# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_mo_shenbin_20190812_1_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1971783'
loop_
_audit_author_name
_audit_author_address
'Bin Shen' 'Sichuan university'
_audit_update_record             
;
2019-12-13 deposited with the CCDC.	2020-03-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H18 Br Cl0 N O2'
_chemical_formula_weight         408.28

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'
Cl Cl 0.1484 0.1585 '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'

_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'

_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+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.8675(3)
_cell_length_b                   12.4208(7)
_cell_length_c                   24.4967(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1785.30(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    4334
_cell_measurement_theta_min      2.99
_cell_measurement_theta_max      24.71

_exptl_crystal_description       BLCOK
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.519
_exptl_crystal_F_000             832
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    2.319
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6577
_exptl_absorpt_correction_T_max  0.7451
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_special_details           
;
 The following wavelength and cell were deduced by SADABS from the
 direction cosines etc. They are given here for emergency use only:
 CELL 0.71073    5.866   12.424   24.505   90.030   90.007   89.990
;

_diffrn_ambient_temperature      300(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'BRUEKR D8 VENTURE PHOTON II'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9416
_diffrn_reflns_av_unetI/netI     0.0486
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.985
_diffrn_reflns_theta_max         24.727
_diffrn_reflns_theta_full        24.727
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_point_group_measured_fraction_full 0.977
_reflns_number_total             2964
_reflns_number_gt                2558
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.695
_reflns_Friedel_fraction_max     0.974
_reflns_Friedel_fraction_full    0.974

_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0220P)²+0.3218P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 950 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.002(5)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2964
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0374
_refine_ls_R_factor_gt           0.0300
_refine_ls_wR_factor_ref         0.0705
_refine_ls_wR_factor_gt          0.0660
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.000
_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 -0.03363(9) 0.37546(4) 0.38188(2) 0.0623(2) Uani 1 1 d . . . . .
N1 N 0.1083(5) 0.4073(2) 0.62710(12) 0.0327(7) Uani 1 1 d . . . . .
C1 C 0.7049(8) 0.7672(3) 0.55180(16) 0.0438(11) Uani 1 1 d . . . . .
H1 H 0.782737 0.808959 0.526372 0.053 Uiso 1 1 calc R U . . .
O1 O 0.4755(8) 0.6596(3) 0.74467(13) 0.0769(12) Uani 1 1 d . . . . .
O2 O -0.0109(5) 0.4670(2) 0.73831(11) 0.0417(7) Uani 1 1 d . . . . .
C2 C 0.4994(8) 0.8009(3) 0.57217(17) 0.0462(10) Uani 1 1 d . . . . .
H2 H 0.440596 0.867279 0.561609 0.055 Uiso 1 1 calc R U . . .
C3 C 0.3788(7) 0.7371(3) 0.60826(17) 0.0395(10) Uani 1 1 d . . . . .
H3 H 0.238131 0.760626 0.621104 0.047 Uiso 1 1 calc R U . . .
C5 C 0.6768(6) 0.6083(3) 0.60651(16) 0.0380(9) Uani 1 1 d . . . . .
H5 H 0.741884 0.544471 0.618809 0.046 Uiso 1 1 calc R U . . .
C4 C 0.7947(7) 0.6713(3) 0.56935(18) 0.0435(10) Uani 1 1 d . . . . .
H4 H 0.935328 0.648387 0.556235 0.052 Uiso 1 1 calc R U . . .
C6 C 0.4640(6) 0.6383(3) 0.62575(12) 0.0272(7) Uani 1 1 d . . . . .
C7 C 0.3282(6) 0.5696(3) 0.66443(15) 0.0302(8) Uani 1 1 d . . . . .
H7 H 0.170602 0.595566 0.663132 0.036 Uiso 1 1 calc R U . . .
C9 C 0.3763(7) 0.4731(3) 0.75315(16) 0.0413(10) Uani 1 1 d . . . . .
H9 H 0.505868 0.453790 0.776429 0.050 Uiso 1 1 calc R U . . .
C8 C 0.4064(7) 0.5783(4) 0.72336(17) 0.0425(11) Uani 1 1 d . . . . .
C10 C 0.3261(6) 0.3907(3) 0.70845(15) 0.0326(8) Uani 1 1 d . . . . .
H10 H 0.425911 0.327539 0.709605 0.039 Uiso 1 1 calc R U . . .
C11 C 0.3210(6) 0.4466(3) 0.65281(14) 0.0273(8) Uani 1 1 d . . . . .
H11 H 0.453384 0.425039 0.631010 0.033 Uiso 1 1 calc R U . . .
C12 C 0.1413(8) 0.4734(4) 0.78384(18) 0.0504(12) Uani 1 1 d . . . . .
H12 H 0.116506 0.535071 0.808064 0.060 Uiso 1 1 calc R U . . .
C13 C 0.1105(7) 0.3649(5) 0.81021(19) 0.0628(14) Uani 1 1 d . . . . .
H13 H 0.123448 0.348755 0.847157 0.075 Uiso 1 1 calc R U . . .
C14 C 0.0614(8) 0.2972(4) 0.7704(2) 0.0546(13) Uani 1 1 d . . . . .
H14 H 0.028108 0.224188 0.773302 0.065 Uiso 1 1 calc R U . . .
C15 C 0.0711(6) 0.3641(3) 0.71890(16) 0.0372(9) Uani 1 1 d . . . . .
C16 C -0.0249(7) 0.3391(3) 0.66381(15) 0.0380(9) Uani 1 1 d . . . . .
H16A H -0.005399 0.263588 0.654913 0.046 Uiso 1 1 calc R U . . .
H16B H -0.185609 0.357030 0.662025 0.046 Uiso 1 1 calc R U . . .
C17 C 0.0790(6) 0.4009(3) 0.57114(15) 0.0289(8) Uani 1 1 d . . . . .
C18 C -0.1131(7) 0.3491(3) 0.54949(17) 0.0389(10) Uani 1 1 d . . . . .
H18 H -0.218738 0.317828 0.572930 0.047 Uiso 1 1 calc R U . . .
C19 C -0.1478(7) 0.3441(3) 0.49354(17) 0.0406(10) Uani 1 1 d . . . . .
H19 H -0.277310 0.310742 0.479667 0.049 Uiso 1 1 calc R U . . .
C20 C 0.0090(7) 0.3882(3) 0.45883(15) 0.0409(9) Uani 1 1 d . . . . .
C21 C 0.2009(7) 0.4384(3) 0.47867(16) 0.0399(10) Uani 1 1 d . . . . .
H21 H 0.308037 0.466911 0.454716 0.048 Uiso 1 1 calc R U . . .
C22 C 0.2333(7) 0.4462(3) 0.53427(16) 0.0364(9) Uani 1 1 d . . . . .
H22 H 0.360564 0.482436 0.547516 0.044 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 C20 1.908(4) . ?
N1 C17 1.384(5) . ?
N1 C16 1.462(5) . ?
N1 C11 1.480(5) . ?
C1 C2 1.371(6) . ?
C1 C4 1.372(6) . ?
C1 H1 0.9300 . ?
O1 C8 1.206(5) . ?
O2 C12 1.431(5) . ?
O2 C15 1.446(5) . ?
C2 C3 1.382(6) . ?
C2 H2 0.9300 . ?
C3 C6 1.393(5) . ?
C3 H3 0.9300 . ?
C5 C4 1.385(6) . ?
C5 C6 1.386(5) . ?
C5 H5 0.9300 . ?
C4 H4 0.9300 . ?
C6 C7 1.504(5) . ?
C7 C8 1.519(6) . ?
C7 C11 1.554(5) . ?
C7 H7 0.9800 . ?
C9 C8 1.507(6) . ?
C9 C10 1.527(5) . ?
C9 C12 1.570(6) . ?
C9 H9 0.9800 . ?
C10 C11 1.530(5) . ?
C10 C15 1.553(5) . ?
C10 H10 0.9800 . ?
C11 H11 0.9800 . ?
C12 C13 1.506(7) . ?
C12 H12 0.9800 . ?
C13 C14 1.320(7) . ?
C13 H13 0.9300 . ?
C14 C15 1.511(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.495(5) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C22 1.398(5) . ?
C17 C18 1.402(5) . ?
C18 C19 1.387(6) . ?
C18 H18 0.9300 . ?
C19 C20 1.367(6) . ?
C19 H19 0.9300 . ?
C20 C21 1.375(6) . ?
C21 C22 1.379(6) . ?
C21 H21 0.9300 . ?
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
C17 N1 C16 120.6(3) . . ?
C17 N1 C11 123.1(3) . . ?
C16 N1 C11 112.3(3) . . ?
C2 C1 C4 119.3(4) . . ?
C2 C1 H1 120.4 . . ?
C4 C1 H1 120.4 . . ?
C12 O2 C15 95.6(3) . . ?
C1 C2 C3 120.6(4) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
C2 C3 C6 121.2(4) . . ?
C2 C3 H3 119.4 . . ?
C6 C3 H3 119.4 . . ?
C4 C5 C6 121.4(4) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C1 C4 C5 120.3(4) . . ?
C1 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C5 C6 C3 117.2(3) . . ?
C5 C6 C7 122.6(3) . . ?
C3 C6 C7 120.2(3) . . ?
C6 C7 C8 113.5(3) . . ?
C6 C7 C11 117.2(3) . . ?
C8 C7 C11 104.6(3) . . ?
C6 C7 H7 107.0 . . ?
C8 C7 H7 107.0 . . ?
C11 C7 H7 107.0 . . ?
C8 C9 C10 104.8(3) . . ?
C8 C9 C12 109.4(4) . . ?
C10 C9 C12 100.1(3) . . ?
C8 C9 H9 113.8 . . ?
C10 C9 H9 113.8 . . ?
C12 C9 H9 113.8 . . ?
O1 C8 C9 123.7(4) . . ?
O1 C8 C7 124.9(4) . . ?
C9 C8 C7 111.3(3) . . ?
C9 C10 C11 109.8(3) . . ?
C9 C10 C15 102.1(3) . . ?
C11 C10 C15 103.0(3) . . ?
C9 C10 H10 113.6 . . ?
C11 C10 H10 113.6 . . ?
C15 C10 H10 113.6 . . ?
N1 C11 C10 104.3(3) . . ?
N1 C11 C7 115.1(3) . . ?
C10 C11 C7 106.4(3) . . ?
N1 C11 H11 110.3 . . ?
C10 C11 H11 110.3 . . ?
C7 C11 H11 110.3 . . ?
O2 C12 C13 102.1(4) . . ?
O2 C12 C9 100.1(3) . . ?
C13 C12 C9 108.0(4) . . ?
O2 C12 H12 115.0 . . ?
C13 C12 H12 115.0 . . ?
C9 C12 H12 115.0 . . ?
C14 C13 C12 106.2(4) . . ?
C14 C13 H13 126.9 . . ?
C12 C13 H13 126.9 . . ?
C13 C14 C15 105.0(4) . . ?
C13 C14 H14 127.5 . . ?
C15 C14 H14 127.5 . . ?
O2 C15 C16 110.8(3) . . ?
O2 C15 C14 101.5(3) . . ?
C16 C15 C14 128.6(4) . . ?
O2 C15 C10 100.7(3) . . ?
C16 C15 C10 105.0(3) . . ?
C14 C15 C10 106.9(3) . . ?
N1 C16 C15 103.5(3) . . ?
N1 C16 H16A 111.1 . . ?
C15 C16 H16A 111.1 . . ?
N1 C16 H16B 111.1 . . ?
C15 C16 H16B 111.1 . . ?
H16A C16 H16B 109.0 . . ?
N1 C17 C22 122.4(3) . . ?
N1 C17 C18 120.1(3) . . ?
C22 C17 C18 117.5(3) . . ?
C19 C18 C17 120.8(4) . . ?
C19 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
C20 C19 C18 119.9(4) . . ?
C20 C19 H19 120.1 . . ?
C18 C19 H19 120.1 . . ?
C19 C20 C21 120.8(4) . . ?
C19 C20 Br1 119.5(3) . . ?
C21 C20 Br1 119.6(3) . . ?
C20 C21 C22 119.6(4) . . ?
C20 C21 H21 120.2 . . ?
C22 C21 H21 120.2 . . ?
C21 C22 C17 121.4(4) . . ?
C21 C22 H22 119.3 . . ?
C17 C22 H22 119.3 . . ?

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
C4 C1 C2 C3 -2.7(6) . . . . ?
C1 C2 C3 C6 1.3(6) . . . . ?
C2 C1 C4 C5 1.1(6) . . . . ?
C6 C5 C4 C1 1.8(6) . . . . ?
C4 C5 C6 C3 -3.1(5) . . . . ?
C4 C5 C6 C7 177.6(4) . . . . ?
C2 C3 C6 C5 1.6(5) . . . . ?
C2 C3 C6 C7 -179.1(4) . . . . ?
C5 C6 C7 C8 79.3(4) . . . . ?
C3 C6 C7 C8 -100.0(4) . . . . ?
C5 C6 C7 C11 -42.9(5) . . . . ?
C3 C6 C7 C11 137.8(4) . . . . ?
C10 C9 C8 O1 -170.6(5) . . . . ?
C12 C9 C8 O1 82.8(5) . . . . ?
C10 C9 C8 C7 12.1(4) . . . . ?
C12 C9 C8 C7 -94.5(4) . . . . ?
C6 C7 C8 O1 36.0(6) . . . . ?
C11 C7 C8 O1 164.9(5) . . . . ?
C6 C7 C8 C9 -146.8(3) . . . . ?
C11 C7 C8 C9 -17.8(4) . . . . ?
C8 C9 C10 C11 -1.2(4) . . . . ?
C12 C9 C10 C11 112.1(3) . . . . ?
C8 C9 C10 C15 -110.0(3) . . . . ?
C12 C9 C10 C15 3.4(4) . . . . ?
C17 N1 C11 C10 -153.1(3) . . . . ?
C16 N1 C11 C10 4.4(4) . . . . ?
C17 N1 C11 C7 90.8(4) . . . . ?
C16 N1 C11 C7 -111.7(3) . . . . ?
C9 C10 C11 N1 -131.6(3) . . . . ?
C15 C10 C11 N1 -23.4(4) . . . . ?
C9 C10 C11 C7 -9.5(4) . . . . ?
C15 C10 C11 C7 98.7(3) . . . . ?
C6 C7 C11 N1 -102.3(4) . . . . ?
C8 C7 C11 N1 131.1(3) . . . . ?
C6 C7 C11 C10 142.8(3) . . . . ?
C8 C7 C11 C10 16.1(4) . . . . ?
C15 O2 C12 C13 -49.6(3) . . . . ?
C15 O2 C12 C9 61.4(3) . . . . ?
C8 C9 C12 O2 70.2(4) . . . . ?
C10 C9 C12 O2 -39.6(4) . . . . ?
C8 C9 C12 C13 176.6(4) . . . . ?
C10 C9 C12 C13 66.8(4) . . . . ?
O2 C12 C13 C14 30.8(5) . . . . ?
C9 C12 C13 C14 -74.1(5) . . . . ?
C12 C13 C14 C15 2.1(5) . . . . ?
C12 O2 C15 C16 -169.8(3) . . . . ?
C12 O2 C15 C14 50.9(3) . . . . ?
C12 O2 C15 C10 -59.1(3) . . . . ?
C13 C14 C15 O2 -34.0(4) . . . . ?
C13 C14 C15 C16 -162.8(4) . . . . ?
C13 C14 C15 C10 71.1(5) . . . . ?
C9 C10 C15 O2 33.3(3) . . . . ?
C11 C10 C15 O2 -80.6(3) . . . . ?
C9 C10 C15 C16 148.4(3) . . . . ?
C11 C10 C15 C16 34.5(4) . . . . ?
C9 C10 C15 C14 -72.4(4) . . . . ?
C11 C10 C15 C14 173.7(3) . . . . ?
C17 N1 C16 C15 175.4(3) . . . . ?
C11 N1 C16 C15 17.3(4) . . . . ?
O2 C15 C16 N1 76.3(4) . . . . ?
C14 C15 C16 N1 -158.4(4) . . . . ?
C10 C15 C16 N1 -31.6(4) . . . . ?
C16 N1 C17 C22 -165.9(3) . . . . ?
C11 N1 C17 C22 -10.2(5) . . . . ?
C16 N1 C17 C18 15.3(5) . . . . ?
C11 N1 C17 C18 171.0(3) . . . . ?
N1 C17 C18 C19 178.5(3) . . . . ?
C22 C17 C18 C19 -0.3(5) . . . . ?
C17 C18 C19 C20 1.2(6) . . . . ?
C18 C19 C20 C21 -0.4(6) . . . . ?
C18 C19 C20 Br1 177.3(3) . . . . ?
C19 C20 C21 C22 -1.3(6) . . . . ?
Br1 C20 C21 C22 -179.1(3) . . . . ?
C20 C21 C22 C17 2.2(6) . . . . ?
N1 C17 C22 C21 179.8(4) . . . . ?
C18 C17 C22 C21 -1.4(6) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C10 H10 O1 0.98 2.44 3.305(5) 147.2 3_646

_refine_diff_density_max         0.489
_refine_diff_density_min         -0.522
_refine_diff_density_rms         0.041

