3) . . ?
C6 C5 C16 111.5(3) . . ?
C3 O3 C2 116.6(4) . . ?
C8 C4 C5 112.0(3) . . ?
C3 C4 C5 108.8(3) . . ?
C3 C4 C8 112.6(3) . . ?
C11 C4 C5 112.2(3) . . ?
C11 C4 C8 102.1(3) . . ?
C11 C4 C3 109.0(3) . . ?
O1 C8 N1 125.0(4) . . ?
O1 C8 C4 127.0(4) . . ?
N1 C8 C4 108.0(3) . . ?
C17 C16 C5 122.3(3) . . ?
C21 C16 C5 118.9(3) . . ?
C21 C16 C17 118.7(4) . . ?
C7 C6 C5 177.1(4) . . ?
O2 C3 O3 125.1(4) . . ?
O2 C3 C4 123.4(4) . . ?
O3 C3 C4 111.6(4) . . ?
C11 C10 N1 109.8(3) . . ?
C15 C10 N1 128.9(4) . . ?
C15 C10 C11 121.3(4) . . ?
C16 C17 H17 119.2 . . ?
C16 C17 C18 121.6(4) . . ?
C18 C17 H17 119.2 . . ?
C17 C18 H18 120.8 . . ?
C19 C18 C17 118.4(4) . . ?
C19 C18 H18 120.8 . . ?
C18 C19 Br1 119.0(3) . . ?
C20 C19 Br1 119.1(3) . . ?
C20 C19 C18 121.9(4) . . ?
C10 C11 C4 108.5(3) . . ?
C12 C11 C4 131.2(4) . . ?
C12 C11 C10 120.3(4) . . ?
C6 C7 H7 180.0 . . ?
C11 C12 H12 121.0 . . ?
C11 C12 C13 118.0(5) . . ?
C13 C12 H12 121.0 . . ?
C12 C13 H13 119.8 . . ?
C14 C13 C12 120.5(5) . . ?
C14 C13 H13 119.8 . . ?
C16 C21 H21 119.7 . . ?
C16 C21 C20 120.7(4) . . ?
C20 C21 H21 119.7 . . ?
C19 C20 C21 118.7(4) . . ?
C19 C20 H20 120.6 . . ?
C21 C20 H20 120.6 . . ?
C10 C15 H15 121.0 . . ?
C10 C15 C14 118.0(5) . . ?
C14 C15 H15 121.0 . . ?
C13 C14 C15 121.9(5) . . ?
C13 C14 H14 119.1 . . ?
C15 C14 H14 119.1 . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O3 C2 H2A 109.5 . . ?
O3 C2 H2B 109.5 . . ?
H2A C2 H2B 108.0 . . ?
C1 C2 O3 110.9(6) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 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
Br1 C19 C20 C21 -179.6(4) . . . . ?
N1 C10 C11 C4 -1.0(4) . . . . ?
N1 C10 C11 C12 179.9(3) . . . . ?
N1 C10 C15 C14 178.7(4) . . . . ?
C5 C4 C8 O1 -59.4(5) . . . . ?
C5 C4 C8 N1 119.2(3) . . . . ?
C5 C4 C3 O2 -36.8(6) . . . . ?
C5 C4 C3 O3 144.8(4) . . . . ?
C5 C4 C11 C10 -118.9(3) . . . . ?
C5 C4 C11 C12 60.1(5) . . . . ?
C5 C16 C17 C18 178.4(4) . . . . ?
C5 C16 C21 C20 -178.1(4) . . . . ?
C4 C5 C16 C17 70.5(5) . . . . ?
C4 C5 C16 C21 -111.2(4) . . . . ?
C4 C11 C12 C13 -177.9(4) . . . . ?
C8 N1 C10 C11 0.3(4) . . . . ?
C8 N1 C10 C15 179.7(4) . . . . ?
C8 C4 C3 O2 -161.6(4) . . . . ?
C8 C4 C3 O3 20.0(5) . . . . ?
C8 C4 C11 C10 1.2(4) . . . . ?
C8 C4 C11 C12 -179.9(4) . . . . ?
C16 C5 C4 C8 -63.4(4) . . . . ?
C16 C5 C4 C3 171.4(3) . . . . ?
C16 C5 C4 C11 50.7(4) . . . . ?
C16 C17 C18 C19 -0.1(7) . . . . ?
C16 C21 C20 C19 -0.6(7) . . . . ?
C6 C5 C4 C8 64.0(4) . . . . ?
C6 C5 C4 C3 -61.2(4) . . . . ?
C6 C5 C4 C11 178.1(3) . . . . ?
C6 C5 C16 C17 -57.3(5) . . . . ?
C6 C5 C16 C21 121.0(4) . . . . ?
C3 O3 C2 C1 -178.4(8) . . . . ?
C3 C4 C8 O1 63.6(5) . . . . ?
C3 C4 C8 N1 -117.7(3) . . . . ?
C3 C4 C11 C10 120.5(4) . . . . ?
C3 C4 C11 C12 -60.6(5) . . . . ?
C10 N1 C8 O1 179.2(4) . . . . ?
C10 N1 C8 C4 0.5(4) . . . . ?
C10 C11 C12 C13 0.9(6) . . . . ?
C10 C15 C14 C13 2.1(8) . . . . ?
C17 C16 C21 C20 0.2(6) . . . . ?
C17 C18 C19 Br1 180.0(3) . . . . ?
C17 C18 C19 C20 -0.2(7) . . . . ?
C18 C19 C20 C21 0.6(7) . . . . ?
C11 C4 C8 O1 -179.7(4) . . . . ?
C11 C4 C8 N1 -1.0(4) . . . . ?
C11 C4 C3 O2 85.8(5) . . . . ?
C11 C4 C3 O3 -92.5(4) . . . . ?
C11 C10 C15 C14 -2.0(7) . . . . ?
C11 C12 C13 C14 -0.8(7) . . . . ?
C12 C13 C14 C15 -0.7(9) . . . . ?
C21 C16 C17 C18 0.1(6) . . . . ?
C15 C10 C11 C4 179.6(4) . . . . ?
C15 C10 C11 C12 0.5(6) . . . . ?
C9 N1 C8 O1 1.7(6) . . . . ?
C9 N1 C8 C4 -177.0(4) . . . . ?
C9 N1 C10 C11 177.7(4) . . . . ?
C9 N1 C10 C15 -2.9(7) . . . . ?
C2 O3 C3 O2 -5.4(9) . . . . ?
C2 O3 C3 C4 173.0(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
