# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2298509'
loop_
_audit_author_name
_audit_author_address
'Dr. Shobhana Krishnaswamy'
;IIT Madras
India
;
_audit_update_record             
;
2023-09-30 deposited with the CCDC.	2024-02-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H24 Br2 N4 O'
_chemical_formula_weight         580.32

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
'x-1/2, y, -z-1/2'

_cell_length_a                   10.1637(6)
_cell_length_b                   19.7936(11)
_cell_length_c                   25.9343(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5217.4(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    9949
_cell_measurement_theta_min      2.75
_cell_measurement_theta_max      23.36

_exptl_crystal_description       block
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.478
_exptl_crystal_F_000             2336
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.279
_exptl_crystal_size_mid          0.091
_exptl_crystal_size_min          0.042
_exptl_absorpt_coefficient_mu    3.134
_shelx_estimated_absorpt_T_min   0.475
_shelx_estimated_absorpt_T_max   0.880
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5861
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'SADABS-2016/2 - Bruker AXS'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine focus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 Venture Diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            167455
_diffrn_reflns_av_unetI/netI     0.0362
_diffrn_reflns_av_R_equivalents  0.1872
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         3.260
_diffrn_reflns_theta_max         25.057
_diffrn_reflns_theta_full        25.057
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4609
_reflns_number_gt                3154
_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       'APEX4(Bruker, 2021)'
_computing_cell_refinement       'APEX4/SAINT (Bruker, 2021)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2021)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019), WinGX'
_computing_molecular_graphics    'ORTEP3 (Farrugia, 2012)'
_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)+(0.0759P)²+2.9330P] 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         4609
_refine_ls_number_parameters     310
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0903
_refine_ls_R_factor_gt           0.0531
_refine_ls_wR_factor_ref         0.1443
_refine_ls_wR_factor_gt          0.1253
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_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
C1 C 0.9740(5) 0.5564(2) 0.6046(2) 0.0498(12) Uani 1 1 d . . . . .
C2 C 1.0912(5) 0.5348(3) 0.5822(2) 0.0559(13) Uani 1 1 d . . . . .
H2 H 1.163386 0.563609 0.580700 0.067 Uiso 1 1 calc R U . . .
C3 C 1.0996(5) 0.4705(3) 0.5625(2) 0.0549(13) Uani 1 1 d . . . . .
H3 H 1.176823 0.454933 0.547358 0.066 Uiso 1 1 calc R U . . .
C4 C 0.9890(4) 0.4294(2) 0.56584(18) 0.0437(11) Uani 1 1 d . . . . .
C5 C 0.8441(5) 0.3460(2) 0.56041(19) 0.0482(12) Uani 1 1 d . . . . .
H5 H 0.807932 0.304053 0.552505 0.058 Uiso 1 1 calc R U . . .
C6 C 0.7777(4) 0.39726(19) 0.58407(17) 0.0374(10) Uani 1 1 d . . . . .
C7 C 0.8702(4) 0.4516(2) 0.58801(17) 0.0380(10) Uani 1 1 d . . . . .
C8 C 0.8633(4) 0.5172(2) 0.60818(19) 0.0438(11) Uani 1 1 d . . . . .
H8 H 0.786710 0.533394 0.623387 0.053 Uiso 1 1 calc R U . . .
C9 C 1.0687(6) 0.3219(3) 0.5242(3) 0.0825(19) Uani 1 1 d . . . . .
H9A H 1.105273 0.345892 0.495376 0.124 Uiso 1 1 calc R U . . .
H9B H 1.027415 0.281194 0.512247 0.124 Uiso 1 1 calc R U . . .
H9C H 1.137528 0.310764 0.548057 0.124 Uiso 1 1 calc R U . . .
C10 C 0.7742(5) 0.3447(3) 0.7626(2) 0.0567(13) Uani 1 1 d . . . . .
C11 C 0.7101(6) 0.3802(3) 0.8019(2) 0.0667(15) Uani 1 1 d . . . . .
H11 H 0.728410 0.370461 0.836244 0.080 Uiso 1 1 calc R U . . .
C12 C 0.6203(6) 0.4291(3) 0.7897(2) 0.0668(15) Uani 1 1 d . . . . .
H12 H 0.577482 0.453286 0.815481 0.080 Uiso 1 1 calc R U . . .
C13 C 0.5944(5) 0.4419(2) 0.7380(2) 0.0538(13) Uani 1 1 d . . . . .
C14 C 0.5155(5) 0.4775(2) 0.6632(2) 0.0533(13) Uani 1 1 d . . . . .
H14 H 0.464950 0.501496 0.639588 0.064 Uiso 1 1 calc R U . . .
C15 C 0.6063(4) 0.4292(2) 0.65009(18) 0.0412(10) Uani 1 1 d . . . . .
C16 C 0.6592(4) 0.4057(2) 0.69814(18) 0.0415(11) Uani 1 1 d . . . . .
C17 C 0.7520(5) 0.3570(2) 0.71124(18) 0.0461(11) Uani 1 1 d . . . . .
H17 H 0.797637 0.333416 0.685921 0.055 Uiso 1 1 calc R U . . .
C18 C 0.4218(6) 0.5322(3) 0.7427(3) 0.085(2) Uani 1 1 d . . . . .
H18A H 0.472750 0.568056 0.757618 0.127 Uiso 1 1 calc R U . . .
H18B H 0.376638 0.508108 0.769526 0.127 Uiso 1 1 calc R U . . .
H18C H 0.358710 0.550811 0.719104 0.127 Uiso 1 1 calc R U . . .
C19 C 0.6315(4) 0.3993(2) 0.59723(17) 0.0377(10) Uani 1 1 d . . . . .
C20 C 0.5720(5) 0.3272(2) 0.5959(2) 0.0506(12) Uani 1 1 d . . . . .
H20A H 0.611139 0.300277 0.622529 0.076 Uiso 1 1 calc R U . . .
H20B H 0.589328 0.306979 0.562908 0.076 Uiso 1 1 calc R U . . .
H20C H 0.478693 0.329790 0.601261 0.076 Uiso 1 1 calc R U . . .
C21 C 0.5619(4) 0.4438(2) 0.55692(19) 0.0479(12) Uani 1 1 d . . . . .
H21A H 0.469795 0.448247 0.566083 0.057 Uiso 1 1 calc R U . . .
H21B H 0.600808 0.488499 0.557212 0.057 Uiso 1 1 calc R U . . .
C22 C 0.4695(5) 0.3899(2) 0.4799(2) 0.0471(12) Uani 1 1 d . . . . .
C23 C 0.4990(4) 0.3593(2) 0.4289(2) 0.0478(12) Uani 1 1 d . . . . .
C24 C 0.3983(5) 0.3373(2) 0.3977(2) 0.0559(13) Uani 1 1 d . . . . .
H24 H 0.311304 0.342045 0.408216 0.067 Uiso 1 1 calc R U . . .
C25 C 0.4267(6) 0.3087(3) 0.3514(2) 0.0728(16) Uani 1 1 d . . . . .
H25 H 0.359752 0.294306 0.329531 0.087 Uiso 1 1 calc R U . . .
C26 C 0.5562(7) 0.3015(4) 0.3375(3) 0.089(2) Uani 1 1 d . . . . .
H26 H 0.579013 0.281167 0.306463 0.107 Uiso 1 1 calc R U . . .
C27 C 0.6522(6) 0.3251(4) 0.3708(3) 0.094(2) Uani 1 1 d . . . . .
H27 H 0.739921 0.320405 0.361220 0.113 Uiso 1 1 calc R U . . .
N1 N 0.9709(4) 0.36447(18) 0.54991(16) 0.0506(10) Uani 1 1 d . . . . .
N2 N 0.5089(4) 0.4860(2) 0.71514(17) 0.0601(12) Uani 1 1 d . . . . .
N3 N 0.5721(4) 0.41552(19) 0.50536(15) 0.0481(10) Uani 1 1 d . . . . .
H3A H 0.647768 0.415323 0.490540 0.058 Uiso 1 1 calc R U . . .
N4 N 0.6252(4) 0.3542(3) 0.4158(2) 0.0710(14) Uani 1 1 d . . . . .
Br1 Br 0.96887(6) 0.64637(3) 0.63176(3) 0.0755(2) Uani 1 1 d . . . . .
Br2 Br 0.89446(6) 0.27549(3) 0.78181(2) 0.0751(2) Uani 1 1 d . . . . .
O1 O 0.3561(3) 0.3920(2) 0.49632(16) 0.0755(12) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C8 1.371(6) . ?
C1 C2 1.392(7) . ?
C1 Br1 1.915(5) . ?
C2 C3 1.375(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.390(6) . ?
C3 H3 0.9300 . ?
C4 N1 1.363(6) . ?
C4 C7 1.408(6) . ?
C5 C6 1.365(6) . ?
C5 N1 1.367(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.432(6) . ?
C6 C19 1.525(6) . ?
C7 C8 1.402(6) . ?
C8 H8 0.9300 . ?
C9 N1 1.464(6) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C17 1.372(7) . ?
C10 C11 1.399(8) . ?
C10 Br2 1.903(5) . ?
C11 C12 1.368(8) . ?
C11 H11 0.9300 . ?
C12 C13 1.391(7) . ?
C12 H12 0.9300 . ?
C13 N2 1.365(7) . ?
C13 C16 1.420(7) . ?
C14 N2 1.358(7) . ?
C14 C15 1.372(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.434(6) . ?
C15 C19 1.515(6) . ?
C16 C17 1.391(6) . ?
C17 H17 0.9300 . ?
C18 N2 1.460(7) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C21 1.538(6) . ?
C19 C20 1.550(6) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 N3 1.453(6) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 O1 1.229(6) . ?
C22 N3 1.334(6) . ?
C22 C23 1.486(7) . ?
C23 N4 1.330(6) . ?
C23 C24 1.376(7) . ?
C24 C25 1.359(8) . ?
C24 H24 0.9300 . ?
C25 C26 1.372(9) . ?
C25 H25 0.9300 . ?
C26 C27 1.384(9) . ?
C26 H26 0.9300 . ?
C27 N4 1.331(7) . ?
C27 H27 0.9300 . ?
N3 H3A 0.8600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 C1 C2 123.8(4) . . ?
C8 C1 Br1 118.7(4) . . ?
C2 C1 Br1 117.6(3) . . ?
C3 C2 C1 119.5(4) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C2 C3 C4 117.9(5) . . ?
C2 C3 H3 121.0 . . ?
C4 C3 H3 121.0 . . ?
N1 C4 C3 130.0(4) . . ?
N1 C4 C7 107.6(4) . . ?
C3 C4 C7 122.5(4) . . ?
C6 C5 N1 110.9(4) . . ?
C6 C5 H5 124.6 . . ?
N1 C5 H5 124.6 . . ?
C5 C6 C7 105.4(4) . . ?
C5 C6 C19 127.0(4) . . ?
C7 C6 C19 127.2(4) . . ?
C8 C7 C4 119.0(4) . . ?
C8 C7 C6 133.6(4) . . ?
C4 C7 C6 107.5(4) . . ?
C1 C8 C7 117.3(4) . . ?
C1 C8 H8 121.3 . . ?
C7 C8 H8 121.3 . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C17 C10 C11 122.8(5) . . ?
C17 C10 Br2 119.2(4) . . ?
C11 C10 Br2 118.0(4) . . ?
C12 C11 C10 119.8(5) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C11 C12 C13 118.6(5) . . ?
C11 C12 H12 120.7 . . ?
C13 C12 H12 120.7 . . ?
N2 C13 C12 130.9(5) . . ?
N2 C13 C16 107.6(5) . . ?
C12 C13 C16 121.5(5) . . ?
N2 C14 C15 111.4(5) . . ?
N2 C14 H14 124.3 . . ?
C15 C14 H14 124.3 . . ?
C14 C15 C16 105.2(4) . . ?
C14 C15 C19 127.6(4) . . ?
C16 C15 C19 126.6(4) . . ?
C17 C16 C13 119.1(4) . . ?
C17 C16 C15 133.7(4) . . ?
C13 C16 C15 107.1(4) . . ?
C10 C17 C16 118.1(4) . . ?
C10 C17 H17 120.9 . . ?
C16 C17 H17 120.9 . . ?
N2 C18 H18A 109.5 . . ?
N2 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N2 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C15 C19 C6 112.2(3) . . ?
C15 C19 C21 108.3(4) . . ?
C6 C19 C21 108.1(4) . . ?
C15 C19 C20 108.3(3) . . ?
C6 C19 C20 110.5(3) . . ?
C21 C19 C20 109.4(4) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N3 C21 C19 111.9(4) . . ?
N3 C21 H21A 109.2 . . ?
C19 C21 H21A 109.2 . . ?
N3 C21 H21B 109.2 . . ?
C19 C21 H21B 109.2 . . ?
H21A C21 H21B 107.9 . . ?
O1 C22 N3 123.3(5) . . ?
O1 C22 C23 120.8(4) . . ?
N3 C22 C23 115.9(4) . . ?
N4 C23 C24 122.9(5) . . ?
N4 C23 C22 116.9(4) . . ?
C24 C23 C22 120.2(4) . . ?
C25 C24 C23 119.6(5) . . ?
C25 C24 H24 120.2 . . ?
C23 C24 H24 120.2 . . ?
C24 C25 C26 118.6(6) . . ?
C24 C25 H25 120.7 . . ?
C26 C25 H25 120.7 . . ?
C25 C26 C27 118.6(6) . . ?
C25 C26 H26 120.7 . . ?
C27 C26 H26 120.7 . . ?
N4 C27 C26 123.2(6) . . ?
N4 C27 H27 118.4 . . ?
C26 C27 H27 118.4 . . ?
C4 N1 C5 108.7(4) . . ?
C4 N1 C9 126.1(4) . . ?
C5 N1 C9 125.2(4) . . ?
C14 N2 C13 108.7(4) . . ?
C14 N2 C18 126.3(5) . . ?
C13 N2 C18 125.0(5) . . ?
C22 N3 C21 123.1(4) . . ?
C22 N3 H3A 118.5 . . ?
C21 N3 H3A 118.5 . . ?
C27 N4 C23 117.1(5) . . ?

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
C8 C1 C2 C3 -0.3(8) . . . . ?
Br1 C1 C2 C3 179.7(4) . . . . ?
C1 C2 C3 C4 -0.1(8) . . . . ?
C2 C3 C4 N1 -179.6(5) . . . . ?
C2 C3 C4 C7 0.7(8) . . . . ?
N1 C5 C6 C7 0.5(5) . . . . ?
N1 C5 C6 C19 173.5(4) . . . . ?
N1 C4 C7 C8 179.2(4) . . . . ?
C3 C4 C7 C8 -0.9(7) . . . . ?
N1 C4 C7 C6 -0.9(5) . . . . ?
C3 C4 C7 C6 178.9(4) . . . . ?
C5 C6 C7 C8 -180.0(5) . . . . ?
C19 C6 C7 C8 7.0(8) . . . . ?
C5 C6 C7 C4 0.3(5) . . . . ?
C19 C6 C7 C4 -172.8(4) . . . . ?
C2 C1 C8 C7 0.0(7) . . . . ?
Br1 C1 C8 C7 -179.9(3) . . . . ?
C4 C7 C8 C1 0.6(6) . . . . ?
C6 C7 C8 C1 -179.2(5) . . . . ?
C17 C10 C11 C12 0.4(9) . . . . ?
Br2 C10 C11 C12 -178.3(4) . . . . ?
C10 C11 C12 C13 0.5(8) . . . . ?
C11 C12 C13 N2 178.3(5) . . . . ?
C11 C12 C13 C16 -0.3(8) . . . . ?
N2 C14 C15 C16 0.3(5) . . . . ?
N2 C14 C15 C19 172.2(4) . . . . ?
N2 C13 C16 C17 -179.8(4) . . . . ?
C12 C13 C16 C17 -0.9(7) . . . . ?
N2 C13 C16 C15 -1.2(5) . . . . ?
C12 C13 C16 C15 177.6(5) . . . . ?
C14 C15 C16 C17 178.8(5) . . . . ?
C19 C15 C16 C17 6.8(8) . . . . ?
C14 C15 C16 C13 0.6(5) . . . . ?
C19 C15 C16 C13 -171.4(4) . . . . ?
C11 C10 C17 C16 -1.6(7) . . . . ?
Br2 C10 C17 C16 177.1(3) . . . . ?
C13 C16 C17 C10 1.8(6) . . . . ?
C15 C16 C17 C10 -176.3(5) . . . . ?
C14 C15 C19 C6 132.8(5) . . . . ?
C16 C15 C19 C6 -57.0(5) . . . . ?
C14 C15 C19 C21 13.6(6) . . . . ?
C16 C15 C19 C21 -176.2(4) . . . . ?
C14 C15 C19 C20 -105.0(5) . . . . ?
C16 C15 C19 C20 65.3(5) . . . . ?
C5 C6 C19 C15 138.5(5) . . . . ?
C7 C6 C19 C15 -50.0(6) . . . . ?
C5 C6 C19 C21 -102.2(5) . . . . ?
C7 C6 C19 C21 69.4(5) . . . . ?
C5 C6 C19 C20 17.5(6) . . . . ?
C7 C6 C19 C20 -171.0(4) . . . . ?
C15 C19 C21 N3 -175.3(3) . . . . ?
C6 C19 C21 N3 62.9(5) . . . . ?
C20 C19 C21 N3 -57.4(5) . . . . ?
O1 C22 C23 N4 -174.9(5) . . . . ?
N3 C22 C23 N4 6.6(6) . . . . ?
O1 C22 C23 C24 4.7(7) . . . . ?
N3 C22 C23 C24 -173.9(4) . . . . ?
N4 C23 C24 C25 0.3(8) . . . . ?
C22 C23 C24 C25 -179.2(5) . . . . ?
C23 C24 C25 C26 1.2(9) . . . . ?
C24 C25 C26 C27 -1.5(11) . . . . ?
C25 C26 C27 N4 0.4(12) . . . . ?
C3 C4 N1 C5 -178.5(5) . . . . ?
C7 C4 N1 C5 1.3(5) . . . . ?
C3 C4 N1 C9 -0.5(9) . . . . ?
C7 C4 N1 C9 179.3(5) . . . . ?
C6 C5 N1 C4 -1.1(6) . . . . ?
C6 C5 N1 C9 -179.2(5) . . . . ?
C15 C14 N2 C13 -1.2(6) . . . . ?
C15 C14 N2 C18 -178.9(5) . . . . ?
C12 C13 N2 C14 -177.3(5) . . . . ?
C16 C13 N2 C14 1.5(5) . . . . ?
C12 C13 N2 C18 0.5(9) . . . . ?
C16 C13 N2 C18 179.2(5) . . . . ?
O1 C22 N3 C21 5.1(7) . . . . ?
C23 C22 N3 C21 -176.4(4) . . . . ?
C19 C21 N3 C22 110.6(5) . . . . ?
C26 C27 N4 C23 1.1(11) . . . . ?
C24 C23 N4 C27 -1.4(9) . . . . ?
C22 C23 N4 C27 178.1(6) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C2 H2 N4 0.93 2.70 3.624(6) 175.5 5_766 yes
C3 H3 O1 0.93 2.57 3.486(6) 167.1 1_655 yes
C24 H24 Br1 0.93 3.04 3.823(5) 143.0 5_666 yes
C27 H27 Br1 0.93 3.04 3.893(6) 153.7 5_766 yes

_refine_diff_density_max         0.356
_refine_diff_density_min         -0.646
_refine_diff_density_rms         0.062


# start Validation Reply Form
_vrf_RINTA01_shelx               
;
PROBLEM: The value of Rint is greater than 0.18
RESPONSE: The crystal exhibited weak diffraction, especially at 
higher angles. No resolution cut-offs were applied during the
refinement and the weak data have been retained.    
;
# end Validation Reply Form
