# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_20210508-sgf-ww-22-1
_database_code_depnum_ccdc_archive 'CCDC 2114483'
loop_
_audit_author_name
_audit_author_address
'Dong-Liang Mo'
;Guangxi Normal University
China
;
_audit_update_record             
;
2021-10-07 deposited with the CCDC.	2022-01-31 downloaded from the CCDC.
;
_audit_creation_date             2021-05-10
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.06.28 svn.raecde09e for OlexSys, GUI svn.r6132)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H14 Br N3 O'
_chemical_formula_sum            'C20 H14 Br N3 O'
_chemical_formula_weight         392.25
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C152 H104 Br8 N32 O8 '
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      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   19.5352(5)
_cell_length_b                   14.0585(4)
_cell_length_c                   13.9778(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3838.8(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6642
_cell_measurement_temperature    295.48(10)
_cell_measurement_theta_max      62.5200
_cell_measurement_theta_min      3.1340
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.007
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53377
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'metallic light colourless'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1584
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0514
_diffrn_reflns_av_unetI/netI     0.0317
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            10503
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        62.679
_diffrn_reflns_theta_max         62.679
_diffrn_reflns_theta_min         3.874
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      295.48(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -11.00  16.00   0.50    0.40    --    0.62  37.00 -30.00   54
  2  ω    -40.00  -3.00   0.50    0.40    --    0.62 112.00-164.68   74
  3  ω     24.00  78.00   0.50    0.40    --    0.62  37.00 -30.00  108
  4  ω    126.00 156.00   0.50    2.00    --   83.03  81.00  69.00   60
  5  ω     99.00 157.00   0.50    2.00    --   83.03 125.00  90.00  116
  6  ω    -76.00 -50.00   0.50    2.00    --  -81.78 125.00 -60.00   52
  7  ω    -46.00 -20.00   0.50    2.00    --  -81.78  42.00-117.00   52
  8  ω    -42.00  -4.00   0.50    2.00    --  -81.78  37.00 -90.00   76
  9  ω    -27.00  -2.00   0.50    2.00    --  -81.78  19.00   0.00   50
 10  ω     11.00  38.00   0.50    2.00    --   83.03 -37.00   0.00   54
 11  ω     10.00  39.00   0.50    2.00    --   83.03 -37.00 150.00   58
 12  ω   -158.00 -69.00   0.50    2.00    --  -81.78 -42.00  90.00  178
 13  ω   -134.00 -82.00   0.50    2.00    --  -81.78-114.00-132.00  104
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0039465000
_diffrn_orient_matrix_UB_12      -0.0936074000
_diffrn_orient_matrix_UB_13      0.0571180000
_diffrn_orient_matrix_UB_21      0.0776362000
_diffrn_orient_matrix_UB_22      -0.0141260000
_diffrn_orient_matrix_UB_23      -0.0137890000
_diffrn_orient_matrix_UB_31      0.0134437000
_diffrn_orient_matrix_UB_32      0.0552187000
_diffrn_orient_matrix_UB_33      0.0931831000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2592
_reflns_number_total             3012
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     58.86
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.385
_refine_diff_density_min         -0.487
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.123
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3012
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0659
_refine_ls_R_factor_gt           0.0606
_refine_ls_restrained_S_all      1.123
_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)+(0.0631P)²+5.6653P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1691
_refine_ls_wR_factor_ref         0.1719
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C15(H15), C17(H17), C18(H18)
2.c X=CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
;
_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 0.61115(4) 0.68279(6) 0.42064(5) 0.1146(4) Uani 1 1 d . . . . .
O1 O 0.51202(18) 0.3198(3) 0.3717(3) 0.0828(10) Uani 1 1 d . . . . .
N1 N 0.1729(2) 0.3825(3) 0.2863(3) 0.0713(11) Uani 1 1 d . . . . .
N2 N 0.40222(18) 0.3400(3) 0.3239(3) 0.0588(9) Uani 1 1 d . . . . .
N3 N 0.34638(18) 0.4885(3) 0.3113(3) 0.0588(9) Uani 1 1 d . . . . .
C1 C 0.1920(2) 0.3973(3) 0.1882(4) 0.0657(12) Uani 1 1 d . . . . .
C2 C 0.1509(3) 0.4304(4) 0.1169(5) 0.0903(18) Uani 1 1 d . . . . .
H2 H 0.105310 0.446635 0.127279 0.108 Uiso 1 1 calc R U . . .
C3 C 0.1820(4) 0.4384(4) 0.0261(5) 0.101(2) Uani 1 1 d . . . . .
H3 H 0.155858 0.459860 -0.025194 0.121 Uiso 1 1 calc R U . . .
C4 C 0.2480(4) 0.4160(4) 0.0110(4) 0.0921(17) Uani 1 1 d . . . . .
H4 H 0.266496 0.423558 -0.049869 0.110 Uiso 1 1 calc R U . . .
C5 C 0.2897(3) 0.3814(3) 0.0853(4) 0.0750(14) Uani 1 1 d . . . . .
H5 H 0.335348 0.365707 0.074894 0.090 Uiso 1 1 calc R U . . .
C6 C 0.2604(2) 0.3720(3) 0.1732(3) 0.0583(11) Uani 1 1 d . . . . .
C7 C 0.2878(2) 0.3378(3) 0.2676(3) 0.0562(10) Uani 1 1 d . . . . .
C8 C 0.2240(2) 0.3518(3) 0.3310(4) 0.0611(11) Uani 1 1 d . . . . .
C9 C 0.2249(3) 0.3294(4) 0.4354(4) 0.0801(15) Uani 1 1 d . . . . .
H9A H 0.254778 0.373037 0.467743 0.120 Uiso 1 1 calc R U . . .
H9B H 0.241124 0.265582 0.444627 0.120 Uiso 1 1 calc R U . . .
H9C H 0.179473 0.335127 0.460815 0.120 Uiso 1 1 calc R U . . .
C10 C 0.2845(3) 0.1614(4) 0.2383(5) 0.0897(18) Uani 1 1 d . . . . .
H10A H 0.306126 0.102471 0.239679 0.108 Uiso 1 1 calc R U . . .
H10B H 0.239897 0.166342 0.215468 0.108 Uiso 1 1 calc R U . . .
C11 C 0.3165(2) 0.2368(3) 0.2685(3) 0.0617(11) Uani 1 1 d . . . . .
C12 C 0.3882(3) 0.2385(3) 0.3069(4) 0.0726(13) Uani 1 1 d . . . . .
H12A H 0.391379 0.202475 0.365960 0.087 Uiso 1 1 calc R U . . .
H12B H 0.420133 0.212188 0.260860 0.087 Uiso 1 1 calc R U . . .
C13 C 0.4637(2) 0.3730(3) 0.3540(3) 0.0620(11) Uani 1 1 d . . . . .
C14 C 0.4660(2) 0.4764(3) 0.3630(3) 0.0591(11) Uani 1 1 d . . . . .
C15 C 0.5274(2) 0.5217(4) 0.3874(3) 0.0682(13) Uani 1 1 d . . . . .
H15 H 0.566727 0.486634 0.400283 0.082 Uiso 1 1 calc R U . . .
C16 C 0.5281(3) 0.6194(4) 0.3920(3) 0.0731(14) Uani 1 1 d . . . . .
C17 C 0.4705(3) 0.6734(4) 0.3746(4) 0.0848(16) Uani 1 1 d . . . . .
H17 H 0.472106 0.739334 0.379234 0.102 Uiso 1 1 calc R U . . .
C18 C 0.4104(3) 0.6275(4) 0.3503(4) 0.0744(14) Uani 1 1 d . . . . .
H18 H 0.371204 0.663416 0.339309 0.089 Uiso 1 1 calc R U . . .
C19 C 0.4072(2) 0.5304(3) 0.3421(3) 0.0591(11) Uani 1 1 d . . . . .
C20 C 0.3480(2) 0.3975(3) 0.3033(3) 0.0520(10) 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 C16 1.893(5) . ?
O1 C13 1.229(5) . ?
N1 C1 1.436(7) . ?
N1 C8 1.255(6) . ?
N2 C12 1.472(6) . ?
N2 C13 1.354(6) . ?
N2 C20 1.362(5) . ?
N3 C19 1.394(6) . ?
N3 C20 1.285(5) . ?
C1 C2 1.363(8) . ?
C1 C6 1.398(7) . ?
C2 H2 0.9300 . ?
C2 C3 1.412(10) . ?
C3 H3 0.9300 . ?
C3 C4 1.344(10) . ?
C4 H4 0.9300 . ?
C4 C5 1.407(8) . ?
C5 H5 0.9300 . ?
C5 C6 1.362(7) . ?
C6 C7 1.502(6) . ?
C7 C8 1.543(6) . ?
C7 C11 1.526(6) . ?
C7 C20 1.529(6) . ?
C8 C9 1.492(7) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9300 . ?
C10 H10B 0.9300 . ?
C10 C11 1.302(7) . ?
C11 C12 1.500(7) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.460(7) . ?
C14 C15 1.401(6) . ?
C14 C19 1.408(7) . ?
C15 H15 0.9300 . ?
C15 C16 1.375(8) . ?
C16 C17 1.378(8) . ?
C17 H17 0.9300 . ?
C17 C18 1.382(7) . ?
C18 H18 0.9300 . ?
C18 C19 1.372(7) . ?

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 C1 108.5(4) . . ?
C13 N2 C12 123.2(4) . . ?
C13 N2 C20 123.5(4) . . ?
C20 N2 C12 113.3(4) . . ?
C20 N3 C19 115.3(4) . . ?
C2 C1 N1 126.5(5) . . ?
C2 C1 C6 122.7(5) . . ?
C6 C1 N1 110.8(4) . . ?
C1 C2 H2 122.2 . . ?
C1 C2 C3 115.5(6) . . ?
C3 C2 H2 122.2 . . ?
C2 C3 H3 118.8 . . ?
C4 C3 C2 122.4(6) . . ?
C4 C3 H3 118.8 . . ?
C3 C4 H4 119.3 . . ?
C3 C4 C5 121.4(6) . . ?
C5 C4 H4 119.3 . . ?
C4 C5 H5 121.4 . . ?
C6 C5 C4 117.1(6) . . ?
C6 C5 H5 121.4 . . ?
C1 C6 C7 106.9(4) . . ?
C5 C6 C1 120.8(5) . . ?
C5 C6 C7 132.3(4) . . ?
C6 C7 C8 100.1(4) . . ?
C6 C7 C11 115.8(4) . . ?
C6 C7 C20 112.7(3) . . ?
C11 C7 C8 114.2(4) . . ?
C11 C7 C20 103.0(3) . . ?
C20 C7 C8 111.4(3) . . ?
N1 C8 C7 113.6(4) . . ?
N1 C8 C9 124.7(5) . . ?
C9 C8 C7 121.7(4) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
H10A C10 H10B 120.0 . . ?
C11 C10 H10A 120.0 . . ?
C11 C10 H10B 120.0 . . ?
C10 C11 C7 125.3(5) . . ?
C10 C11 C12 125.3(4) . . ?
C12 C11 C7 109.4(4) . . ?
N2 C12 C11 104.3(4) . . ?
N2 C12 H12A 110.9 . . ?
N2 C12 H12B 110.9 . . ?
C11 C12 H12A 110.9 . . ?
C11 C12 H12B 110.9 . . ?
H12A C12 H12B 108.9 . . ?
O1 C13 N2 122.4(4) . . ?
O1 C13 C14 124.4(4) . . ?
N2 C13 C14 113.3(4) . . ?
C15 C14 C13 120.0(4) . . ?
C15 C14 C19 120.3(4) . . ?
C19 C14 C13 119.6(4) . . ?
C14 C15 H15 120.8 . . ?
C16 C15 C14 118.3(5) . . ?
C16 C15 H15 120.8 . . ?
C15 C16 Br1 119.2(5) . . ?
C15 C16 C17 122.2(5) . . ?
C17 C16 Br1 118.5(4) . . ?
C16 C17 H17 120.6 . . ?
C16 C17 C18 118.7(5) . . ?
C18 C17 H17 120.6 . . ?
C17 C18 H18 119.2 . . ?
C19 C18 C17 121.6(6) . . ?
C19 C18 H18 119.2 . . ?
N3 C19 C14 122.1(4) . . ?
C18 C19 N3 119.1(4) . . ?
C18 C19 C14 118.8(4) . . ?
N2 C20 C7 110.0(3) . . ?
N3 C20 N2 126.3(4) . . ?
N3 C20 C7 123.7(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 C16 C17 C18 177.7(4) . . . . ?
O1 C13 C14 C15 4.2(7) . . . . ?
O1 C13 C14 C19 -179.0(5) . . . . ?
N1 C1 C2 C3 -179.8(5) . . . . ?
N1 C1 C6 C5 -179.1(4) . . . . ?
N1 C1 C6 C7 0.3(5) . . . . ?
N2 C13 C14 C15 -175.9(4) . . . . ?
N2 C13 C14 C19 0.8(6) . . . . ?
C1 N1 C8 C7 -1.6(5) . . . . ?
C1 N1 C8 C9 178.9(4) . . . . ?
C1 C2 C3 C4 -0.8(9) . . . . ?
C1 C6 C7 C8 -1.1(4) . . . . ?
C1 C6 C7 C11 122.3(4) . . . . ?
C1 C6 C7 C20 -119.5(4) . . . . ?
C2 C1 C6 C5 1.5(7) . . . . ?
C2 C1 C6 C7 -179.1(5) . . . . ?
C2 C3 C4 C5 1.2(10) . . . . ?
C3 C4 C5 C6 -0.3(8) . . . . ?
C4 C5 C6 C1 -1.0(7) . . . . ?
C4 C5 C6 C7 179.7(4) . . . . ?
C5 C6 C7 C8 178.3(5) . . . . ?
C5 C6 C7 C11 -58.3(6) . . . . ?
C5 C6 C7 C20 59.9(6) . . . . ?
C6 C1 C2 C3 -0.5(8) . . . . ?
C6 C7 C8 N1 1.7(5) . . . . ?
C6 C7 C8 C9 -178.7(4) . . . . ?
C6 C7 C11 C10 -52.5(7) . . . . ?
C6 C7 C11 C12 125.9(4) . . . . ?
C6 C7 C20 N2 -126.9(4) . . . . ?
C6 C7 C20 N3 52.7(6) . . . . ?
C7 C11 C12 N2 -2.6(5) . . . . ?
C8 N1 C1 C2 -179.8(5) . . . . ?
C8 N1 C1 C6 0.8(5) . . . . ?
C8 C7 C11 C10 63.1(7) . . . . ?
C8 C7 C11 C12 -118.5(4) . . . . ?
C8 C7 C20 N2 121.5(4) . . . . ?
C8 C7 C20 N3 -58.9(6) . . . . ?
C10 C11 C12 N2 175.8(5) . . . . ?
C11 C7 C8 N1 -122.8(4) . . . . ?
C11 C7 C8 C9 56.8(5) . . . . ?
C11 C7 C20 N2 -1.4(5) . . . . ?
C11 C7 C20 N3 178.2(4) . . . . ?
C12 N2 C13 O1 -1.9(7) . . . . ?
C12 N2 C13 C14 178.2(4) . . . . ?
C12 N2 C20 N3 -179.8(4) . . . . ?
C12 N2 C20 C7 -0.2(5) . . . . ?
C13 N2 C12 C11 -176.1(4) . . . . ?
C13 N2 C20 N3 -1.9(7) . . . . ?
C13 N2 C20 C7 177.7(4) . . . . ?
C13 C14 C15 C16 177.8(4) . . . . ?
C13 C14 C19 N3 -1.1(6) . . . . ?
C13 C14 C19 C18 -179.6(4) . . . . ?
C14 C15 C16 Br1 -177.9(3) . . . . ?
C14 C15 C16 C17 0.9(7) . . . . ?
C15 C14 C19 N3 175.6(4) . . . . ?
C15 C14 C19 C18 -2.8(7) . . . . ?
C15 C16 C17 C18 -1.1(8) . . . . ?
C16 C17 C18 C19 -0.8(8) . . . . ?
C17 C18 C19 N3 -175.8(5) . . . . ?
C17 C18 C19 C14 2.7(8) . . . . ?
C19 N3 C20 N2 1.6(6) . . . . ?
C19 N3 C20 C7 -177.9(4) . . . . ?
C19 C14 C15 C16 1.1(7) . . . . ?
C20 N2 C12 C11 1.8(6) . . . . ?
C20 N2 C13 O1 -179.6(4) . . . . ?
C20 N2 C13 C14 0.5(6) . . . . ?
C20 N3 C19 C14 -0.1(6) . . . . ?
C20 N3 C19 C18 178.4(4) . . . . ?
C20 C7 C8 N1 121.1(4) . . . . ?
C20 C7 C8 C9 -59.3(5) . . . . ?
C20 C7 C11 C10 -176.0(5) . . . . ?
C20 C7 C11 C12 2.4(5) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.500 -0.849 343.8 87.6 ?
2 0.500 0.000 -0.689 343.8 87.6 ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.864
_oxdiff_exptl_absorpt_empirical_full_min 0.656
