# 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_EH_83_a
_database_code_depnum_ccdc_archive 'CCDC 2177685'
loop_
_audit_author_name
_audit_author_address
'Huiyeung Ju'
;Yeungnam University
South Korea
;
_audit_update_record             
;
2022-06-08 deposited with the CCDC.	2022-08-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
3-(9-(Pyridin-2-yl)-9H-carbazol-1-yl)-1-(2,4,6-trichlorophenyl)pyrrolidine-2,5-dione
_chemical_name_common            ?
_chemical_melting_point          399
_chemical_formula_moiety         '2(C27 H16 Cl3 N3 O2), C3 H6 O'
_chemical_formula_sum            'C57 H38 Cl6 N6 O5'
_chemical_formula_weight         1099.63

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   31.146(18)
_cell_length_b                   11.338(7)
_cell_length_c                   15.115(9)
_cell_angle_alpha                90
_cell_angle_beta                 95.043(19)
_cell_angle_gamma                90
_cell_volume                     5317(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    8155
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      24.01

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_F_000             2256
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.042
_exptl_absorpt_coefficient_mu    0.378
_shelx_estimated_absorpt_T_min   0.921
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6814
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            48713
_diffrn_reflns_av_unetI/netI     0.0592
_diffrn_reflns_av_R_equivalents  0.0883
_diffrn_reflns_limit_h_min       -41
_diffrn_reflns_limit_h_max       41
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.912
_diffrn_reflns_theta_max         28.522
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6666
_reflns_number_gt                3859
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1673P)²+7.9730P] 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         6666
_refine_ls_number_parameters     335
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.1378
_refine_ls_R_factor_gt           0.0814
_refine_ls_wR_factor_ref         0.2937
_refine_ls_wR_factor_gt          0.2405
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.059
_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 0.22413(4) 0.32279(10) 0.35717(7) 0.0535(3) Uani 1 1 d . . . . .
Cl2 Cl 0.26323(4) 0.61912(10) 0.63275(7) 0.0547(3) Uani 1 1 d . . . . .
Cl3 Cl 0.14640(5) 0.27598(15) 0.65807(10) 0.0787(5) Uani 1 1 d . . . . .
O1 O 0.33190(9) 0.4536(3) 0.5401(2) 0.0517(8) Uani 1 1 d . . . . .
O2 O 0.22783(9) 0.6078(3) 0.3426(2) 0.0489(7) Uani 1 1 d . . . . .
O3 O 0.500000 0.0811(9) 0.250000 0.183(4) Uani 1 2 d S TU P . .
N1 N 0.27312(10) 0.5201(3) 0.4518(2) 0.0375(7) Uani 1 1 d . . . . .
N2 N 0.44265(10) 0.6224(3) 0.4075(2) 0.0404(8) Uani 1 1 d . . . . .
N3 N 0.40718(11) 0.5613(4) 0.2733(2) 0.0499(9) Uani 1 1 d . . . . .
C1 C 0.24106(11) 0.4650(3) 0.4996(2) 0.0367(8) Uani 1 1 d . . . . .
C2 C 0.21588(12) 0.3725(4) 0.4629(3) 0.0400(9) Uani 1 1 d . . . . .
C3 C 0.18585(14) 0.3166(4) 0.5086(3) 0.0495(10) Uani 1 1 d . . . . .
H3 H 0.168634 0.255822 0.482269 0.059 Uiso 1 1 calc R U . . .
C4 C 0.18154(14) 0.3524(4) 0.5953(3) 0.0508(11) Uani 1 1 d . . . . .
C5 C 0.20490(13) 0.4449(4) 0.6347(3) 0.0489(10) Uani 1 1 d . . . . .
H5 H 0.201031 0.468799 0.692993 0.059 Uiso 1 1 calc R U . . .
C6 C 0.23427(13) 0.5014(4) 0.5853(3) 0.0414(9) Uani 1 1 d . . . . .
C7 C 0.31716(12) 0.5091(3) 0.4762(3) 0.0394(8) Uani 1 1 d . . . . .
C8 C 0.34137(12) 0.5742(4) 0.4086(3) 0.0425(9) Uani 1 1 d . . . . .
H8 H 0.361104 0.518477 0.382108 0.051 Uiso 1 1 calc R U . . .
C9 C 0.30611(14) 0.6130(4) 0.3367(3) 0.0525(11) Uani 1 1 d . . . . .
H9A H 0.308092 0.697834 0.325384 0.063 Uiso 1 1 calc R U . . .
H9AB H 0.309021 0.570520 0.281038 0.063 Uiso 1 1 calc R U . . .
C10 C 0.26385(13) 0.5835(4) 0.3727(3) 0.0401(9) Uani 1 1 d . . . . .
C11 C 0.36757(12) 0.6753(3) 0.4519(3) 0.0403(9) Uani 1 1 d . . . . .
C12 C 0.34661(13) 0.7598(4) 0.4996(3) 0.0468(10) Uani 1 1 d . . . . .
H12 H 0.316702 0.752574 0.502580 0.056 Uiso 1 1 calc R U . . .
C13 C 0.36792(14) 0.8549(4) 0.5433(3) 0.0506(10) Uani 1 1 d . . . . .
H13 H 0.352309 0.910189 0.573874 0.061 Uiso 1 1 calc R U . . .
C14 C 0.41191(14) 0.8670(4) 0.5412(3) 0.0451(9) Uani 1 1 d . . . . .
H14 H 0.426638 0.929845 0.571011 0.054 Uiso 1 1 calc R U . . .
C15 C 0.43408(12) 0.7848(3) 0.4943(3) 0.0382(8) Uani 1 1 d . . . . .
C16 C 0.41227(12) 0.6913(3) 0.4486(3) 0.0379(8) Uani 1 1 d . . . . .
C17 C 0.48334(12) 0.6727(4) 0.4282(3) 0.0428(9) Uani 1 1 d . . . . .
C18 C 0.47963(13) 0.7727(4) 0.4821(3) 0.0428(9) Uani 1 1 d . . . . .
C19 C 0.51591(14) 0.8390(4) 0.5100(3) 0.0506(10) Uani 1 1 d . . . . .
H19 H 0.513700 0.906037 0.545963 0.061 Uiso 1 1 calc R U . . .
C20 C 0.55504(15) 0.8040(5) 0.4837(4) 0.0615(13) Uani 1 1 d . . . . .
H20 H 0.579824 0.847417 0.502981 0.074 Uiso 1 1 calc R U . . .
C21 C 0.55914(15) 0.7063(5) 0.4293(4) 0.0634(13) Uani 1 1 d . . . . .
H21 H 0.586397 0.685888 0.411802 0.076 Uiso 1 1 calc R U . . .
C22 C 0.52313(13) 0.6382(4) 0.4003(3) 0.0556(12) Uani 1 1 d . . . . .
H22 H 0.525582 0.572069 0.363665 0.067 Uiso 1 1 calc R U . . .
C23 C 0.43498(12) 0.5343(3) 0.3415(3) 0.0388(8) Uani 1 1 d . . . . .
C24 C 0.39960(17) 0.4776(5) 0.2105(3) 0.0644(14) Uani 1 1 d . . . . .
H24 H 0.379445 0.493809 0.162054 0.077 Uiso 1 1 calc R U . . .
C25 C 0.41971(19) 0.3705(5) 0.2138(4) 0.0696(16) Uani 1 1 d . . . . .
H25 H 0.413834 0.315196 0.167962 0.083 Uiso 1 1 calc R U . . .
C26 C 0.44854(17) 0.3449(5) 0.2847(4) 0.0629(14) Uani 1 1 d . . . . .
H26 H 0.462949 0.272005 0.288186 0.075 Uiso 1 1 calc R U . . .
C27 C 0.45612(14) 0.4279(4) 0.3509(3) 0.0481(10) Uani 1 1 d . . . . .
H27 H 0.475226 0.412190 0.401174 0.058 Uiso 1 1 calc R U . . .
C28 C 0.500000 -0.0262(8) 0.250000 0.099(4) Uani 1 2 d S T P . .
C29 C 0.4638(3) -0.0831(6) 0.2604(5) 0.101(2) Uani 1 1 d . U . . .
H29A H 0.468941 -0.167457 0.258914 0.152 Uiso 1 1 calc R U . . .
H29B H 0.453564 -0.061880 0.317072 0.152 Uiso 1 1 calc R U . . .
H29C H 0.442210 -0.061880 0.212842 0.152 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 C2 1.734(4) . ?
Cl2 C6 1.731(4) . ?
Cl3 C4 1.741(4) . ?
O1 C7 1.209(5) . ?
O2 C10 1.205(5) . ?
O3 C28 1.217(12) . ?
N1 C7 1.394(5) . ?
N1 C10 1.403(5) . ?
N1 C1 1.427(5) . ?
N2 C17 1.400(5) . ?
N2 C16 1.412(5) . ?
N2 C23 1.417(5) . ?
N3 C23 1.322(5) . ?
N3 C24 1.348(6) . ?
C1 C6 1.393(6) . ?
C1 C2 1.395(5) . ?
C2 C3 1.367(6) . ?
C3 C4 1.390(7) . ?
C3 H3 0.9400 . ?
C4 C5 1.381(6) . ?
C5 C6 1.387(6) . ?
C5 H5 0.9400 . ?
C7 C8 1.514(6) . ?
C8 C11 1.521(6) . ?
C8 C9 1.540(6) . ?
C8 H8 0.9900 . ?
C9 C10 1.506(6) . ?
C9 H9A 0.9800 . ?
C9 H9AB 0.9800 . ?
C11 C12 1.396(6) . ?
C11 C16 1.409(5) . ?
C12 C13 1.400(6) . ?
C12 H12 0.9400 . ?
C13 C14 1.380(6) . ?
C13 H13 0.9400 . ?
C14 C15 1.391(6) . ?
C14 H14 0.9400 . ?
C15 C16 1.407(5) . ?
C15 C18 1.453(6) . ?
C17 C22 1.399(6) . ?
C17 C18 1.407(6) . ?
C18 C19 1.391(6) . ?
C19 C20 1.373(7) . ?
C19 H19 0.9400 . ?
C20 C21 1.392(7) . ?
C20 H20 0.9400 . ?
C21 C22 1.400(6) . ?
C21 H21 0.9400 . ?
C22 H22 0.9400 . ?
C23 C27 1.376(6) . ?
C24 C25 1.365(8) . ?
C24 H24 0.9400 . ?
C25 C26 1.367(8) . ?
C25 H25 0.9400 . ?
C26 C27 1.379(7) . ?
C26 H26 0.9400 . ?
C27 H27 0.9400 . ?
C28 C29 1.321(8) . ?
C28 C29 1.321(8) 2_655 ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C29 H29C 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
C7 N1 C10 113.3(3) . . ?
C7 N1 C1 122.9(3) . . ?
C10 N1 C1 123.7(3) . . ?
C17 N2 C16 107.7(3) . . ?
C17 N2 C23 122.5(3) . . ?
C16 N2 C23 128.4(3) . . ?
C23 N3 C24 116.6(4) . . ?
C6 C1 C2 117.8(4) . . ?
C6 C1 N1 120.8(3) . . ?
C2 C1 N1 121.4(3) . . ?
C3 C2 C1 122.2(4) . . ?
C3 C2 Cl1 118.6(3) . . ?
C1 C2 Cl1 119.2(3) . . ?
C2 C3 C4 118.0(4) . . ?
C2 C3 H3 121.0 . . ?
C4 C3 H3 121.0 . . ?
C5 C4 C3 122.5(4) . . ?
C5 C4 Cl3 118.4(4) . . ?
C3 C4 Cl3 119.0(4) . . ?
C4 C5 C6 117.8(4) . . ?
C4 C5 H5 121.1 . . ?
C6 C5 H5 121.1 . . ?
C5 C6 C1 121.7(4) . . ?
C5 C6 Cl2 118.5(3) . . ?
C1 C6 Cl2 119.8(3) . . ?
O1 C7 N1 123.6(4) . . ?
O1 C7 C8 128.0(4) . . ?
N1 C7 C8 108.4(3) . . ?
C7 C8 C11 110.9(3) . . ?
C7 C8 C9 104.4(3) . . ?
C11 C8 C9 114.2(4) . . ?
C7 C8 H8 109.0 . . ?
C11 C8 H8 109.0 . . ?
C9 C8 H8 109.0 . . ?
C10 C9 C8 105.8(3) . . ?
C10 C9 H9A 110.6 . . ?
C8 C9 H9A 110.6 . . ?
C10 C9 H9AB 110.6 . . ?
C8 C9 H9AB 110.6 . . ?
H9A C9 H9AB 108.7 . . ?
O2 C10 N1 123.7(4) . . ?
O2 C10 C9 128.8(4) . . ?
N1 C10 C9 107.5(3) . . ?
C12 C11 C16 116.0(4) . . ?
C12 C11 C8 118.8(3) . . ?
C16 C11 C8 125.2(4) . . ?
C11 C12 C13 123.2(4) . . ?
C11 C12 H12 118.4 . . ?
C13 C12 H12 118.4 . . ?
C14 C13 C12 119.8(4) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C13 C14 C15 118.8(4) . . ?
C13 C14 H14 120.6 . . ?
C15 C14 H14 120.6 . . ?
C14 C15 C16 121.0(4) . . ?
C14 C15 C18 131.4(4) . . ?
C16 C15 C18 107.5(3) . . ?
C15 C16 C11 121.0(3) . . ?
C15 C16 N2 108.6(3) . . ?
C11 C16 N2 130.3(4) . . ?
C22 C17 N2 128.8(4) . . ?
C22 C17 C18 121.3(4) . . ?
N2 C17 C18 109.8(3) . . ?
C19 C18 C17 120.3(4) . . ?
C19 C18 C15 133.4(4) . . ?
C17 C18 C15 106.2(3) . . ?
C20 C19 C18 118.3(4) . . ?
C20 C19 H19 120.9 . . ?
C18 C19 H19 120.9 . . ?
C19 C20 C21 122.1(4) . . ?
C19 C20 H20 119.0 . . ?
C21 C20 H20 119.0 . . ?
C20 C21 C22 120.7(4) . . ?
C20 C21 H21 119.6 . . ?
C22 C21 H21 119.6 . . ?
C17 C22 C21 117.3(4) . . ?
C17 C22 H22 121.4 . . ?
C21 C22 H22 121.4 . . ?
N3 C23 C27 123.9(4) . . ?
N3 C23 N2 116.4(4) . . ?
C27 C23 N2 119.7(4) . . ?
N3 C24 C25 123.3(5) . . ?
N3 C24 H24 118.3 . . ?
C25 C24 H24 118.3 . . ?
C24 C25 C26 119.0(5) . . ?
C24 C25 H25 120.5 . . ?
C26 C25 H25 120.5 . . ?
C25 C26 C27 118.9(5) . . ?
C25 C26 H26 120.6 . . ?
C27 C26 H26 120.6 . . ?
C23 C27 C26 118.2(5) . . ?
C23 C27 H27 120.9 . . ?
C26 C27 H27 120.9 . . ?
O3 C28 C29 119.2(5) . . ?
O3 C28 C29 119.2(5) . 2_655 ?
C29 C28 C29 121.5(10) . 2_655 ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?

_refine_diff_density_max         2.182
_refine_diff_density_min         -0.620
_refine_diff_density_rms         0.111


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetone/ethylactate'
####################################################################### 
# 
# 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_eh_141a_a_sq
_database_code_depnum_ccdc_archive 'CCDC 2177686'
loop_
_audit_author_name
_audit_author_address
'Huiyeong Ju'
;Yeungnam University
South Korea
;
_audit_update_record             
;
2022-06-08 deposited with the CCDC.	2022-08-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
3-(5-Bromo-1-(pyrimidin-2-yl)-1H-indol-2-yl)-1-phenylpyrrolidine-2,5-dione
_chemical_name_common            ?
_chemical_melting_point          514
_chemical_formula_moiety         'C22 H15 Br N4 O2'
_chemical_formula_sum            'C22 H15 Br N4 O2'
_chemical_formula_weight         447.29

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   17.315(11)
_cell_length_b                   7.025(5)
_cell_length_c                   17.444(11)
_cell_angle_alpha                90
_cell_angle_beta                 99.42(3)
_cell_angle_gamma                90
_cell_volume                     2093(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    9228
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      25.53

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_F_000             904
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.246
_exptl_crystal_size_mid          0.185
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    1.988
_shelx_estimated_absorpt_T_min   0.640
_shelx_estimated_absorpt_T_max   0.768
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6719
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            41083
_diffrn_reflns_av_unetI/netI     0.0319
_diffrn_reflns_av_R_equivalents  0.0500
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.367
_diffrn_reflns_theta_max         28.362
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5224
_reflns_number_gt                3651
_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. 
  
 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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0403P)²+1.8044P] 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         5224
_refine_ls_number_parameters     262
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0754
_refine_ls_R_factor_gt           0.0475
_refine_ls_wR_factor_ref         0.1173
_refine_ls_wR_factor_gt          0.1042
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.31497(3) 0.60483(7) 0.79585(2) 0.08627(17) Uani 1 1 d . . . . .
O1 O 0.31413(10) 0.5491(2) 0.29649(9) 0.0388(4) Uani 1 1 d . . . . .
O2 O 0.38643(12) 1.1259(2) 0.21325(12) 0.0518(5) Uani 1 1 d . . . . .
N1 N 0.40721(10) 0.7677(2) 0.48369(11) 0.0292(4) Uani 1 1 d . . . . .
N2 N 0.54319(11) 0.7558(3) 0.50406(12) 0.0438(5) Uani 1 1 d . . . . .
N3 N 0.47070(11) 0.7822(3) 0.37684(12) 0.0368(4) Uani 1 1 d . . . . .
N4 N 0.34577(11) 0.8226(3) 0.23513(11) 0.0307(4) Uani 1 1 d . . . . .
C1 C 0.34823(17) 0.6622(4) 0.69988(15) 0.0477(6) Uani 1 1 d . . . . .
C2 C 0.42788(17) 0.6672(4) 0.69708(15) 0.0459(6) Uani 1 1 d . . . . .
H2 H 0.464016 0.649098 0.742938 0.055 Uiso 1 1 calc R U . . .
C3 C 0.45469(15) 0.6983(3) 0.62792(14) 0.0365(5) Uani 1 1 d . . . . .
H3 H 0.508591 0.699121 0.625793 0.044 Uiso 1 1 calc R U . . .
C4 C 0.39970(13) 0.7284(3) 0.56130(13) 0.0300(5) Uani 1 1 d . . . . .
C5 C 0.31925(14) 0.7263(3) 0.56496(14) 0.0351(5) Uani 1 1 d . . . . .
C6 C 0.29332(16) 0.6908(4) 0.63505(15) 0.0446(6) Uani 1 1 d . . . . .
H6 H 0.239566 0.686559 0.637748 0.053 Uiso 1 1 calc R U . . .
C7 C 0.27865(14) 0.7685(3) 0.48901(14) 0.0354(5) Uani 1 1 d . . . . .
H7 H 0.223988 0.776634 0.474865 0.042 Uiso 1 1 calc R U . . .
C8 C 0.33091(12) 0.7949(3) 0.44080(13) 0.0298(5) Uani 1 1 d . . . . .
C9 C 0.47727(12) 0.7680(3) 0.45337(13) 0.0299(5) Uani 1 1 d . . . . .
C10 C 0.60866(15) 0.7609(4) 0.47291(17) 0.0488(7) Uani 1 1 d . . . . .
H10 H 0.656882 0.750492 0.506369 0.059 Uiso 1 1 calc R U . . .
C11 C 0.60947(15) 0.7802(4) 0.39560(17) 0.0450(6) Uani 1 1 d . . . . .
H11 H 0.656465 0.786687 0.375319 0.054 Uiso 1 1 calc R U . . .
C12 C 0.53769(15) 0.7896(4) 0.34877(16) 0.0437(6) Uani 1 1 d . . . . .
H12 H 0.535741 0.801835 0.294827 0.052 Uiso 1 1 calc R U . . .
C13 C 0.30940(13) 0.8588(3) 0.35827(13) 0.0314(5) Uani 1 1 d . . . . .
H13 H 0.251909 0.876373 0.350002 0.038 Uiso 1 1 calc R U . . .
C14 C 0.32444(12) 0.7191(3) 0.29664(13) 0.0311(5) Uani 1 1 d . . . . .
C15 C 0.36100(13) 1.0130(3) 0.25465(14) 0.0356(5) Uani 1 1 d . . . . .
C16 C 0.34237(14) 1.0475(3) 0.33429(14) 0.0351(5) Uani 1 1 d . . . . .
H16A H 0.303637 1.149529 0.333366 0.042 Uiso 1 1 calc R U . . .
H16B H 0.389646 1.082835 0.370432 0.042 Uiso 1 1 calc R U . . .
C17 C 0.35672(13) 0.7424(3) 0.16261(13) 0.0314(5) Uani 1 1 d . . . . .
C18 C 0.39999(15) 0.5775(4) 0.16067(15) 0.0407(6) Uani 1 1 d . . . . .
H18 H 0.421237 0.515320 0.207068 0.049 Uiso 1 1 calc R U . . .
C19 C 0.41162(17) 0.5051(4) 0.08995(17) 0.0506(7) Uani 1 1 d . . . . .
H19 H 0.441178 0.393471 0.088152 0.061 Uiso 1 1 calc R U . . .
C20 C 0.37995(18) 0.5962(4) 0.02151(16) 0.0521(7) Uani 1 1 d . . . . .
H20 H 0.388919 0.547670 -0.026477 0.063 Uiso 1 1 calc R U . . .
C21 C 0.33550(17) 0.7572(4) 0.02382(15) 0.0483(7) Uani 1 1 d . . . . .
H21 H 0.313327 0.817419 -0.022723 0.058 Uiso 1 1 calc R U . . .
C22 C 0.32320(14) 0.8311(4) 0.09404(14) 0.0386(5) Uani 1 1 d . . . . .
H22 H 0.292358 0.940766 0.095489 0.046 Uiso 1 1 calc R U . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C1 1.901(3) . ?
O1 C14 1.208(3) . ?
O2 C15 1.204(3) . ?
N1 C9 1.400(3) . ?
N1 C4 1.408(3) . ?
N1 C8 1.421(3) . ?
N2 C9 1.327(3) . ?
N2 C10 1.335(3) . ?
N3 C9 1.325(3) . ?
N3 C12 1.332(3) . ?
N4 C14 1.395(3) . ?
N4 C15 1.395(3) . ?
N4 C17 1.425(3) . ?
C1 C6 1.368(4) . ?
C1 C2 1.388(4) . ?
C2 C3 1.379(4) . ?
C2 H2 0.9400 . ?
C3 C4 1.393(3) . ?
C3 H3 0.9400 . ?
C4 C5 1.405(3) . ?
C5 C6 1.392(3) . ?
C5 C7 1.426(3) . ?
C6 H6 0.9400 . ?
C7 C8 1.345(3) . ?
C7 H7 0.9400 . ?
C8 C13 1.496(3) . ?
C10 C11 1.358(4) . ?
C10 H10 0.9400 . ?
C11 C12 1.373(4) . ?
C11 H11 0.9400 . ?
C12 H12 0.9400 . ?
C13 C14 1.509(3) . ?
C13 C16 1.528(3) . ?
C13 H13 0.9900 . ?
C15 C16 1.497(3) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C17 C18 1.383(3) . ?
C17 C22 1.389(3) . ?
C18 C19 1.379(4) . ?
C18 H18 0.9400 . ?
C19 C20 1.386(4) . ?
C19 H19 0.9400 . ?
C20 C21 1.373(4) . ?
C20 H20 0.9400 . ?
C21 C22 1.379(4) . ?
C21 H21 0.9400 . ?
C22 H22 0.9400 . ?

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
C9 N1 C4 125.83(18) . . ?
C9 N1 C8 126.10(19) . . ?
C4 N1 C8 107.96(18) . . ?
C9 N2 C10 115.0(2) . . ?
C9 N3 C12 115.9(2) . . ?
C14 N4 C15 112.05(19) . . ?
C14 N4 C17 124.55(19) . . ?
C15 N4 C17 123.25(19) . . ?
C6 C1 C2 121.8(2) . . ?
C6 C1 Br1 119.3(2) . . ?
C2 C1 Br1 118.8(2) . . ?
C3 C2 C1 120.9(2) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C2 C3 C4 118.2(2) . . ?
C2 C3 H3 120.9 . . ?
C4 C3 H3 120.9 . . ?
C3 C4 C5 120.5(2) . . ?
C3 C4 N1 132.3(2) . . ?
C5 C4 N1 107.09(19) . . ?
C6 C5 C4 120.4(2) . . ?
C6 C5 C7 132.3(2) . . ?
C4 C5 C7 107.3(2) . . ?
C1 C6 C5 118.2(2) . . ?
C1 C6 H6 120.9 . . ?
C5 C6 H6 120.9 . . ?
C8 C7 C5 109.3(2) . . ?
C8 C7 H7 125.4 . . ?
C5 C7 H7 125.4 . . ?
C7 C8 N1 108.4(2) . . ?
C7 C8 C13 123.8(2) . . ?
N1 C8 C13 127.7(2) . . ?
N3 C9 N2 126.8(2) . . ?
N3 C9 N1 116.34(19) . . ?
N2 C9 N1 116.9(2) . . ?
N2 C10 C11 123.7(2) . . ?
N2 C10 H10 118.2 . . ?
C11 C10 H10 118.2 . . ?
C10 C11 C12 116.1(2) . . ?
C10 C11 H11 121.9 . . ?
C12 C11 H11 121.9 . . ?
N3 C12 C11 122.5(3) . . ?
N3 C12 H12 118.7 . . ?
C11 C12 H12 118.7 . . ?
C8 C13 C14 116.46(19) . . ?
C8 C13 C16 118.58(19) . . ?
C14 C13 C16 104.67(19) . . ?
C8 C13 H13 105.3 . . ?
C14 C13 H13 105.3 . . ?
C16 C13 H13 105.3 . . ?
O1 C14 N4 124.9(2) . . ?
O1 C14 C13 127.0(2) . . ?
N4 C14 C13 107.90(19) . . ?
O2 C15 N4 124.0(2) . . ?
O2 C15 C16 127.3(2) . . ?
N4 C15 C16 108.7(2) . . ?
C15 C16 C13 105.11(19) . . ?
C15 C16 H16A 110.7 . . ?
C13 C16 H16A 110.7 . . ?
C15 C16 H16B 110.7 . . ?
C13 C16 H16B 110.7 . . ?
H16A C16 H16B 108.8 . . ?
C18 C17 C22 120.4(2) . . ?
C18 C17 N4 120.3(2) . . ?
C22 C17 N4 119.3(2) . . ?
C19 C18 C17 119.3(2) . . ?
C19 C18 H18 120.3 . . ?
C17 C18 H18 120.3 . . ?
C18 C19 C20 120.4(3) . . ?
C18 C19 H19 119.8 . . ?
C20 C19 H19 119.8 . . ?
C21 C20 C19 120.0(3) . . ?
C21 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C20 C21 C22 120.4(3) . . ?
C20 C21 H21 119.8 . . ?
C22 C21 H21 119.8 . . ?
C21 C22 C17 119.5(2) . . ?
C21 C22 H22 120.2 . . ?
C17 C22 H22 120.2 . . ?

_refine_diff_density_max         0.627
_refine_diff_density_min         -0.755
_refine_diff_density_rms         0.055



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethylacetate'
