# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_pk_1
_database_code_depnum_ccdc_archive 'CCDC 1948449'
loop_
_audit_author_name
_audit_author_address
'Prof. Patrick McArdle'
;National University of Ireland, Galway
Republic of Ireland
;
_audit_update_record             
;
2019-08-21 deposited with the CCDC.	2021-02-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H18 Cl2 N4 O4'
_chemical_formula_weight         449.28

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'
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   10.7210(7)
_cell_length_b                   14.6163(11)
_cell_length_c                   12.7288(11)
_cell_angle_alpha                90
_cell_angle_beta                 97.406(7)
_cell_angle_gamma                90
_cell_volume                     1978.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    299.0(1)
_cell_measurement_reflns_used    2161
_cell_measurement_theta_min      3.8430
_cell_measurement_theta_max      28.7590

_exptl_crystal_description       Parallelepiped
_exptl_crystal_colour            Red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.509
_exptl_crystal_F_000             928
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    0.365
_shelx_estimated_absorpt_T_min   0.838
_shelx_estimated_absorpt_T_max   0.931
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.93128
_exptl_absorpt_correction_T_max  1.00000
_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) 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      299.0(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'enhance (mo) x-ray source'
_diffrn_measurement_device_type  'xcalibur, sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.1048
_diffrn_reflns_number            9557
_diffrn_reflns_av_unetI/netI     0.0779
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.383
_diffrn_reflns_theta_max         29.242
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.852
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.852
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.852
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4593
_reflns_number_gt                2698
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       
; 
crysalispro, agilent technologies, 
version 1.171.37.35 (release 13-08-2014 crysalis171 .net) 
(compiled aug 13 2014,18:06:01) 
;
_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_reduction        
; 
crysalispro, agilent technologies, 
version 1.171.37.35 (release 13-08-2014 crysalis171 .net) 
(compiled aug 13 2014,18:06:01) 
;
_computing_structure_solution    
'SHELXT - G.M.Sheldrick,Acta Crystallogr.A71(2015)3-8.'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
'ORTEX - P. McArdle, J.Appl.Cryst.,1995,28,65-65.'
_computing_publication_material  ?
_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)+(0.0672P)²+0.1211P] 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_number_reflns         4593
_refine_ls_number_parameters     275
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1107
_refine_ls_R_factor_gt           0.0599
_refine_ls_wR_factor_ref         0.1726
_refine_ls_wR_factor_gt          0.1393
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_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
Cl1 Cl 1.10528(10) 0.53289(7) 0.75188(8) 0.0744(4) Uani 1 1 d . . . . .
Cl2 Cl -0.17505(8) 0.13832(8) 0.47285(8) 0.0694(3) Uani 1 1 d . . . . .
O1 O 0.84995(19) 0.16660(14) 0.80561(16) 0.0467(6) Uani 1 1 d . . . . .
O2 O 0.57349(19) 0.38426(14) 0.49939(17) 0.0480(6) Uani 1 1 d . . . . .
O4 O 0.34996(19) 0.33620(14) 0.63245(17) 0.0479(6) Uani 1 1 d . . . . .
O3 O 0.3471(2) 0.02895(14) 0.4015(2) 0.0608(7) Uani 1 1 d . . . . .
N2 N 0.8509(2) 0.42036(15) 0.58740(19) 0.0377(6) Uani 1 1 d . . . . .
N1 N 0.9558(2) 0.32831(16) 0.70885(17) 0.0340(5) Uani 1 1 d . . . . .
N3 N 0.1136(2) 0.14253(16) 0.40925(17) 0.0346(6) Uani 1 1 d . . . . .
N4 N 0.1159(2) 0.27063(17) 0.5058(2) 0.0411(6) Uani 1 1 d . . . . .
C1 C 0.8357(2) 0.29366(18) 0.6899(2) 0.0316(6) Uani 1 1 d . . . . .
C2 C 0.7793(3) 0.21792(18) 0.7307(2) 0.0336(6) Uani 1 1 d . . . . .
C3 C 0.6573(3) 0.19991(19) 0.6891(2) 0.0346(6) Uani 1 1 d . . . . .
H3 H 0.6171 0.1494 0.7138 0.045 Uiso 1 1 calc R U . . .
C4 C 0.5906(2) 0.25528(18) 0.6100(2) 0.0316(6) Uani 1 1 d . . . . .
C5 C 0.6443(2) 0.33253(18) 0.5726(2) 0.0326(6) Uani 1 1 d . . . . .
C6 C 0.7713(3) 0.35150(17) 0.6141(2) 0.0311(6) Uani 1 1 d . . . . .
C7 C 0.9586(3) 0.40330(19) 0.6453(2) 0.0355(7) Uani 1 1 d . . . . .
C8 C 0.4674(2) 0.22071(18) 0.5590(2) 0.0315(6) Uani 1 1 d . . . . .
C9 C 0.4618(3) 0.14152(19) 0.5062(2) 0.0383(7) Uani 1 1 d . . . . .
H9 H 0.5364 0.1092 0.5053 0.050 Uiso 1 1 calc R U . . .
C10 C 0.3461(3) 0.10158(19) 0.4491(2) 0.0364(7) Uani 1 1 d . . . . .
C11 C 0.2349(3) 0.15638(18) 0.4545(2) 0.0322(6) Uani 1 1 d . . . . .
C12 C 0.2344(2) 0.23434(19) 0.5133(2) 0.0323(6) Uani 1 1 d . . . . .
C13 C 0.3492(3) 0.27152(18) 0.5723(2) 0.0334(6) Uani 1 1 d . . . . .
C14 C 0.0470(3) 0.2135(2) 0.4426(2) 0.0381(7) Uani 1 1 d . . . . .
C15 C 1.0653(3) 0.2870(2) 0.7707(3) 0.0491(8) Uani 1 1 d . . . . .
H15A H 1.1033 0.2440 0.7275 0.064 Uiso 1 1 calc R U . . .
H15B H 1.0398 0.2560 0.8309 0.064 Uiso 1 1 calc R U . . .
H15C H 1.1251 0.3339 0.7945 0.064 Uiso 1 1 calc R U . . .
C16 C 0.7903(3) 0.08952(19) 0.8446(2) 0.0442(8) Uani 1 1 d . . . . .
H16A H 0.7183 0.1092 0.8763 0.057 Uiso 1 1 calc R U . . .
H16B H 0.8483 0.0588 0.8967 0.057 Uiso 1 1 calc R U . . .
H16C H 0.7639 0.0484 0.7872 0.057 Uiso 1 1 calc R U . . .
C17 C 0.6318(3) 0.4283(2) 0.4190(2) 0.0490(8) Uani 1 1 d . . . . .
H17A H 0.6770 0.4811 0.4481 0.064 Uiso 1 1 calc R U . . .
H17B H 0.5686 0.4468 0.3626 0.064 Uiso 1 1 calc R U . . .
H17C H 0.6891 0.3867 0.3919 0.064 Uiso 1 1 calc R U . . .
C18 C 1.0738(3) 0.4572(2) 0.6404(2) 0.0428(7) Uani 1 1 d . . . . .
H18A H 1.0648 0.4927 0.5755 0.056 Uiso 1 1 calc R U . . .
H18B H 1.1445 0.4160 0.6388 0.056 Uiso 1 1 calc R U . . .
C19 C 0.0662(3) 0.0701(2) 0.3362(3) 0.0518(9) Uani 1 1 d . . . . .
H19A H 0.0447 0.0177 0.3757 0.067 Uiso 1 1 calc R U . . .
H19B H 0.1299 0.0535 0.2932 0.067 Uiso 1 1 calc R U . . .
H19C H -0.0071 0.0914 0.2917 0.067 Uiso 1 1 calc R U . . .
C20 C -0.0904(3) 0.2232(2) 0.4110(3) 0.0499(8) Uani 1 1 d . . . . .
H20A H -0.1091 0.2175 0.3347 0.065 Uiso 1 1 calc R U . . .
H20B H -0.1172 0.2835 0.4309 0.065 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
Cl1 C18 1.797(3) . ?
Cl2 C20 1.779(4) . ?
O1 C2 1.363(3) . ?
O1 C16 1.417(3) . ?
O2 C5 1.354(3) . ?
O2 C17 1.420(3) . ?
O4 C13 1.216(3) . ?
O3 C10 1.223(3) . ?
N2 C7 1.311(3) . ?
N2 C6 1.390(3) . ?
N1 C7 1.365(3) . ?
N1 C1 1.376(3) . ?
N1 C15 1.458(3) . ?
N3 C14 1.358(3) . ?
N3 C11 1.368(3) . ?
N3 C19 1.456(3) . ?
N4 C14 1.318(3) . ?
N4 C12 1.369(3) . ?
C1 C2 1.394(4) . ?
C1 C6 1.396(4) . ?
C2 C3 1.372(4) . ?
C3 C4 1.412(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.380(4) . ?
C4 C8 1.484(4) . ?
C5 C6 1.423(4) . ?
C7 C18 1.473(4) . ?
C8 C9 1.336(4) . ?
C8 C13 1.498(4) . ?
C9 C10 1.475(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.445(4) . ?
C11 C12 1.364(4) . ?
C12 C13 1.461(4) . ?
C14 C20 1.483(4) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?

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 O1 C16 116.6(2) . . ?
C5 O2 C17 119.3(2) . . ?
C7 N2 C6 104.4(2) . . ?
C7 N1 C1 106.5(2) . . ?
C7 N1 C15 125.1(2) . . ?
C1 N1 C15 127.8(2) . . ?
C14 N3 C11 105.4(2) . . ?
C14 N3 C19 126.9(2) . . ?
C11 N3 C19 127.6(2) . . ?
C14 N4 C12 103.9(2) . . ?
N1 C1 C2 132.0(2) . . ?
N1 C1 C6 105.4(2) . . ?
C2 C1 C6 122.6(2) . . ?
O1 C2 C3 125.5(3) . . ?
O1 C2 C1 117.9(2) . . ?
C3 C2 C1 116.5(2) . . ?
C2 C3 C4 122.4(3) . . ?
C2 C3 H3 118.8 . . ?
C4 C3 H3 118.8 . . ?
C5 C4 C3 121.3(2) . . ?
C5 C4 C8 121.0(2) . . ?
C3 C4 C8 117.2(2) . . ?
O2 C5 C4 118.2(2) . . ?
O2 C5 C6 124.9(2) . . ?
C4 C5 C6 116.9(2) . . ?
N2 C6 C1 110.1(2) . . ?
N2 C6 C5 129.6(2) . . ?
C1 C6 C5 120.2(2) . . ?
N2 C7 N1 113.6(3) . . ?
N2 C7 C18 123.9(3) . . ?
N1 C7 C18 122.5(3) . . ?
C9 C8 C4 119.7(3) . . ?
C9 C8 C13 120.2(3) . . ?
C4 C8 C13 120.0(2) . . ?
C8 C9 C10 124.8(3) . . ?
C8 C9 H9 117.6 . . ?
C10 C9 H9 117.6 . . ?
O3 C10 C11 124.4(3) . . ?
O3 C10 C9 121.8(3) . . ?
C11 C10 C9 113.8(2) . . ?
C12 C11 N3 106.5(2) . . ?
C12 C11 C10 123.5(3) . . ?
N3 C11 C10 130.0(2) . . ?
C11 C12 N4 110.8(2) . . ?
C11 C12 C13 122.0(2) . . ?
N4 C12 C13 127.2(3) . . ?
O4 C13 C12 123.4(3) . . ?
O4 C13 C8 121.3(3) . . ?
C12 C13 C8 115.2(2) . . ?
N4 C14 N3 113.5(2) . . ?
N4 C14 C20 124.3(3) . . ?
N3 C14 C20 122.2(3) . . ?
N1 C15 H15A 109.5 . . ?
N1 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N1 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O1 C16 H16A 109.5 . . ?
O1 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O1 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O2 C17 H17A 109.5 . . ?
O2 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O2 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C7 C18 Cl1 111.6(2) . . ?
C7 C18 H18A 109.3 . . ?
Cl1 C18 H18A 109.3 . . ?
C7 C18 H18B 109.3 . . ?
Cl1 C18 H18B 109.3 . . ?
H18A C18 H18B 108.0 . . ?
N3 C19 H19A 109.5 . . ?
N3 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N3 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C14 C20 Cl2 111.1(2) . . ?
C14 C20 H20A 109.4 . . ?
Cl2 C20 H20A 109.4 . . ?
C14 C20 H20B 109.4 . . ?
Cl2 C20 H20B 109.4 . . ?
H20A C20 H20B 108.0 . . ?

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
C7 N1 C1 C2 179.1(3) . . . . ?
C15 N1 C1 C2 8.1(5) . . . . ?
C7 N1 C1 C6 -0.1(3) . . . . ?
C15 N1 C1 C6 -171.2(3) . . . . ?
C16 O1 C2 C3 -1.5(4) . . . . ?
C16 O1 C2 C1 -179.3(2) . . . . ?
N1 C1 C2 O1 1.8(4) . . . . ?
C6 C1 C2 O1 -179.1(2) . . . . ?
N1 C1 C2 C3 -176.3(3) . . . . ?
C6 C1 C2 C3 2.9(4) . . . . ?
O1 C2 C3 C4 -178.7(3) . . . . ?
C1 C2 C3 C4 -0.8(4) . . . . ?
C2 C3 C4 C5 -1.9(4) . . . . ?
C2 C3 C4 C8 170.3(3) . . . . ?
C17 O2 C5 C4 -145.1(3) . . . . ?
C17 O2 C5 C6 34.6(4) . . . . ?
C3 C4 C5 O2 -177.7(2) . . . . ?
C8 C4 C5 O2 10.4(4) . . . . ?
C3 C4 C5 C6 2.5(4) . . . . ?
C8 C4 C5 C6 -169.4(2) . . . . ?
C7 N2 C6 C1 0.2(3) . . . . ?
C7 N2 C6 C5 -176.6(3) . . . . ?
N1 C1 C6 N2 -0.1(3) . . . . ?
C2 C1 C6 N2 -179.4(2) . . . . ?
N1 C1 C6 C5 177.1(2) . . . . ?
C2 C1 C6 C5 -2.3(4) . . . . ?
O2 C5 C6 N2 -3.8(5) . . . . ?
C4 C5 C6 N2 176.0(3) . . . . ?
O2 C5 C6 C1 179.7(3) . . . . ?
C4 C5 C6 C1 -0.5(4) . . . . ?
C6 N2 C7 N1 -0.3(3) . . . . ?
C6 N2 C7 C18 177.6(3) . . . . ?
C1 N1 C7 N2 0.3(3) . . . . ?
C15 N1 C7 N2 171.7(3) . . . . ?
C1 N1 C7 C18 -177.6(2) . . . . ?
C15 N1 C7 C18 -6.3(4) . . . . ?
C5 C4 C8 C9 111.6(3) . . . . ?
C3 C4 C8 C9 -60.6(4) . . . . ?
C5 C4 C8 C13 -72.2(4) . . . . ?
C3 C4 C8 C13 115.6(3) . . . . ?
C4 C8 C9 C10 -177.8(3) . . . . ?
C13 C8 C9 C10 6.0(4) . . . . ?
C8 C9 C10 O3 179.5(3) . . . . ?
C8 C9 C10 C11 0.0(4) . . . . ?
C14 N3 C11 C12 0.6(3) . . . . ?
C19 N3 C11 C12 177.6(3) . . . . ?
C14 N3 C11 C10 178.4(3) . . . . ?
C19 N3 C11 C10 -4.7(5) . . . . ?
O3 C10 C11 C12 175.8(3) . . . . ?
C9 C10 C11 C12 -4.7(4) . . . . ?
O3 C10 C11 N3 -1.6(5) . . . . ?
C9 C10 C11 N3 177.9(3) . . . . ?
N3 C11 C12 N4 -0.5(3) . . . . ?
C10 C11 C12 N4 -178.4(3) . . . . ?
N3 C11 C12 C13 -179.0(2) . . . . ?
C10 C11 C12 C13 3.0(4) . . . . ?
C14 N4 C12 C11 0.1(3) . . . . ?
C14 N4 C12 C13 178.6(3) . . . . ?
C11 C12 C13 O4 -173.5(3) . . . . ?
N4 C12 C13 O4 8.2(5) . . . . ?
C11 C12 C13 C8 3.0(4) . . . . ?
N4 C12 C13 C8 -175.3(3) . . . . ?
C9 C8 C13 O4 169.2(3) . . . . ?
C4 C8 C13 O4 -7.0(4) . . . . ?
C9 C8 C13 C12 -7.4(4) . . . . ?
C4 C8 C13 C12 176.4(2) . . . . ?
C12 N4 C14 N3 0.3(3) . . . . ?
C12 N4 C14 C20 179.2(3) . . . . ?
C11 N3 C14 N4 -0.6(3) . . . . ?
C19 N3 C14 N4 -177.6(3) . . . . ?
C11 N3 C14 C20 -179.5(3) . . . . ?
C19 N3 C14 C20 3.5(5) . . . . ?
N2 C7 C18 Cl1 103.7(3) . . . . ?
N1 C7 C18 Cl1 -78.6(3) . . . . ?
N4 C14 C20 Cl2 -108.6(3) . . . . ?
N3 C14 C20 Cl2 70.2(3) . . . . ?

_refine_diff_density_max         0.383
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.056

####################################################################### 
# 
# 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_exp_2141
_database_code_depnum_ccdc_archive 'CCDC 2022190'
loop_
_audit_author_name
_audit_author_address
'Jeremy Karl Cockcroft'
;University College London
United Kingdom
;
_audit_update_record             
;
2020-08-07 deposited with the CCDC.	2021-02-26 downloaded from the CCDC.
;
_audit_creation_date             2020-06-02
_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        
8''-chloro-6'',9''-dimethoxy-8-(trifluoromethyl)-[7,7''-bipyrido[1,2-a]benzimidazole]-6,9-dione
_chemical_formula_moiety         'C25 H22 Cl F3 N4 O4'
_chemical_formula_sum            'C25 H22 Cl F3 N4 O4'
_chemical_formula_weight         534.91
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C25 H22 Cl1 F3 N4 O4 '
_chemical_oxdiff_usercomment     'DC035E: Dark Orange Crystal Cut from Lump'
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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 '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                   16.9129(3)
_cell_length_b                   16.4330(2)
_cell_length_c                   8.5648(2)
_cell_angle_alpha                90
_cell_angle_beta                 104.382(2)
_cell_angle_gamma                90
_cell_volume                     2305.81(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    19262
_cell_measurement_temperature    100
_cell_measurement_theta_max      72.4870
_cell_measurement_theta_min      5.3600
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.065
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.882
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.76a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear dark orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.541
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1104
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
7 -7 1 0.0689
1 -11 0 0.0594
1 -5 -5 0.0505
11 -1 -2 0.0533
-7 1 5 0.0498
7 3 -5 0.0456
1 8 3 0.0453
0 -10 -1 0.0546
-6 -8 2 0.0724
-8 0 5 0.0499
0 -2 -5 0.0395
-10 4 1 0.0510
0 2 5 0.0395
9 -3 2 0.0561
-7 2 -3 0.0525
11 1 0 0.0543
-10 -2 0 0.0545
2 10 1 0.0498
0 11 -1 0.0518
2 -9 2 0.0596
-2 0 6 0.0359
1 1 -5 0.0290

_exptl_crystal_size_max          0.118
_exptl_crystal_size_mid          0.112
_exptl_crystal_size_min          0.069
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
6.8480 -7.4839 0.9896 -0.4967 -0.7503 -0.4362
0.5125 -10.6266 -0.4377 -0.8832 -0.0866 -0.4610
0.6233 -4.6563 -4.9161 -0.1995 0.5571 -0.8062
10.8693 -1.3971 -1.6536 0.2331 -0.6607 -0.7135
-7.4358 1.1235 4.8595 -0.2846 -0.0410 0.9578
7.1452 2.6506 -4.7637 0.5976 0.0884 -0.7969
1.0231 8.3024 3.2161 0.6206 -0.4271 0.6576
-0.0600 -10.2745 -1.4363 -0.8309 0.0949 -0.5483
-6.0288 -8.4573 2.1755 -0.9699 0.1093 0.2178
-8.2220 -0.0821 4.6054 -0.3998 0.0436 0.9156
0.3755 -1.5954 -5.3706 0.0740 0.6670 -0.7413
-9.9481 4.4967 1.0618 0.0801 0.6961 0.7135
-0.3755 1.5954 5.3706 -0.0740 -0.6670 0.7413
8.7411 -3.2425 1.7163 -0.1087 -0.9562 -0.2719
-6.9636 2.1067 -3.1486 0.1123 0.9934 -0.0221
10.6571 0.9672 -0.1432 0.3741 -0.8211 -0.4312
-10.4608 -1.7557 -0.0565 -0.4291 0.8242 0.3695
1.5124 10.2127 1.1722 0.8744 -0.1763 0.4521
-0.3243 10.5533 -0.7120 0.9250 0.2235 0.3075
1.9190 -9.2118 2.3007 -0.8264 -0.5483 -0.1284
-1.5913 -0.4972 5.5242 -0.2922 -0.6110 0.7358
0.9690 0.9729 -5.4649 0.3141 0.6574 -0.6850

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0484
_diffrn_reflns_av_unetI/netI     0.0211
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            38841
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.692
_diffrn_reflns_theta_min         3.810
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2031
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -5.00  20.00   1.00    1.00    --   34.00  94.00-102.97   25
  2  ω     -4.00  21.00   1.00    1.00    --   34.00  91.00  94.18   25
  3  ω      2.00  27.00   1.00    1.00    --   38.00  87.00 -41.98   25
  4  ω   -116.00 -31.00   1.00    1.00    --  -42.62 -38.00 -90.00   85
  5  ω   -117.00 -18.00   1.00    1.00    --  -42.62 -38.00   0.00   99
  6  ω   -105.00 -79.00   1.00    1.00    --  -42.62 -38.00  90.00   26
  7  ω    -71.00  31.00   1.00    1.00    --  -42.62  57.00  60.00  102
  8  ω    -56.00 -20.00   1.00    1.00    --  -42.62 -38.00  90.00   36
  9  ω     -2.00  70.00   1.00    1.00    --   42.62 -57.00-150.00   72
 10  ω     28.00  99.00   1.00    1.00    --   42.62-125.00-180.00   71
 11  ω     10.00  35.00   1.00    1.00    --   42.62  75.00-175.24   25
 12  ω     13.00  41.00   1.00    1.00    --   46.00  79.00  19.71   28
 13  ω     15.00  41.00   1.00    1.00    --   46.00  76.00 115.71   26
 14  ω     13.00  38.00   1.00    1.00    --   46.00  79.00-158.99   25
 15  ω     31.00  58.00   1.00    1.00    --   62.00  72.00 121.42   27
 16  ω     30.00  57.00   1.00    1.00    --   62.00  74.00 172.16   27
 17  ω     34.00  60.00   1.00    1.00    --   66.00  74.00 -63.53   26
 18  ω    101.00 128.00   1.00    1.00    --   66.00  74.00 -63.53   27
 19  ω     34.00  60.00   1.00    1.00    --   66.00  73.00  51.69   26
 20  ω     34.00  66.00   1.00    1.00    --   66.00  74.00-126.71   32
 21  ω     39.00  76.00   1.00    1.00    --   70.00  72.00-155.86   37
 22  ω     39.00  65.00   1.00    1.00    --   70.00  70.00   5.25   26
 23  ω     39.00  65.00   1.00    1.00    --   70.00  70.00 -29.42   26
 24  ω     42.00  76.00   1.00    2.00    --   74.00  74.00-112.73   34
 25  ω     42.00  68.00   1.00    2.00    --   74.00  73.00  58.36   26
 26  ω     42.00  68.00   1.00    2.00    --   74.00  74.00  73.45   26
 27  ω     48.00  74.00   1.00    2.00    --   78.00  68.00 136.26   26
 28  ω     50.00  76.00   1.00    2.00    --   78.00  55.00 133.81   26
 29  ω     52.00  77.00   1.00    2.00    --   82.00  72.00   1.43   25
 30  ω     52.00  81.00   1.00    2.00    --   82.00  66.00 -51.22   29
 31  ω     54.00  89.00   1.00    2.00    --   86.00  74.00 152.90   35
 32  ω     61.00  87.00   1.00    2.00    --   90.00  59.00  63.16   26
 33  ω    116.00 163.00   1.00    2.00    --   90.00  66.00  68.67   47
 34  ω     60.00  87.00   1.00    2.00    --   90.00  66.00  68.67   27
 35  ω     63.00  96.00   1.00    2.00    --   90.00  64.00-130.15   33
 36  ω     59.00  85.00   1.00    2.00    --   90.00  69.00 128.32   26
 37  ω     69.00 166.00   1.00    2.00    --   98.00  59.00  28.51   97
 38  ω     73.00 173.00   1.00    2.00    --  104.49  74.00-109.40  100
 39  ω     37.00 107.00   1.00    2.00    --  104.49-100.00 -25.87   70
 40  ω     75.00 155.00   1.00    2.00    --  104.49  61.00   0.00   80
 41  ω     83.00 164.00   1.00    2.00    --  104.49  61.00-150.00   81
 42  ω     77.00 141.00   1.00    2.00    --  104.49  70.00 -26.66   64
 43  ω     73.00 174.00   1.00    2.00    --  104.49  73.00 176.99  101
 44  ω     76.00 115.00   1.00    2.00    --  104.49  61.00-180.00   39
 45  ω     75.00 124.00   1.00    2.00    --  104.49  61.00 150.00   49
 46  ω    130.00 163.00   1.00    2.00    --  104.49 125.00 150.00   33
 47  ω     75.00 101.00   1.00    2.00    --  104.49  63.00 -42.93   26
 48  ω    108.00 176.00   1.00    2.00    --  104.49  61.00 -60.00   68
 49  ω    140.00 173.00   1.00    2.00    --  104.49  69.00  71.50   33
 50  ω     75.00 103.00   1.00    2.00    --  104.49  61.00 -60.00   28
 51  ω     74.00 129.00   1.00    2.00    --  104.49  69.00  71.50   55
 52  ω     82.00 177.00   1.00    2.00    --  104.49  45.00 120.00   95
 53  ω     55.00 112.00   1.00    2.00    --  104.49 -45.00 120.00   57
 54  ω     97.00 148.00   1.00    2.00    --  104.49 125.00 120.00   51
 55  ω     32.00 111.00   1.00    2.00    --  104.49-125.00 -60.00   79
 56  ω     41.00 111.00   1.00    2.00    --  104.49-125.00 120.00   70
 57  ω     39.00 103.00   1.00    2.00    --  104.49 -94.00 150.00   64
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0268006000
_diffrn_orient_matrix_UB_12      0.0859443000
_diffrn_orient_matrix_UB_13      -0.0374313000
_diffrn_orient_matrix_UB_21      -0.0797126000
_diffrn_orient_matrix_UB_22      0.0097730000
_diffrn_orient_matrix_UB_23      -0.1326797000
_diffrn_orient_matrix_UB_31      -0.0420763000
_diffrn_orient_matrix_UB_32      0.0362288000
_diffrn_orient_matrix_UB_33      0.1243315000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4063
_reflns_number_total             4551
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_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 1.171.40.76a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.76a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.76a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.708
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     422
_refine_ls_number_reflns         4551
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0378
_refine_ls_restrained_S_all      1.055
_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)+(0.0515P)²+1.6916P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0970
_refine_ls_wR_factor_ref         0.1019
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_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
Cl1 Cl 0.41689(2) 0.53018(2) 0.84942(5) 0.02207(12) Uani 1 1 d . . . . .
F1 F 0.32813(7) 0.65854(6) 0.33211(12) 0.0263(2) Uani 1 1 d . . . . .
F2 F 0.41412(6) 0.67346(6) 0.56260(13) 0.0266(2) Uani 1 1 d . . . . .
F3 F 0.37861(6) 0.55410(6) 0.46983(13) 0.0251(2) Uani 1 1 d . . . . .
O1 O 0.27556(8) 0.77564(7) 0.50893(16) 0.0244(3) Uani 1 1 d . . . . .
O2 O 0.15488(8) 0.52003(7) 0.76786(17) 0.0261(3) Uani 1 1 d . . . . .
O3 O 0.15878(7) 0.45477(7) 0.43847(15) 0.0217(3) Uani 1 1 d . . . . .
O4 O 0.44824(7) 0.35241(7) 0.86383(15) 0.0217(3) Uani 1 1 d . . . . .
N1 N 0.07429(9) 0.67948(9) 0.74153(19) 0.0228(3) Uani 1 1 d . . . . .
N2 N 0.12823(9) 0.78850(8) 0.64920(18) 0.0201(3) Uani 1 1 d . . . . .
N3 N 0.20521(9) 0.27190(9) 0.49451(19) 0.0230(3) Uani 1 1 d . . . . .
N4 N 0.32327(9) 0.23511(8) 0.66561(18) 0.0211(3) Uani 1 1 d . . . . .
C1 C 0.24986(10) 0.56713(10) 0.6231(2) 0.0166(3) Uani 1 1 d . . . . .
C2 C 0.28009(10) 0.63254(10) 0.5624(2) 0.0175(3) Uani 1 1 d . . . . .
C3 C 0.24587(10) 0.71796(10) 0.5635(2) 0.0179(3) Uani 1 1 d . . . . .
C4 C 0.17508(10) 0.72284(10) 0.6303(2) 0.0180(3) Uani 1 1 d . . . . .
C5 C 0.14090(10) 0.65725(10) 0.6879(2) 0.0187(3) Uani 1 1 d . . . . .
C6 C 0.17723(10) 0.57673(10) 0.6984(2) 0.0182(3) Uani 1 1 d . . . . .
C7 C 0.27957(10) 0.48165(10) 0.6306(2) 0.0165(3) Uani 1 1 d . . . . .
C8 C 0.35379(10) 0.45721(10) 0.7363(2) 0.0180(3) Uani 1 1 d . . . . .
C9 C 0.37663(10) 0.37619(10) 0.7582(2) 0.0184(3) Uani 1 1 d . . . . .
C10 C 0.32125(10) 0.31935(10) 0.6720(2) 0.0180(3) Uani 1 1 d . . . . .
C11 C 0.24705(10) 0.34123(10) 0.5643(2) 0.0189(3) Uani 1 1 d . . . . .
C12 C 0.22647(10) 0.42400(10) 0.5433(2) 0.0179(3) Uani 1 1 d . . . . .
C13 C 0.08812(11) 0.40365(12) 0.3921(3) 0.0286(4) Uani 1 1 d . . . . .
H13A H 0.0427(17) 0.4387(16) 0.339(3) 0.044(7) Uiso 1 1 d . . . . .
H13B H 0.0982(16) 0.3604(17) 0.318(3) 0.044(7) Uiso 1 1 d . . . . .
H13C H 0.0789(16) 0.3834(17) 0.484(3) 0.046(7) Uiso 1 1 d . . . . .
C14 C 0.51732(11) 0.35518(12) 0.7939(3) 0.0264(4) Uani 1 1 d . . . . .
H14A H 0.5651(14) 0.3367(13) 0.878(3) 0.027(5) Uiso 1 1 d . . . . .
H14B H 0.5268(15) 0.4115(16) 0.764(3) 0.038(6) Uiso 1 1 d . . . . .
H14C H 0.5071(14) 0.3196(14) 0.700(3) 0.030(6) Uiso 1 1 d . . . . .
C15 C 0.06827(10) 0.75901(11) 0.7153(2) 0.0227(4) Uani 1 1 d . . . . .
C16 C 0.00117(12) 0.81161(12) 0.7446(3) 0.0296(4) Uani 1 1 d . . . . .
H16A H -0.0092(11) 0.7877(11) 0.847(2) 0.009(4) Uiso 1 1 d . . . . .
H16B H -0.0454(16) 0.7990(15) 0.659(3) 0.040(7) Uiso 1 1 d . . . . .
C17 C 0.02229(12) 0.90173(12) 0.7411(3) 0.0313(4) Uani 1 1 d . . . . .
H17A H 0.0628(14) 0.9157(13) 0.844(3) 0.027(5) Uiso 1 1 d . . . . .
H17B H -0.0268(15) 0.9329(15) 0.726(3) 0.038(6) Uiso 1 1 d . . . . .
C18 C 0.06057(13) 0.92031(12) 0.6028(3) 0.0302(4) Uani 1 1 d . . . . .
H18A H 0.0200(15) 0.9049(15) 0.497(3) 0.037(6) Uiso 1 1 d . . . . .
H18B H 0.0775(15) 0.9713(16) 0.597(3) 0.036(6) Uiso 1 1 d . . . . .
C19 C 0.14041(12) 0.87561(10) 0.6186(2) 0.0244(4) Uani 1 1 d . . . . .
H19A H 0.1606(13) 0.8784(12) 0.530(3) 0.018(5) Uiso 1 1 d . . . . .
H19B H 0.1833(15) 0.8987(14) 0.705(3) 0.032(6) Uiso 1 1 d . . . . .
C20 C 0.35021(10) 0.62894(10) 0.4828(2) 0.0201(3) Uani 1 1 d . . . . .
C21 C 0.25251(11) 0.21119(10) 0.5602(2) 0.0225(4) Uani 1 1 d . . . . .
C22 C 0.23308(12) 0.12305(11) 0.5236(3) 0.0280(4) Uani 1 1 d . . . . .
H22A H 0.2430(15) 0.1112(15) 0.417(3) 0.037(6) Uiso 1 1 d . . . . .
H22B H 0.1743(17) 0.1137(15) 0.514(3) 0.043(7) Uiso 1 1 d . . . . .
C23 C 0.28458(14) 0.06702(12) 0.6485(3) 0.0320(4) Uani 1 1 d . . . . .
H23A H 0.2827(15) 0.0131(17) 0.612(3) 0.042(7) Uiso 1 1 d . . . . .
H23B H 0.2614(17) 0.0686(17) 0.751(4) 0.053(8) Uiso 1 1 d . . . . .
C24 C 0.37281(13) 0.09451(12) 0.6933(3) 0.0306(4) Uani 1 1 d . . . . .
H24A H 0.3962(14) 0.0935(14) 0.593(3) 0.030(6) Uiso 1 1 d . . . . .
H24B H 0.4070(16) 0.0633(16) 0.779(3) 0.041(7) Uiso 1 1 d . . . . .
C25 C 0.38299(13) 0.17976(11) 0.7661(2) 0.0255(4) Uani 1 1 d . . . . .
H25A H 0.4326(12) 0.2000(11) 0.777(2) 0.008(4) Uiso 1 1 d . . . . .
H25B H 0.3724(14) 0.1809(14) 0.876(3) 0.033(6) Uiso 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
Cl1 C8 1.7327(17) . ?
F1 C20 1.343(2) . ?
F2 C20 1.343(2) . ?
F3 C20 1.335(2) . ?
O1 C3 1.219(2) . ?
O2 C6 1.215(2) . ?
O3 C12 1.365(2) . ?
O3 C13 1.434(2) . ?
O4 C9 1.376(2) . ?
O4 C14 1.440(2) . ?
N1 C5 1.368(2) . ?
N1 C15 1.326(2) . ?
N2 C4 1.372(2) . ?
N2 C15 1.367(2) . ?
N2 C19 1.479(2) . ?
N3 C11 1.395(2) . ?
N3 C21 1.315(2) . ?
N4 C10 1.386(2) . ?
N4 C21 1.366(2) . ?
N4 C25 1.468(2) . ?
C1 C2 1.349(2) . ?
C1 C6 1.531(2) . ?
C1 C7 1.488(2) . ?
C2 C3 1.519(2) . ?
C2 C20 1.509(2) . ?
C3 C4 1.452(2) . ?
C4 C5 1.372(2) . ?
C5 C6 1.452(2) . ?
C7 C8 1.411(2) . ?
C7 C12 1.389(2) . ?
C8 C9 1.386(2) . ?
C9 C10 1.397(2) . ?
C10 C11 1.407(2) . ?
C11 C12 1.404(2) . ?
C13 H13A 0.98(3) . ?
C13 H13B 1.00(3) . ?
C13 H13C 0.90(3) . ?
C14 H14A 0.99(2) . ?
C14 H14B 0.98(3) . ?
C14 H14C 0.98(2) . ?
C15 C16 1.496(2) . ?
C16 H16A 1.017(19) . ?
C16 H16B 0.96(3) . ?
C16 C17 1.525(3) . ?
C17 H17A 1.00(2) . ?
C17 H17B 0.96(3) . ?
C17 C18 1.516(3) . ?
C18 H18A 1.02(3) . ?
C18 H18B 0.89(3) . ?
C18 C19 1.513(3) . ?
C19 H19A 0.91(2) . ?
C19 H19B 0.98(2) . ?
C21 C22 1.501(2) . ?
C22 H22A 0.99(3) . ?
C22 H22B 0.99(3) . ?
C22 C23 1.513(3) . ?
C23 H23A 0.94(3) . ?
C23 H23B 1.05(3) . ?
C23 C24 1.515(3) . ?
C24 H24A 1.03(2) . ?
C24 H24B 0.96(3) . ?
C24 C25 1.526(3) . ?
C25 H25A 0.89(2) . ?
C25 H25B 1.00(3) . ?

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
C12 O3 C13 118.07(13) . . ?
C9 O4 C14 112.96(13) . . ?
C15 N1 C5 103.97(15) . . ?
C4 N2 C19 129.08(16) . . ?
C15 N2 C4 106.24(14) . . ?
C15 N2 C19 124.53(15) . . ?
C21 N3 C11 104.27(15) . . ?
C10 N4 C25 127.99(15) . . ?
C21 N4 C10 106.71(14) . . ?
C21 N4 C25 124.85(15) . . ?
C2 C1 C6 120.07(14) . . ?
C2 C1 C7 127.80(15) . . ?
C7 C1 C6 112.12(14) . . ?
C1 C2 C3 123.55(15) . . ?
C1 C2 C20 123.96(15) . . ?
C20 C2 C3 112.48(14) . . ?
O1 C3 C2 121.49(16) . . ?
O1 C3 C4 124.53(15) . . ?
C4 C3 C2 113.96(14) . . ?
N2 C4 C3 130.32(15) . . ?
C5 C4 N2 105.55(15) . . ?
C5 C4 C3 124.12(15) . . ?
N1 C5 C4 111.52(15) . . ?
N1 C5 C6 126.42(16) . . ?
C4 C5 C6 121.92(15) . . ?
O2 C6 C1 120.46(15) . . ?
O2 C6 C5 123.43(16) . . ?
C5 C6 C1 116.04(14) . . ?
C8 C7 C1 122.24(15) . . ?
C12 C7 C1 117.02(14) . . ?
C12 C7 C8 120.29(15) . . ?
C7 C8 Cl1 119.21(12) . . ?
C9 C8 Cl1 118.47(13) . . ?
C9 C8 C7 122.26(15) . . ?
O4 C9 C8 122.14(15) . . ?
O4 C9 C10 121.51(15) . . ?
C8 C9 C10 116.30(15) . . ?
N4 C10 C9 131.98(16) . . ?
N4 C10 C11 104.83(14) . . ?
C9 C10 C11 123.18(15) . . ?
N3 C11 C10 110.30(14) . . ?
N3 C11 C12 130.78(16) . . ?
C12 C11 C10 118.92(15) . . ?
O3 C12 C7 115.22(14) . . ?
O3 C12 C11 125.71(15) . . ?
C7 C12 C11 119.02(15) . . ?
O3 C13 H13A 106.7(15) . . ?
O3 C13 H13B 109.4(15) . . ?
O3 C13 H13C 106.7(17) . . ?
H13A C13 H13B 111(2) . . ?
H13A C13 H13C 110(2) . . ?
H13B C13 H13C 113(2) . . ?
O4 C14 H14A 106.8(13) . . ?
O4 C14 H14B 109.9(14) . . ?
O4 C14 H14C 109.3(14) . . ?
H14A C14 H14B 108.8(19) . . ?
H14A C14 H14C 111.3(18) . . ?
H14B C14 H14C 111(2) . . ?
N1 C15 N2 112.71(15) . . ?
N1 C15 C16 124.78(17) . . ?
N2 C15 C16 122.42(16) . . ?
C15 C16 H16A 102.9(10) . . ?
C15 C16 H16B 105.1(15) . . ?
C15 C16 C17 111.50(17) . . ?
H16A C16 H16B 107.1(19) . . ?
C17 C16 H16A 118.9(10) . . ?
C17 C16 H16B 110.3(15) . . ?
C16 C17 H17A 108.6(13) . . ?
C16 C17 H17B 108.9(15) . . ?
H17A C17 H17B 112.1(19) . . ?
C18 C17 C16 111.00(17) . . ?
C18 C17 H17A 108.1(13) . . ?
C18 C17 H17B 108.2(15) . . ?
C17 C18 H18A 108.7(14) . . ?
C17 C18 H18B 116.1(16) . . ?
H18A C18 H18B 110(2) . . ?
C19 C18 C17 112.14(16) . . ?
C19 C18 H18A 110.3(14) . . ?
C19 C18 H18B 99.7(16) . . ?
N2 C19 C18 108.98(16) . . ?
N2 C19 H19A 107.1(13) . . ?
N2 C19 H19B 110.6(14) . . ?
C18 C19 H19A 114.4(13) . . ?
C18 C19 H19B 111.0(14) . . ?
H19A C19 H19B 104.6(19) . . ?
F1 C20 F2 106.76(14) . . ?
F1 C20 C2 110.97(14) . . ?
F2 C20 C2 111.86(14) . . ?
F3 C20 F1 105.87(14) . . ?
F3 C20 F2 106.47(13) . . ?
F3 C20 C2 114.41(14) . . ?
N3 C21 N4 113.87(15) . . ?
N3 C21 C22 124.36(17) . . ?
N4 C21 C22 121.76(16) . . ?
C21 C22 H22A 107.8(14) . . ?
C21 C22 H22B 109.3(15) . . ?
C21 C22 C23 112.44(17) . . ?
H22A C22 H22B 107(2) . . ?
C23 C22 H22A 109.5(14) . . ?
C23 C22 H22B 110.7(15) . . ?
C22 C23 H23A 112.0(16) . . ?
C22 C23 H23B 108.0(16) . . ?
C22 C23 C24 110.82(16) . . ?
H23A C23 H23B 108(2) . . ?
C24 C23 H23A 108.4(16) . . ?
C24 C23 H23B 109.3(16) . . ?
C23 C24 H24A 110.1(13) . . ?
C23 C24 H24B 113.7(15) . . ?
C23 C24 C25 112.41(17) . . ?
H24A C24 H24B 110.1(19) . . ?
C25 C24 H24A 109.1(13) . . ?
C25 C24 H24B 101.1(15) . . ?
N4 C25 C24 109.74(16) . . ?
N4 C25 H25A 108.9(12) . . ?
N4 C25 H25B 106.3(13) . . ?
C24 C25 H25A 113.3(12) . . ?
C24 C25 H25B 112.0(13) . . ?
H25A C25 H25B 106.4(18) . . ?

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
Cl1 C8 C9 O4 -1.4(2) . . . . ?
Cl1 C8 C9 C10 175.98(13) . . . . ?
O1 C3 C4 N2 -0.9(3) . . . . ?
O1 C3 C4 C5 178.37(16) . . . . ?
O4 C9 C10 N4 -1.9(3) . . . . ?
O4 C9 C10 C11 179.30(16) . . . . ?
N1 C5 C6 O2 -5.3(3) . . . . ?
N1 C5 C6 C1 177.70(15) . . . . ?
N1 C15 C16 C17 166.42(18) . . . . ?
N2 C4 C5 N1 0.23(19) . . . . ?
N2 C4 C5 C6 -175.67(15) . . . . ?
N2 C15 C16 C17 -17.2(3) . . . . ?
N3 C11 C12 O3 -3.3(3) . . . . ?
N3 C11 C12 C7 179.19(17) . . . . ?
N3 C21 C22 C23 -163.47(18) . . . . ?
N4 C10 C11 N3 0.04(19) . . . . ?
N4 C10 C11 C12 179.86(15) . . . . ?
N4 C21 C22 C23 17.5(3) . . . . ?
C1 C2 C3 O1 179.20(16) . . . . ?
C1 C2 C3 C4 -2.3(2) . . . . ?
C1 C2 C20 F1 122.63(17) . . . . ?
C1 C2 C20 F2 -118.26(17) . . . . ?
C1 C2 C20 F3 2.9(2) . . . . ?
C1 C7 C8 Cl1 -5.5(2) . . . . ?
C1 C7 C8 C9 171.72(16) . . . . ?
C1 C7 C12 O3 11.0(2) . . . . ?
C1 C7 C12 C11 -171.21(15) . . . . ?
C2 C1 C6 O2 -172.49(16) . . . . ?
C2 C1 C6 C5 4.6(2) . . . . ?
C2 C1 C7 C8 71.2(2) . . . . ?
C2 C1 C7 C12 -116.50(19) . . . . ?
C2 C3 C4 N2 -179.32(16) . . . . ?
C2 C3 C4 C5 -0.1(2) . . . . ?
C3 C2 C20 F1 -56.10(18) . . . . ?
C3 C2 C20 F2 63.01(18) . . . . ?
C3 C2 C20 F3 -175.81(13) . . . . ?
C3 C4 C5 N1 -179.19(15) . . . . ?
C3 C4 C5 C6 4.9(3) . . . . ?
C4 N2 C15 N1 0.8(2) . . . . ?
C4 N2 C15 C16 -175.97(17) . . . . ?
C4 N2 C19 C18 161.16(17) . . . . ?
C4 C5 C6 O2 170.00(17) . . . . ?
C4 C5 C6 C1 -7.0(2) . . . . ?
C5 N1 C15 N2 -0.6(2) . . . . ?
C5 N1 C15 C16 176.03(18) . . . . ?
C6 C1 C2 C3 -0.1(2) . . . . ?
C6 C1 C2 C20 -178.67(14) . . . . ?
C6 C1 C7 C8 -107.61(18) . . . . ?
C6 C1 C7 C12 64.67(19) . . . . ?
C7 C1 C2 C3 -178.84(15) . . . . ?
C7 C1 C2 C20 2.6(3) . . . . ?
C7 C1 C6 O2 6.5(2) . . . . ?
C7 C1 C6 C5 -176.42(14) . . . . ?
C7 C8 C9 O4 -178.60(15) . . . . ?
C7 C8 C9 C10 -1.2(2) . . . . ?
C8 C7 C12 O3 -176.54(15) . . . . ?
C8 C7 C12 C11 1.2(3) . . . . ?
C8 C9 C10 N4 -179.26(17) . . . . ?
C8 C9 C10 C11 1.9(2) . . . . ?
C9 C10 C11 N3 179.15(15) . . . . ?
C9 C10 C11 C12 -1.0(3) . . . . ?
C10 N4 C21 N3 1.4(2) . . . . ?
C10 N4 C21 C22 -179.54(17) . . . . ?
C10 N4 C25 C24 -167.35(17) . . . . ?
C10 C11 C12 O3 176.93(16) . . . . ?
C10 C11 C12 C7 -0.6(3) . . . . ?
C11 N3 C21 N4 -1.3(2) . . . . ?
C11 N3 C21 C22 179.63(17) . . . . ?
C12 C7 C8 Cl1 -177.49(13) . . . . ?
C12 C7 C8 C9 -0.3(3) . . . . ?
C13 O3 C12 C7 -156.34(17) . . . . ?
C13 O3 C12 C11 26.1(3) . . . . ?
C14 O4 C9 C8 -85.1(2) . . . . ?
C14 O4 C9 C10 97.64(19) . . . . ?
C15 N1 C5 C4 0.2(2) . . . . ?
C15 N1 C5 C6 175.90(16) . . . . ?
C15 N2 C4 C3 178.79(17) . . . . ?
C15 N2 C4 C5 -0.58(18) . . . . ?
C15 N2 C19 C18 -23.9(2) . . . . ?
C15 C16 C17 C18 43.0(2) . . . . ?
C16 C17 C18 C19 -62.5(2) . . . . ?
C17 C18 C19 N2 50.2(2) . . . . ?
C19 N2 C4 C3 -5.6(3) . . . . ?
C19 N2 C4 C5 175.07(16) . . . . ?
C19 N2 C15 N1 -175.12(16) . . . . ?
C19 N2 C15 C16 8.1(3) . . . . ?
C20 C2 C3 O1 -2.1(2) . . . . ?
C20 C2 C3 C4 176.41(14) . . . . ?
C21 N3 C11 C10 0.7(2) . . . . ?
C21 N3 C11 C12 -179.05(19) . . . . ?
C21 N4 C10 C9 -179.77(18) . . . . ?
C21 N4 C10 C11 -0.78(18) . . . . ?
C21 N4 C25 C24 21.5(3) . . . . ?
C21 C22 C23 C24 -43.4(2) . . . . ?
C22 C23 C24 C25 61.0(2) . . . . ?
C23 C24 C25 N4 -47.9(2) . . . . ?
C25 N4 C10 C9 7.8(3) . . . . ?
C25 N4 C10 C11 -173.23(17) . . . . ?
C25 N4 C21 N3 174.11(16) . . . . ?
C25 N4 C21 C22 -6.8(3) . . . . ?

_olex2_date_sample_data_collection 2020-02-11
_olex2_exptl_crystal_mounting_method 
'Crystal cut from large lump and mounted on a Hampton Research 20um nyloon loop (0.3mm diameter) and cooled from 295K to 100K'
_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 1.283
_oxdiff_exptl_absorpt_empirical_full_min 0.841
####################################################################### 
# 
# 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_exp_2189
_database_code_depnum_ccdc_archive 'CCDC 2022191'
loop_
_audit_author_name
_audit_author_address
'Jeremy Karl Cockcroft'
;University College London
United Kingdom
;
_audit_update_record             
;
2020-08-07 deposited with the CCDC.	2021-02-26 downloaded from the CCDC.
;
_audit_creation_date             2020-07-15
_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        
7''-bromo-5'',8''-dimethoxy-[6,6''-bipyrrolo[1,2-a]benzimidazole]-5,8-dione
_chemical_formula_moiety         'C22 H19 Br N4 O4'
_chemical_formula_sum            'C22 H19 Br N4 O4'
_chemical_formula_weight         483.32
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C22 H20 Br N4 O4'
_chemical_oxdiff_usercomment     'Darren Conboy 199D'
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                   23.3635(2)
_cell_length_b                   9.58790(10)
_cell_length_c                   17.6817(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3960.82(7)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    48903
_cell_measurement_temperature    150
_cell_measurement_theta_max      72.4470
_cell_measurement_theta_min      4.4850
_shelx_estimated_absorpt_T_max   0.595
_shelx_estimated_absorpt_T_min   0.353
_exptl_absorpt_coefficient_mu    3.171
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.245
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.76a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear orangish red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   orangish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.621
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1968
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
7 -2 -9 0.1888
-7 -5 4 0.0907
4 6 0 0.0628
-7 2 9 0.1557
13 -3 -3 0.1239
10 -2 8 0.1490
-11 2 -7 0.1613
-10 -3 -7 0.1732
-14 0 4 0.1241
-13 -3 2 0.0939
-3 -6 4 0.1005
2 -6 4 0.1016
-4 6 -1 0.0524
-3 4 -8 0.1467
7 -5 4 0.1062
5 -4 7 0.1094
-5 2 -10 0.1693
11 -4 -2 0.1194
12 1 7 0.1512
0 6 -1 0.0386

_exptl_crystal_size_max          0.415
_exptl_crystal_size_mid          0.271
_exptl_crystal_size_min          0.183
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
6.9562 -2.2754 -9.2959 0.0502 -0.0485 -0.9976
-7.2457 -4.9504 4.2953 0.6694 -0.6807 0.2976
4.3686 5.9561 -0.4030 -0.6965 0.7072 0.1215
-7.3518 1.8688 9.4300 -0.0002 -0.0023 1.0000
12.9597 -2.6294 -3.4650 0.4737 0.3931 -0.7881
10.4136 -1.5796 7.8163 0.7623 0.6291 0.1519
-10.8673 1.6878 -7.3729 -0.7673 -0.6334 -0.1004
-9.5209 -2.6978 -7.4050 -0.1700 -0.9179 -0.3586
-14.2951 -0.1647 3.8215 -0.1244 -0.6823 0.7204
-13.2138 -2.8881 1.8257 0.1677 -0.8962 0.4107
-2.8371 -5.7451 3.8751 0.8498 -0.5196 0.0887
1.9100 -5.7066 4.3645 0.9680 -0.2495 -0.0254
-4.1901 5.9595 -0.9752 -0.9059 0.2341 0.3529
-3.4163 3.9737 -8.4579 -0.9496 -0.0761 -0.3041
7.0309 -5.0152 4.2409 0.9835 0.0779 -0.1635
4.8308 -4.4597 7.1340 0.9869 0.0788 0.1407
-4.6017 2.4653 -9.9526 -0.8428 -0.3001 -0.4467
11.4003 -3.9697 -1.9195 0.6799 0.2401 -0.6929
11.9521 0.8502 6.8756 0.4399 0.8848 0.1536
0.2078 6.1870 -1.2607 -0.8527 0.4811 0.2036

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0494
_diffrn_reflns_av_unetI/netI     0.0130
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            68493
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.775
_diffrn_reflns_theta_min         3.784
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2031
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -4.00  21.00   1.00    1.00    --   34.00  93.00  66.76   25
  2  ω     -5.00  20.00   1.00    1.00    --   34.00  94.00-159.89   25
  3  ω     -4.00  21.00   1.00    1.00    --   34.00  93.00 -52.81   25
  4  ω      8.00  33.00   1.00    1.00    --   42.00  83.00  40.12   25
  5  ω      8.00  34.00   1.00    1.00    --   42.00  83.00 160.87   26
  6  ω    -86.00 -15.00   1.00    1.00    --  -42.62 125.00 -90.00   71
  7  ω   -115.00 -18.00   1.00    1.00    --  -42.62 -38.00   0.00   97
  8  ω   -116.00 -18.00   1.00    1.00    --  -42.62 -38.00-180.00   98
  9  ω    -74.00  34.00   1.00    1.00    --  -42.62  83.00 128.00  108
 10  ω   -112.00 -28.00   1.00    1.00    --  -42.62 -38.00  90.00   84
 11  ω     14.00  41.00   1.00    1.00    --   46.00  79.00 -92.49   27
 12  ω     14.00  42.00   1.00    1.00    --   46.00  77.00-179.01   28
 13  ω     26.00  52.00   1.00    1.00    --   58.00  74.00 -46.52   26
 14  ω     30.00  56.00   1.00    1.00    --   62.00  74.00  98.81   26
 15  ω     30.00  56.00   1.00    1.00    --   62.00  74.00  69.01   26
 16  ω     31.00  57.00   1.00    1.00    --   62.00  72.00 -98.93   26
 17  ω     71.00  98.00   1.00    1.00    --   62.00  72.00 -98.93   27
 18  ω     30.00  59.00   1.00    1.00    --   62.00  73.00-143.88   29
 19  ω     34.00  66.00   1.00    1.00    --   66.00  73.00 -38.41   32
 20  ω     36.00  61.00   1.00    1.00    --   66.00  69.00 137.11   25
 21  ω    109.00 145.00   1.00    1.00    --   70.00  74.00  20.43   36
 22  ω     39.00  65.00   1.00    1.00    --   70.00  72.00 -19.60   26
 23  ω     39.00  65.00   1.00    1.00    --   70.00  72.00 147.97   26
 24  ω     38.00  75.00   1.00    1.00    --   70.00  74.00  20.43   37
 25  ω    111.00 146.00   1.00    1.00    --   74.00  67.00-179.52   35
 26  ω     45.00  76.00   1.00    1.00    --   74.00  67.00-179.52   31
 27  ω     46.00  76.00   1.00    1.00    --   78.00  74.00 147.29   30
 28  ω     48.00  74.00   1.00    1.00    --   78.00  67.00  91.25   26
 29  ω     49.00  76.00   1.00    1.00    --   78.00  63.00 -75.55   27
 30  ω     50.00  76.00   1.00    1.00    --   82.00  73.00 -53.40   26
 31  ω     54.00  80.00   1.00    1.00    --   86.00  73.00 -20.77   26
 32  ω     55.00  85.00   1.00    1.00    --   86.00  72.00   6.56   30
 33  ω    135.00 161.00   1.00    1.00    --   86.00  73.00 -20.77   26
 34  ω     58.00  84.00   1.00    1.00    --   90.00  73.00  45.78   26
 35  ω     59.00  85.00   1.00    1.00    --   90.00  71.00 -39.12   26
 36  ω     61.00  96.00   1.00    1.00    --   90.00  59.00 -91.15   35
 37  ω     59.00  89.00   1.00    1.00    --   90.00  70.00-139.52   30
 38  ω     97.00 162.00   1.00    1.00    --   94.00  72.00  95.16   65
 39  ω     63.00  89.00   1.00    1.00    --   94.00  72.00  95.16   26
 40  ω    109.00 166.00   1.00    1.00    --   94.00  68.00 129.10   57
 41  ω     64.00  90.00   1.00    1.00    --   94.00  68.00 129.10   26
 42  ω     71.00 172.00   1.00    1.00    --  102.00  71.00  67.06  101
 43  ω     74.00 164.00   1.00    1.00    --  104.49  72.00  -1.90   90
 44  ω     76.00 102.00   1.00    1.00    --  104.49  61.00 -90.00   26
 45  ω    141.00 172.00   1.00    1.00    --  104.49  63.00 -66.65   31
 46  ω     30.00 106.00   1.00    1.00    --  104.49 -94.00  90.00   76
 47  ω     76.00 131.00   1.00    1.00    --  104.49  63.00 -66.65   55
 48  ω     75.00 107.00   1.00    1.00    --  104.49  61.00-180.00   32
 49  ω     32.00 106.00   1.00    1.00    --  104.49 -97.00 -65.26   74
 50  ω    107.00 134.00   1.00    1.00    --  104.49 -61.00 120.00   27
 51  ω     32.00  98.00   1.00    1.00    --  104.49 -61.00 120.00   66
 52  ω     75.00 176.00   1.00    1.00    --  104.49  61.00-120.00  101
 53  ω    121.00 177.00   1.00    1.00    --  104.49  61.00 150.00   56
 54  ω     75.00 103.00   1.00    1.00    --  104.49  61.00 150.00   28
 55  ω     32.00 117.00   1.00    1.00    --  104.49 -61.00 -60.00   85
 56  ω     52.00 106.00   1.00    1.00    --  104.49 -94.00-150.00   54
 57  ω     76.00 176.00   1.00    1.00    --  104.49  61.00-170.16  100
 58  ω     75.00 172.00   1.00    1.00    --  104.49  61.00 -30.00   97
 59  ω     72.00 103.00   1.00    1.00    --  104.49 -94.00  30.00   31
 60  ω     81.00 106.00   1.00    1.00    --  104.49 -94.00 120.00   25
 61  ω    136.00 170.00   1.00    1.00    --  104.49  61.00 -90.00   34
 62  ω     28.00  53.00   1.00    1.00    --  104.49 -94.00 120.00   25
 63  ω     75.00 161.00   1.00    1.00    --  104.49  72.00  32.06   86
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0215741000
_diffrn_orient_matrix_UB_12      -0.1298782000
_diffrn_orient_matrix_UB_13      0.0425400000
_diffrn_orient_matrix_UB_21      0.0536055000
_diffrn_orient_matrix_UB_22      0.0811453000
_diffrn_orient_matrix_UB_23      0.0254689000
_diffrn_orient_matrix_UB_31      -0.0318061000
_diffrn_orient_matrix_UB_32      0.0485752000
_diffrn_orient_matrix_UB_33      0.0716213000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3865
_reflns_number_total             3921
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_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 1.171.40.76a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.76a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.76a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.795
_refine_diff_density_min         -0.834
_refine_diff_density_rms         0.080
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.153
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     351
_refine_ls_number_reflns         3921
_refine_ls_number_restraints     76
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0431
_refine_ls_restrained_S_all      1.149
_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)+(0.0488P)²+9.0343P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1161
_refine_ls_wR_factor_ref         0.1163
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C14-H14A \\sim C14-H14B \\sim C14-H14C
 with sigma of 0.001
 C16-H16A \\sim C16-H16B \\sim C17-H17A \\sim C17-H17B \\sim C18-H18A \\sim
C18-H18B \\sim C20-H20A ~
 C20-H20B \\sim C21-H21A \\sim C21-H21B \\sim C22-H22A \\sim C22-H22B
 with sigma of 0.001
3. Rigid bond restraints
 O3, O3, C13A, C13B
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
4. Uiso/Uaniso restraints and constraints
C13A \\sim C13B: within 2A with sigma of 0.001 and sigma for terminal atoms of
0.002
5. Others
 Sof(C13B)=Sof(H13D)=Sof(H13E)=Sof(H13F)=1-FVAR(1)
 Sof(C13A)=Sof(H13A)=Sof(H13B)=Sof(H13C)=FVAR(1)
6.a Idealised Me refined as rotating group:
 C13A(H13A,H13B,H13C), C13B(H13D,H13E,H13F)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.27273(2) 0.52550(4) 0.66969(2) 0.03154(13) Uani 1 1 d . . . . .
O1 O 0.46763(9) 0.4686(2) 0.86109(12) 0.0267(5) Uani 1 1 d . . . . .
O2 O 0.32815(12) 0.8558(3) 0.73822(13) 0.0426(6) Uani 1 1 d . . . . .
O3 O 0.46903(9) 0.7741(2) 0.62195(12) 0.0266(4) Uani 1 1 d . U . . .
O4 O 0.26101(8) 0.5911(2) 0.50087(12) 0.0252(4) Uani 1 1 d . . . . .
N1 N 0.34869(11) 0.8480(3) 0.90352(14) 0.0267(5) Uani 1 1 d . . . . .
N2 N 0.40665(10) 0.6877(3) 0.95427(13) 0.0206(5) Uani 1 1 d . . . . .
N3 N 0.43543(11) 0.8167(3) 0.45548(14) 0.0237(5) Uani 1 1 d . . . . .
N4 N 0.35256(10) 0.7319(2) 0.41078(13) 0.0210(5) Uani 1 1 d . . . . .
C1 C 0.38899(12) 0.6595(3) 0.72021(15) 0.0204(6) Uani 1 1 d . . . . .
C2 C 0.42416(12) 0.5663(3) 0.75179(16) 0.0216(6) Uani 1 1 d . . . . .
H2 H 0.4362(15) 0.501(4) 0.727(2) 0.021(9) Uiso 1 1 d . . . . .
C3 C 0.43588(12) 0.5566(3) 0.83439(16) 0.0210(6) Uani 1 1 d . . . . .
C4 C 0.40549(11) 0.6604(3) 0.87853(16) 0.0200(5) Uani 1 1 d . . . . .
C5 C 0.36960(12) 0.7600(3) 0.84917(16) 0.0223(6) Uani 1 1 d . . . . .
C6 C 0.35838(12) 0.7683(3) 0.76756(16) 0.0241(6) Uani 1 1 d . . . . .
C7 C 0.37808(12) 0.6686(3) 0.63744(15) 0.0193(5) Uani 1 1 d . . . . .
C8 C 0.32665(12) 0.6167(3) 0.60654(16) 0.0215(6) Uani 1 1 d . . . . .
C9 C 0.31275(12) 0.6302(3) 0.53078(16) 0.0204(5) Uani 1 1 d . . . . .
C10 C 0.35293(12) 0.6995(3) 0.48622(15) 0.0199(5) Uani 1 1 d . . . . .
C11 C 0.40484(12) 0.7529(3) 0.51362(16) 0.0203(5) Uani 1 1 d . . . . .
C12 C 0.41766(12) 0.7358(3) 0.59085(16) 0.0206(6) Uani 1 1 d . . . . .
C13A C 0.48714(16) 0.9126(4) 0.6099(2) 0.0222(7) Uani 0.725(6) 1 d . U P A 1
H13A H 0.4851 0.9344 0.5558 0.033 Uiso 0.725(6) 1 calc GR . P A 1
H13B H 0.5267 0.9233 0.6275 0.033 Uiso 0.725(6) 1 calc GR . P A 1
H13C H 0.4622 0.9764 0.6380 0.033 Uiso 0.725(6) 1 calc GR . P A 1
C13B C 0.4622(4) 0.9026(10) 0.6637(5) 0.0189(11) Uiso 0.275(6) 1 d . U P A 2
H13D H 0.4244 0.9424 0.6530 0.028 Uiso 0.275(6) 1 calc GR . P A 2
H13E H 0.4919 0.9689 0.6483 0.028 Uiso 0.275(6) 1 calc GR . P A 2
H13F H 0.4656 0.8838 0.7179 0.028 Uiso 0.275(6) 1 calc GR . P A 2
C14 C 0.25911(15) 0.4505(4) 0.4723(2) 0.0374(8) Uani 1 1 d D . . . .
H14A H 0.2675(17) 0.386(3) 0.5155(14) 0.052(13) Uiso 1 1 d D . . . .
H14B H 0.2203(9) 0.440(5) 0.448(2) 0.055(13) Uiso 1 1 d D . . . .
H14C H 0.2909(11) 0.434(5) 0.4352(16) 0.052(12) Uiso 1 1 d D . . . .
C15 C 0.37258(12) 0.7991(3) 0.96644(17) 0.0236(6) Uani 1 1 d . . . . .
C16 C 0.37170(15) 0.8380(4) 1.04795(19) 0.0341(7) Uani 1 1 d D . . . .
H16A H 0.3858(17) 0.9323(17) 1.052(3) 0.070(15) Uiso 1 1 d D . . . .
H16B H 0.3326(6) 0.829(5) 1.065(2) 0.049(12) Uiso 1 1 d D . . . .
C17 C 0.41101(18) 0.7283(4) 1.08398(18) 0.0376(8) Uani 1 1 d D . . . .
H17A H 0.4418(10) 0.774(4) 1.1107(18) 0.060(14) Uiso 1 1 d D . . . .
H17B H 0.3873(13) 0.662(3) 1.111(2) 0.080(17) Uiso 1 1 d D . . . .
C18 C 0.43612(13) 0.6350(3) 1.02205(16) 0.0248(6) Uani 1 1 d D . . . .
H18A H 0.4762(5) 0.656(4) 1.015(2) 0.041(11) Uiso 1 1 d D . . . .
H18B H 0.4270(17) 0.5372(13) 1.027(2) 0.046(12) Uiso 1 1 d D . . . .
C19 C 0.40255(12) 0.8003(3) 0.39612(17) 0.0237(6) Uani 1 1 d . . . . .
C20 C 0.40586(15) 0.8361(4) 0.31413(18) 0.0321(7) Uani 1 1 d D . . . .
H20A H 0.4183(15) 0.9303(15) 0.304(2) 0.039(10) Uiso 1 1 d D . . . .
H20B H 0.4372(10) 0.786(3) 0.2914(19) 0.053(12) Uiso 1 1 d D . . . .
C21 C 0.34519(19) 0.8014(5) 0.2860(2) 0.0481(10) Uani 1 1 d D . . . .
H21A H 0.344(2) 0.764(4) 0.2354(9) 0.065(15) Uiso 1 1 d D . . . .
H21B H 0.3219(15) 0.882(3) 0.275(4) 0.14(3) Uiso 1 1 d D . . . .
C22 C 0.31697(15) 0.7067(4) 0.34395(18) 0.0315(7) Uani 1 1 d D . . . .
H22A H 0.2770(5) 0.726(4) 0.352(2) 0.030(9) Uiso 1 1 d D . . . .
H22B H 0.3119(17) 0.6081(11) 0.335(2) 0.036(10) Uiso 1 1 d 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 C8 1.897(3) . ?
O1 C3 1.218(4) . ?
O2 C6 1.213(4) . ?
O3 C12 1.370(3) . ?
O3 C13A 1.410(4) . ?
O3 C13B 1.445(10) . ?
O4 C9 1.372(3) . ?
O4 C14 1.441(4) . ?
N1 C5 1.369(4) . ?
N1 C15 1.330(4) . ?
N2 C4 1.365(4) . ?
N2 C15 1.349(4) . ?
N2 C18 1.472(4) . ?
N3 C11 1.394(4) . ?
N3 C19 1.310(4) . ?
N4 C10 1.370(4) . ?
N4 C19 1.365(4) . ?
N4 C22 1.465(4) . ?
C1 C2 1.336(4) . ?
C1 C6 1.517(4) . ?
C1 C7 1.488(4) . ?
C2 H2 0.82(4) . ?
C2 C3 1.489(4) . ?
C3 C4 1.451(4) . ?
C4 C5 1.373(4) . ?
C5 C6 1.469(4) . ?
C7 C8 1.411(4) . ?
C7 C12 1.396(4) . ?
C8 C9 1.385(4) . ?
C9 C10 1.394(4) . ?
C10 C11 1.403(4) . ?
C11 C12 1.407(4) . ?
C13A H13A 0.9800 . ?
C13A H13B 0.9800 . ?
C13A H13C 0.9800 . ?
C13B H13D 0.9800 . ?
C13B H13E 0.9800 . ?
C13B H13F 0.9800 . ?
C14 H14A 1.004(18) . ?
C14 H14B 1.004(18) . ?
C14 H14C 1.004(18) . ?
C15 C16 1.489(4) . ?
C16 H16A 0.965(8) . ?
C16 H16B 0.965(8) . ?
C16 C17 1.535(5) . ?
C17 H17A 0.965(8) . ?
C17 H17B 0.965(8) . ?
C17 C18 1.531(4) . ?
C18 H18A 0.965(8) . ?
C18 H18B 0.965(8) . ?
C19 C20 1.492(4) . ?
C20 H20A 0.965(8) . ?
C20 H20B 0.965(8) . ?
C20 C21 1.538(5) . ?
C21 H21A 0.965(8) . ?
C21 H21B 0.965(8) . ?
C21 C22 1.519(5) . ?
C22 H22A 0.965(8) . ?
C22 H22B 0.965(8) . ?

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
C12 O3 C13A 117.0(2) . . ?
C12 O3 C13B 109.7(4) . . ?
C9 O4 C14 114.7(2) . . ?
C15 N1 C5 102.7(2) . . ?
C4 N2 C18 137.9(3) . . ?
C15 N2 C4 107.2(2) . . ?
C15 N2 C18 114.7(2) . . ?
C19 N3 C11 103.8(2) . . ?
C10 N4 C22 138.8(3) . . ?
C19 N4 C10 106.8(2) . . ?
C19 N4 C22 114.3(2) . . ?
C2 C1 C6 121.3(3) . . ?
C2 C1 C7 123.8(3) . . ?
C7 C1 C6 114.9(2) . . ?
C1 C2 H2 120(3) . . ?
C1 C2 C3 124.4(3) . . ?
C3 C2 H2 114(3) . . ?
O1 C3 C2 122.4(3) . . ?
O1 C3 C4 124.4(3) . . ?
C4 C3 C2 113.2(2) . . ?
N2 C4 C3 130.5(3) . . ?
N2 C4 C5 104.5(2) . . ?
C5 C4 C3 125.0(3) . . ?
N1 C5 C4 112.4(3) . . ?
N1 C5 C6 126.3(3) . . ?
C4 C5 C6 121.2(3) . . ?
O2 C6 C1 120.9(3) . . ?
O2 C6 C5 124.2(3) . . ?
C5 C6 C1 114.9(2) . . ?
C8 C7 C1 120.4(2) . . ?
C12 C7 C1 119.6(2) . . ?
C12 C7 C8 119.9(2) . . ?
C7 C8 Br1 120.0(2) . . ?
C9 C8 Br1 117.2(2) . . ?
C9 C8 C7 122.8(3) . . ?
O4 C9 C8 123.6(3) . . ?
O4 C9 C10 120.4(2) . . ?
C8 C9 C10 115.7(3) . . ?
N4 C10 C9 130.9(3) . . ?
N4 C10 C11 105.0(2) . . ?
C9 C10 C11 124.1(3) . . ?
N3 C11 C10 110.4(2) . . ?
N3 C11 C12 131.1(3) . . ?
C10 C11 C12 118.5(3) . . ?
O3 C12 C7 117.8(2) . . ?
O3 C12 C11 123.0(3) . . ?
C7 C12 C11 119.0(3) . . ?
O3 C13A H13A 109.5 . . ?
O3 C13A H13B 109.5 . . ?
O3 C13A H13C 109.5 . . ?
H13A C13A H13B 109.5 . . ?
H13A C13A H13C 109.5 . . ?
H13B C13A H13C 109.5 . . ?
O3 C13B H13D 109.5 . . ?
O3 C13B H13E 109.5 . . ?
O3 C13B H13F 109.5 . . ?
H13D C13B H13E 109.5 . . ?
H13D C13B H13F 109.5 . . ?
H13E C13B H13F 109.5 . . ?
O4 C14 H14A 108(2) . . ?
O4 C14 H14B 106(3) . . ?
O4 C14 H14C 111(3) . . ?
H14A C14 H14B 116(3) . . ?
H14A C14 H14C 105(3) . . ?
H14B C14 H14C 112(3) . . ?
N1 C15 N2 113.2(3) . . ?
N1 C15 C16 135.7(3) . . ?
N2 C15 C16 111.1(3) . . ?
C15 C16 H16A 108(3) . . ?
C15 C16 H16B 107(2) . . ?
C15 C16 C17 102.8(3) . . ?
H16A C16 H16B 113(4) . . ?
C17 C16 H16A 114(3) . . ?
C17 C16 H16B 112(2) . . ?
C16 C17 H17A 110(2) . . ?
C16 C17 H17B 108(2) . . ?
H17A C17 H17B 119(3) . . ?
C18 C17 C16 109.4(3) . . ?
C18 C17 H17A 109(2) . . ?
C18 C17 H17B 101(2) . . ?
N2 C18 C17 101.7(2) . . ?
N2 C18 H18A 106(2) . . ?
N2 C18 H18B 108(3) . . ?
C17 C18 H18A 110(2) . . ?
C17 C18 H18B 115(3) . . ?
H18A C18 H18B 115(3) . . ?
N3 C19 N4 114.0(3) . . ?
N3 C19 C20 136.1(3) . . ?
N4 C19 C20 109.9(3) . . ?
C19 C20 H20A 114(2) . . ?
C19 C20 H20B 109(2) . . ?
C19 C20 C21 102.5(3) . . ?
H20A C20 H20B 99(3) . . ?
C21 C20 H20A 115(2) . . ?
C21 C20 H20B 117(2) . . ?
C20 C21 H21A 113(3) . . ?
C20 C21 H21B 114(2) . . ?
H21A C21 H21B 96(4) . . ?
C22 C21 C20 108.1(3) . . ?
C22 C21 H21A 113(2) . . ?
C22 C21 H21B 112(3) . . ?
N4 C22 C21 101.5(3) . . ?
N4 C22 H22A 113(2) . . ?
N4 C22 H22B 111(2) . . ?
C21 C22 H22A 114(2) . . ?
C21 C22 H22B 122(2) . . ?
H22A C22 H22B 96(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
Br1 C8 C9 O4 5.0(4) . . . . ?
Br1 C8 C9 C10 179.1(2) . . . . ?
O1 C3 C4 N2 3.1(5) . . . . ?
O1 C3 C4 C5 -180.0(3) . . . . ?
O4 C9 C10 N4 -4.9(5) . . . . ?
O4 C9 C10 C11 174.7(3) . . . . ?
N1 C5 C6 O2 -0.6(5) . . . . ?
N1 C5 C6 C1 178.0(3) . . . . ?
N1 C15 C16 C17 -179.9(4) . . . . ?
N2 C4 C5 N1 0.2(3) . . . . ?
N2 C4 C5 C6 178.2(3) . . . . ?
N2 C15 C16 C17 -0.8(4) . . . . ?
N3 C11 C12 O3 -5.6(5) . . . . ?
N3 C11 C12 C7 178.8(3) . . . . ?
N3 C19 C20 C21 -171.2(4) . . . . ?
N4 C10 C11 N3 0.0(3) . . . . ?
N4 C10 C11 C12 179.8(2) . . . . ?
N4 C19 C20 C21 9.8(4) . . . . ?
C1 C2 C3 O1 178.9(3) . . . . ?
C1 C2 C3 C4 -0.6(4) . . . . ?
C1 C7 C8 Br1 -3.4(4) . . . . ?
C1 C7 C8 C9 175.9(3) . . . . ?
C1 C7 C12 O3 8.8(4) . . . . ?
C1 C7 C12 C11 -175.3(3) . . . . ?
C2 C1 C6 O2 177.3(3) . . . . ?
C2 C1 C6 C5 -1.3(4) . . . . ?
C2 C1 C7 C8 103.6(3) . . . . ?
C2 C1 C7 C12 -79.9(4) . . . . ?
C2 C3 C4 N2 -177.4(3) . . . . ?
C2 C3 C4 C5 -0.5(4) . . . . ?
C3 C4 C5 N1 -177.3(3) . . . . ?
C3 C4 C5 C6 0.6(4) . . . . ?
C4 N2 C15 N1 0.0(3) . . . . ?
C4 N2 C15 C16 -179.3(3) . . . . ?
C4 N2 C18 C17 179.9(3) . . . . ?
C4 C5 C6 O2 -178.3(3) . . . . ?
C4 C5 C6 C1 0.3(4) . . . . ?
C5 N1 C15 N2 0.1(3) . . . . ?
C5 N1 C15 C16 179.2(4) . . . . ?
C6 C1 C2 C3 1.5(4) . . . . ?
C6 C1 C7 C8 -78.3(3) . . . . ?
C6 C1 C7 C12 98.2(3) . . . . ?
C7 C1 C2 C3 179.5(3) . . . . ?
C7 C1 C6 O2 -0.9(4) . . . . ?
C7 C1 C6 C5 -179.5(2) . . . . ?
C7 C8 C9 O4 -174.3(3) . . . . ?
C7 C8 C9 C10 -0.2(4) . . . . ?
C8 C7 C12 O3 -174.6(2) . . . . ?
C8 C7 C12 C11 1.2(4) . . . . ?
C8 C9 C10 N4 -179.2(3) . . . . ?
C8 C9 C10 C11 0.4(4) . . . . ?
C9 C10 C11 N3 -179.7(3) . . . . ?
C9 C10 C11 C12 0.1(4) . . . . ?
C10 N4 C19 N3 -0.6(3) . . . . ?
C10 N4 C19 C20 178.6(2) . . . . ?
C10 N4 C22 C21 171.9(4) . . . . ?
C10 C11 C12 O3 174.7(3) . . . . ?
C10 C11 C12 C7 -1.0(4) . . . . ?
C11 N3 C19 N4 0.6(3) . . . . ?
C11 N3 C19 C20 -178.4(4) . . . . ?
C12 C7 C8 Br1 -179.9(2) . . . . ?
C12 C7 C8 C9 -0.6(4) . . . . ?
C13A O3 C12 C7 -130.4(3) . . . . ?
C13A O3 C12 C11 53.9(4) . . . . ?
C13B O3 C12 C7 -80.5(5) . . . . ?
C13B O3 C12 C11 103.9(5) . . . . ?
C14 O4 C9 C8 -92.1(4) . . . . ?
C14 O4 C9 C10 94.1(3) . . . . ?
C15 N1 C5 C4 -0.2(3) . . . . ?
C15 N1 C5 C6 -178.1(3) . . . . ?
C15 N2 C4 C3 177.2(3) . . . . ?
C15 N2 C4 C5 -0.1(3) . . . . ?
C15 N2 C18 C17 4.1(3) . . . . ?
C15 C16 C17 C18 3.3(4) . . . . ?
C16 C17 C18 N2 -4.4(4) . . . . ?
C18 N2 C4 C3 1.2(5) . . . . ?
C18 N2 C4 C5 -176.2(3) . . . . ?
C18 N2 C15 N1 177.1(2) . . . . ?
C18 N2 C15 C16 -2.2(4) . . . . ?
C19 N3 C11 C10 -0.3(3) . . . . ?
C19 N3 C11 C12 179.9(3) . . . . ?
C19 N4 C10 C9 180.0(3) . . . . ?
C19 N4 C10 C11 0.3(3) . . . . ?
C19 N4 C22 C21 -13.3(4) . . . . ?
C19 C20 C21 C22 -18.0(4) . . . . ?
C20 C21 C22 N4 18.9(4) . . . . ?
C22 N4 C10 C9 -5.0(6) . . . . ?
C22 N4 C10 C11 175.3(3) . . . . ?
C22 N4 C19 N3 -177.0(3) . . . . ?
C22 N4 C19 C20 2.3(4) . . . . ?

_olex2_date_sample_data_collection 2020-02-24
_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 1.513
_oxdiff_exptl_absorpt_empirical_full_min 0.808
