# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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. 
# 
#######################################################################

data_201907185
_database_code_depnum_ccdc_archive 'CCDC 1956109'
loop_
_audit_author_name
_audit_author_address
'shi yaqi'
;Zhengzhou University
China
;
_audit_update_record             
;
2019-09-26 deposited with the CCDC.	2020-06-01 downloaded from the CCDC.
;
_audit_creation_date             2019-07-11
_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 H17 Br N2 O3'
_chemical_formula_sum            'C20 H17 Br N2 O3'
_chemical_formula_weight         413.26
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H20O6N4K1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   16.6385(13)
_cell_length_b                   14.3268(8)
_cell_length_c                   7.7041(5)
_cell_angle_alpha                90
_cell_angle_beta                 100.731(7)
_cell_angle_gamma                90
_cell_volume                     1804.3(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1643
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      68.5280
_cell_measurement_theta_min      6.1570
_shelx_estimated_absorpt_T_max   0.713
_shelx_estimated_absorpt_T_min   0.573
_exptl_absorpt_coefficient_mu    3.296
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92381
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.521
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0468
_diffrn_reflns_av_unetI/netI     0.0652
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            6920
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.080
_diffrn_reflns_theta_max         67.080
_diffrn_reflns_theta_min         4.103
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -55.00   38.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000    0.0000   90.0000 93

#__ type_ start__ end____ width___ exp.time_
  2 omega  -92.00  -66.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000    0.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
  3 omega  -18.00   17.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   37.0000  120.0000 35

#__ type_ start__ end____ width___ exp.time_
  4 omega   -4.00   66.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000 -180.0000 70

#__ type_ start__ end____ width___ exp.time_
  5 omega   67.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000 -180.0000 42

#__ type_ start__ end____ width___ exp.time_
  6 omega   27.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
  7 omega   72.00   98.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
  8 omega   80.00  106.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000  -60.0000 26

#__ type_ start__ end____ width___ exp.time_
  9 omega   63.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000  -30.0000 27

#__ type_ start__ end____ width___ exp.time_
 10 omega  127.00  157.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000    0.0000 30

#__ type_ start__ end____ width___ exp.time_
 11 omega   93.00  172.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -120.0000 79

#__ type_ start__ end____ width___ exp.time_
 12 omega   50.00  120.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000 -150.0000 70

#__ type_ start__ end____ width___ exp.time_
 13 omega   42.00   81.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000    0.0000 39

#__ type_ start__ end____ width___ exp.time_
 14 omega   42.00  100.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -180.0000 58

#__ type_ start__ end____ width___ exp.time_
 15 omega   65.00  176.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000 -180.0000 111

#__ type_ start__ end____ width___ exp.time_
 16 omega   48.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  150.0000 42

#__ type_ start__ end____ width___ exp.time_
 17 omega   57.00  112.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   90.0000 55

#__ type_ start__ end____ width___ exp.time_
 18 omega   42.00   96.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000    0.0000 54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0138872000
_diffrn_orient_matrix_UB_12      -0.0997878000
_diffrn_orient_matrix_UB_13      0.0739803000
_diffrn_orient_matrix_UB_21      -0.0050023000
_diffrn_orient_matrix_UB_22      0.0363085000
_diffrn_orient_matrix_UB_23      0.1857714000
_diffrn_orient_matrix_UB_31      -0.0931387000
_diffrn_orient_matrix_UB_32      -0.0168803000
_diffrn_orient_matrix_UB_33      -0.0372066000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2250
_reflns_number_total             3221
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.353
_refine_diff_density_min         -0.433
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       0.0037(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     242
_refine_ls_number_reflns         3221
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0755
_refine_ls_R_factor_gt           0.0486
_refine_ls_restrained_S_all      1.053
_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)+(0.0455P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1062
_refine_ls_wR_factor_ref         0.1265
_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:
 C18(H18)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C7(H7), C8(H8), C9(H9), C13(H13), C14(H14), C15(H15), C16(H16)
2.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C20(H20A,H20B,H20C)
;
_atom_sites_solution_hydrogens   mixed
_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
Br1 Br 0.39023(4) 0.94226(4) 0.36865(7) 0.0704(3) Uani 1 1 d . . . . .
C1 C 0.3359(3) 0.8294(3) 0.4076(5) 0.0454(10) Uani 1 1 d . . . . .
C2 C 0.2605(3) 0.8358(3) 0.4507(5) 0.0477(10) Uani 1 1 d . . . . .
H2 H 0.2381 0.8939 0.4672 0.057 Uiso 1 1 calc R . . . .
C3 C 0.2173(2) 0.7549(3) 0.4696(5) 0.0466(10) Uani 1 1 d . . . . .
H3 H 0.1664 0.7593 0.5027 0.056 Uiso 1 1 calc R . . . .
C4 C 0.2475(2) 0.6690(3) 0.4411(5) 0.0388(9) Uani 1 1 d . . . . .
C5 C 0.3276(2) 0.6598(3) 0.4000(4) 0.0360(8) Uani 1 1 d . . . . .
C6 C 0.3736(2) 0.7429(3) 0.3868(5) 0.0406(9) Uani 1 1 d . . . . .
C7 C 0.4544(2) 0.7348(3) 0.3537(6) 0.0537(11) Uani 1 1 d . . . . .
H7 H 0.4849 0.7886 0.3461 0.064 Uiso 1 1 calc R . . . .
C8 C 0.4880(2) 0.6506(4) 0.3330(6) 0.0600(13) Uani 1 1 d . . . . .
H8 H 0.5416 0.6469 0.3149 0.072 Uiso 1 1 calc R . . . .
C9 C 0.4426(3) 0.5687(3) 0.3386(6) 0.0537(11) Uani 1 1 d . . . . .
H9 H 0.4659 0.5114 0.3204 0.064 Uiso 1 1 calc R . . . .
C10 C 0.3638(2) 0.5718(3) 0.3707(5) 0.0406(9) Uani 1 1 d . . . . .
C11 C 0.1277(2) 0.5733(3) 0.3374(5) 0.0439(10) Uani 1 1 d . . . . .
C12 C 0.0849(2) 0.4840(3) 0.3678(5) 0.0438(10) Uani 1 1 d . . . . .
C13 C 0.0151(3) 0.4585(3) 0.2533(6) 0.0621(13) Uani 1 1 d . . . . .
H13 H -0.0076 0.4971 0.1599 0.075 Uiso 1 1 calc R . . . .
C14 C -0.0209(3) 0.3734(4) 0.2807(8) 0.0765(16) Uani 1 1 d . . . . .
H14 H -0.0680 0.3538 0.2046 0.092 Uiso 1 1 calc R . . . .
C15 C 0.0135(3) 0.3193(4) 0.4198(8) 0.0718(15) Uani 1 1 d . . . . .
H15 H -0.0090 0.2619 0.4403 0.086 Uiso 1 1 calc R . . . .
C16 C 0.0822(3) 0.3520(3) 0.5289(7) 0.0653(13) Uani 1 1 d . . . . .
H16 H 0.1045 0.3156 0.6259 0.078 Uiso 1 1 calc R . . . .
C17 C 0.3211(2) 0.4798(3) 0.3626(5) 0.0440(9) Uani 1 1 d . . . . .
C18 C 0.2496(3) 0.3688(3) 0.1575(7) 0.0624(13) Uani 1 1 d . . . . .
H18 H 0.2216 0.3486 0.2522 0.075 Uiso 1 1 calc R . . . .
C19 C 0.3177(4) 0.3025(4) 0.1441(9) 0.097(2) Uani 1 1 d . . . . .
H19A H 0.3444 0.3217 0.0499 0.145 Uiso 1 1 calc GR . . . .
H19B H 0.2958 0.2408 0.1204 0.145 Uiso 1 1 calc GR . . . .
H19C H 0.3564 0.3024 0.2534 0.145 Uiso 1 1 calc GR . . . .
C20 C 0.1886(4) 0.3809(4) -0.0095(7) 0.0949(19) Uani 1 1 d . . . . .
H20A H 0.1497 0.4280 0.0072 0.142 Uiso 1 1 calc GR . . . .
H20B H 0.1607 0.3229 -0.0404 0.142 Uiso 1 1 calc GR . . . .
H20C H 0.2163 0.3996 -0.1026 0.142 Uiso 1 1 calc GR . . . .
N1 N 0.1983(2) 0.5887(2) 0.4523(5) 0.0420(8) Uani 1 1 d . . . . .
H1 H 0.214(3) 0.551(3) 0.526(6) 0.051(14) Uiso 1 1 d . . . . .
N2 N 0.1193(2) 0.4314(2) 0.5063(5) 0.0533(9) Uani 1 1 d . . . . .
O1 O 0.09949(19) 0.6252(2) 0.2158(4) 0.0691(10) Uani 1 1 d . . . . .
O2 O 0.3244(2) 0.4270(2) 0.4844(4) 0.0635(9) Uani 1 1 d . . . . .
O3 O 0.28413(18) 0.46199(19) 0.1977(4) 0.0527(8) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C1 1.904(4) . ?
C1 C2 1.359(5) . ?
C1 C6 1.411(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.386(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.362(5) . ?
C4 C5 1.433(5) . ?
C4 N1 1.423(5) . ?
C5 C6 1.430(5) . ?
C5 C10 1.432(5) . ?
C6 C7 1.419(5) . ?
C7 H7 0.9300 . ?
C7 C8 1.352(6) . ?
C8 H8 0.9300 . ?
C8 C9 1.400(6) . ?
C9 H9 0.9300 . ?
C9 C10 1.378(5) . ?
C10 C17 1.494(5) . ?
C11 C12 1.504(5) . ?
C11 N1 1.351(5) . ?
C11 O1 1.220(5) . ?
C12 C13 1.371(6) . ?
C12 N2 1.344(5) . ?
C13 H13 0.9300 . ?
C13 C14 1.391(7) . ?
C14 H14 0.9300 . ?
C14 C15 1.360(7) . ?
C15 H15 0.9300 . ?
C15 C16 1.369(6) . ?
C16 H16 0.9300 . ?
C16 N2 1.321(5) . ?
C17 O2 1.198(5) . ?
C17 O3 1.330(5) . ?
C18 H18 0.9800 . ?
C18 C19 1.496(6) . ?
C18 C20 1.493(7) . ?
C18 O3 1.464(5) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
N1 H1 0.79(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 Br1 117.9(3) . . ?
C2 C1 C6 122.5(4) . . ?
C6 C1 Br1 119.5(3) . . ?
C1 C2 H2 120.3 . . ?
C1 C2 C3 119.3(4) . . ?
C3 C2 H2 120.4 . . ?
C2 C3 H3 119.2 . . ?
C4 C3 C2 121.6(4) . . ?
C4 C3 H3 119.2 . . ?
C3 C4 C5 120.4(4) . . ?
C3 C4 N1 119.1(3) . . ?
N1 C4 C5 120.5(3) . . ?
C6 C5 C4 118.1(3) . . ?
C6 C5 C10 118.4(3) . . ?
C10 C5 C4 123.5(3) . . ?
C1 C6 C5 117.9(3) . . ?
C1 C6 C7 123.3(4) . . ?
C7 C6 C5 118.8(4) . . ?
C6 C7 H7 119.3 . . ?
C8 C7 C6 121.4(4) . . ?
C8 C7 H7 119.3 . . ?
C7 C8 H8 119.8 . . ?
C7 C8 C9 120.4(4) . . ?
C9 C8 H8 119.8 . . ?
C8 C9 H9 119.5 . . ?
C10 C9 C8 121.0(4) . . ?
C10 C9 H9 119.5 . . ?
C5 C10 C17 124.9(3) . . ?
C9 C10 C5 119.9(4) . . ?
C9 C10 C17 115.1(4) . . ?
N1 C11 C12 114.6(4) . . ?
O1 C11 C12 120.8(4) . . ?
O1 C11 N1 124.5(4) . . ?
C13 C12 C11 119.7(4) . . ?
N2 C12 C11 117.2(4) . . ?
N2 C12 C13 123.1(4) . . ?
C12 C13 H13 120.9 . . ?
C12 C13 C14 118.2(5) . . ?
C14 C13 H13 120.9 . . ?
C13 C14 H14 120.4 . . ?
C15 C14 C13 119.3(5) . . ?
C15 C14 H14 120.4 . . ?
C14 C15 H15 121.0 . . ?
C14 C15 C16 118.0(5) . . ?
C16 C15 H15 121.0 . . ?
C15 C16 H16 117.6 . . ?
N2 C16 C15 124.8(5) . . ?
N2 C16 H16 117.6 . . ?
O2 C17 C10 125.0(4) . . ?
O2 C17 O3 124.9(4) . . ?
O3 C17 C10 109.9(3) . . ?
C19 C18 H18 109.5 . . ?
C20 C18 H18 109.5 . . ?
C20 C18 C19 114.6(5) . . ?
O3 C18 H18 109.5 . . ?
O3 C18 C19 108.8(4) . . ?
O3 C18 C20 104.7(4) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C4 N1 H1 118(3) . . ?
C11 N1 C4 122.1(3) . . ?
C11 N1 H1 119(3) . . ?
C16 N2 C12 116.6(4) . . ?
C17 O3 C18 118.1(3) . . ?

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
N1 H1 O2 0.79(4) 2.61(4) 3.104(5) 122(4) .

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 176.2(3) . . . . ?
Br1 C1 C6 C5 -173.9(3) . . . . ?
Br1 C1 C6 C7 6.1(5) . . . . ?
C1 C2 C3 C4 -2.0(6) . . . . ?
C1 C6 C7 C8 -179.4(4) . . . . ?
C2 C1 C6 C5 4.4(6) . . . . ?
C2 C1 C6 C7 -175.6(4) . . . . ?
C2 C3 C4 C5 3.6(6) . . . . ?
C2 C3 C4 N1 -176.3(4) . . . . ?
C3 C4 C5 C6 -1.2(5) . . . . ?
C3 C4 C5 C10 179.1(4) . . . . ?
C3 C4 N1 C11 65.5(5) . . . . ?
C4 C5 C6 C1 -2.6(5) . . . . ?
C4 C5 C6 C7 177.3(3) . . . . ?
C4 C5 C10 C9 -177.5(4) . . . . ?
C4 C5 C10 C17 5.8(6) . . . . ?
C5 C4 N1 C11 -114.4(4) . . . . ?
C5 C6 C7 C8 0.6(6) . . . . ?
C5 C10 C17 O2 -95.4(5) . . . . ?
C5 C10 C17 O3 89.4(4) . . . . ?
C6 C1 C2 C3 -2.1(6) . . . . ?
C6 C5 C10 C9 2.9(5) . . . . ?
C6 C5 C10 C17 -173.9(3) . . . . ?
C6 C7 C8 C9 1.9(7) . . . . ?
C7 C8 C9 C10 -2.0(7) . . . . ?
C8 C9 C10 C5 -0.4(6) . . . . ?
C8 C9 C10 C17 176.7(4) . . . . ?
C9 C10 C17 O2 87.7(5) . . . . ?
C9 C10 C17 O3 -87.6(4) . . . . ?
C10 C5 C6 C1 177.0(3) . . . . ?
C10 C5 C6 C7 -3.0(5) . . . . ?
C10 C17 O3 C18 170.7(3) . . . . ?
C11 C12 C13 C14 177.1(4) . . . . ?
C11 C12 N2 C16 -178.3(4) . . . . ?
C12 C11 N1 C4 178.9(3) . . . . ?
C12 C13 C14 C15 0.7(7) . . . . ?
C13 C12 N2 C16 -0.1(6) . . . . ?
C13 C14 C15 C16 0.7(8) . . . . ?
C14 C15 C16 N2 -2.0(8) . . . . ?
C15 C16 N2 C12 1.7(7) . . . . ?
C19 C18 O3 C17 -77.2(5) . . . . ?
C20 C18 O3 C17 159.9(4) . . . . ?
N1 C4 C5 C6 178.7(3) . . . . ?
N1 C4 C5 C10 -0.9(5) . . . . ?
N1 C11 C12 C13 -176.3(4) . . . . ?
N1 C11 C12 N2 1.9(5) . . . . ?
N2 C12 C13 C14 -1.0(7) . . . . ?
O1 C11 C12 C13 2.8(6) . . . . ?
O1 C11 C12 N2 -179.0(4) . . . . ?
O1 C11 N1 C4 -0.2(7) . . . . ?
O2 C17 O3 C18 -4.6(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
