# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2143130'
loop_
_audit_author_name
_audit_author_address
'Edward R.T. Tiekink'
;Sunway University
Malaysia
;
_audit_update_record             
;
2022-01-19 deposited with the CCDC.	2022-03-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H17 N5 O'
_chemical_formula_sum            'C19 H17 N5 O'
_chemical_formula_weight         331.38

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'
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'

_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                   11.56480(10)
_cell_length_b                   6.53430(10)
_cell_length_c                   21.5417(2)
_cell_angle_alpha                90
_cell_angle_beta                 97.4430(10)
_cell_angle_gamma                90
_cell_volume                     1614.14(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    13035
_cell_measurement_theta_min      4.1150
_cell_measurement_theta_max      76.3100

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_F_000             696
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.218
_exptl_crystal_size_mid          0.048
_exptl_crystal_size_min          0.027
_exptl_absorpt_coefficient_mu    0.716
_shelx_estimated_absorpt_T_min   0.860
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.757
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'CrysAlisPro [1]'
_diffrn_ambient_temperature      100(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            AtlasS2
_diffrn_detector_area_resol_mean 5.2558
_diffrn_reflns_number            21624
_diffrn_reflns_av_unetI/netI     0.0172
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         4.133
_diffrn_reflns_theta_max         75.298
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3338
_reflns_number_gt                3105
_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       'CrysAlis PRO (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlis PRO (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlis PRO (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXS (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015b)'
_computing_molecular_graphics    
;
ORTEP-3 for Windows (Farrugia, 2012), DIAMOND (Brandenburg, 2006)
;
_computing_publication_material  'PublCIF (Westrip, 2010)'
_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)+(0.0513P)²+0.7365P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3338
_refine_ls_number_parameters     233
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0390
_refine_ls_wR_factor_ref         0.1005
_refine_ls_wR_factor_gt          0.0984
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_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
O4 O 0.34489(7) 0.72000(13) 0.22717(4) 0.0207(2) Uani 1 1 d . . . . .
N1 N 0.44741(8) 0.74017(15) 0.02939(4) 0.0145(2) Uani 1 1 d D . . . .
H1N H 0.4663(12) 0.710(2) -0.0080(5) 0.017 Uiso 1 1 d D U . . .
N2 N 0.38566(8) 0.91876(14) 0.03567(4) 0.0148(2) Uani 1 1 d . . . . .
N5 N 0.44885(8) 0.45103(14) 0.19164(4) 0.0145(2) Uani 1 1 d . . . . .
N7 N 0.50723(8) 0.43701(14) 0.08961(4) 0.0141(2) Uani 1 1 d . . . . .
N31 N 0.29309(8) 1.05875(14) 0.11966(4) 0.0143(2) Uani 1 1 d D . . . .
H31N H 0.2769(12) 1.031(2) 0.1574(5) 0.017 Uiso 1 1 d D U . . .
C3 C 0.35633(9) 0.91155(16) 0.09324(5) 0.0126(2) Uani 1 1 d . . . . .
C3A C 0.39987(9) 0.73023(17) 0.12486(5) 0.0131(2) Uani 1 1 d . . . . .
C4 C 0.39233(9) 0.64480(17) 0.18475(5) 0.0143(2) Uani 1 1 d . . . . .
C6 C 0.50033(9) 0.36157(17) 0.14488(5) 0.0143(2) Uani 1 1 d . . . . .
H6 H 0.534597 0.230880 0.153633 0.017 Uiso 1 1 calc R U . . .
C7A C 0.45521(9) 0.62563(17) 0.08101(5) 0.0129(2) Uani 1 1 d . . . . .
C31 C 0.23787(9) 1.23353(16) 0.09128(5) 0.0130(2) Uani 1 1 d . . . . .
C32 C 0.17322(9) 1.35369(17) 0.12788(5) 0.0149(2) Uani 1 1 d . . . . .
H32 H 0.165971 1.313932 0.169620 0.018 Uiso 1 1 calc R U . . .
C33 C 0.11949(9) 1.53143(17) 0.10325(5) 0.0162(2) Uani 1 1 d . . . . .
H33 H 0.075186 1.611092 0.128539 0.019 Uiso 1 1 calc R U . . .
C34 C 0.12887(10) 1.59585(17) 0.04252(5) 0.0158(2) Uani 1 1 d . . . . .
C35 C 0.19264(10) 1.47248(17) 0.00649(5) 0.0159(2) Uani 1 1 d . . . . .
H35 H 0.199212 1.512043 -0.035348 0.019 Uiso 1 1 calc R U . . .
C36 C 0.24702(9) 1.29309(17) 0.02984(5) 0.0146(2) Uani 1 1 d . . . . .
H36 H 0.289921 1.212025 0.004215 0.018 Uiso 1 1 calc R U . . .
C37 C 0.07269(10) 1.79102(18) 0.01667(6) 0.0201(3) Uani 1 1 d . . . . .
H37A H 0.025010 1.848633 0.046817 0.030 Uiso 1 1 calc R U . . .
H37B H 0.023174 1.762093 -0.022801 0.030 Uiso 1 1 calc R U . . .
H37C H 0.133306 1.889417 0.009154 0.030 Uiso 1 1 calc R U . . .
C51 C 0.45196(10) 0.34004(18) 0.25168(5) 0.0178(2) Uani 1 1 d . . . . .
H51A H 0.438668 0.192458 0.243142 0.021 Uiso 1 1 calc R U . . .
H51B H 0.388193 0.390491 0.274180 0.021 Uiso 1 1 calc R U . . .
C52 C 0.56732(10) 0.36784(19) 0.29280(5) 0.0180(2) Uani 1 1 d . . . . .
C53 C 0.65184(14) 0.2173(2) 0.29531(8) 0.0374(4) Uani 1 1 d . . . . .
H53 H 0.636975 0.095654 0.271463 0.045 Uiso 1 1 calc R U . . .
C54 C 0.75867(15) 0.2429(3) 0.33257(9) 0.0470(4) Uani 1 1 d . . . . .
H54 H 0.816494 0.139283 0.333521 0.056 Uiso 1 1 calc R U . . .
C55 C 0.78111(12) 0.4175(2) 0.36809(6) 0.0297(3) Uani 1 1 d . . . . .
H55 H 0.853495 0.433796 0.394003 0.036 Uiso 1 1 calc R U . . .
C56 C 0.69762(13) 0.5673(3) 0.36551(7) 0.0346(3) Uani 1 1 d . . . . .
H56 H 0.712643 0.688679 0.389475 0.042 Uiso 1 1 calc R U . . .
C57 C 0.59102(12) 0.5431(2) 0.32809(7) 0.0309(3) Uani 1 1 d . . . . .
H57 H 0.533946 0.648099 0.326786 0.037 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
O4 C4 1.2277(14) . ?
N1 C7A 1.3337(14) . ?
N1 N2 1.3838(13) . ?
N1 H1N 0.884(9) . ?
N2 C3 1.3284(14) . ?
N5 C6 1.3660(14) . ?
N5 C4 1.4238(14) . ?
N5 C51 1.4792(14) . ?
N7 C6 1.3006(14) . ?
N7 C7A 1.3734(14) . ?
N31 C3 1.3754(14) . ?
N31 C31 1.4088(14) . ?
N31 H31N 0.877(9) . ?
C3 C3A 1.4256(15) . ?
C3A C7A 1.3877(15) . ?
C3A C4 1.4187(15) . ?
C6 H6 0.9500 . ?
C31 C32 1.3965(15) . ?
C31 C36 1.3966(15) . ?
C32 C33 1.3896(16) . ?
C32 H32 0.9500 . ?
C33 C34 1.3919(16) . ?
C33 H33 0.9500 . ?
C34 C35 1.3945(16) . ?
C34 C37 1.5049(15) . ?
C35 C36 1.3931(15) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
C51 C52 1.5137(16) . ?
C51 H51A 0.9900 . ?
C51 H51B 0.9900 . ?
C52 C57 1.3820(19) . ?
C52 C53 1.3827(18) . ?
C53 C54 1.393(2) . ?
C53 H53 0.9500 . ?
C54 C55 1.380(2) . ?
C54 H54 0.9500 . ?
C55 C56 1.371(2) . ?
C55 H55 0.9500 . ?
C56 C57 1.3919(19) . ?
C56 H56 0.9500 . ?
C57 H57 0.9500 . ?

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
C7A N1 N2 111.82(9) . . ?
C7A N1 H1N 129.7(10) . . ?
N2 N1 H1N 117.8(9) . . ?
C3 N2 N1 105.00(9) . . ?
C6 N5 C4 122.80(9) . . ?
C6 N5 C51 118.12(9) . . ?
C4 N5 C51 119.08(9) . . ?
C6 N7 C7A 112.71(9) . . ?
C3 N31 C31 128.51(9) . . ?
C3 N31 H31N 115.2(10) . . ?
C31 N31 H31N 115.7(10) . . ?
N2 C3 N31 125.12(10) . . ?
N2 C3 C3A 111.00(9) . . ?
N31 C3 C3A 123.88(10) . . ?
C7A C3A C4 120.89(10) . . ?
C7A C3A C3 104.46(9) . . ?
C4 C3A C3 134.58(10) . . ?
O4 C4 C3A 127.25(11) . . ?
O4 C4 N5 121.44(10) . . ?
C3A C4 N5 111.30(9) . . ?
N7 C6 N5 126.66(10) . . ?
N7 C6 H6 116.7 . . ?
N5 C6 H6 116.7 . . ?
N1 C7A N7 126.68(10) . . ?
N1 C7A C3A 107.68(10) . . ?
N7 C7A C3A 125.63(10) . . ?
C32 C31 C36 119.35(10) . . ?
C32 C31 N31 117.16(10) . . ?
C36 C31 N31 123.47(10) . . ?
C33 C32 C31 120.00(10) . . ?
C33 C32 H32 120.0 . . ?
C31 C32 H32 120.0 . . ?
C32 C33 C34 121.75(10) . . ?
C32 C33 H33 119.1 . . ?
C34 C33 H33 119.1 . . ?
C33 C34 C35 117.36(10) . . ?
C33 C34 C37 121.44(10) . . ?
C35 C34 C37 121.20(10) . . ?
C36 C35 C34 122.14(10) . . ?
C36 C35 H35 118.9 . . ?
C34 C35 H35 118.9 . . ?
C35 C36 C31 119.39(10) . . ?
C35 C36 H36 120.3 . . ?
C31 C36 H36 120.3 . . ?
C34 C37 H37A 109.5 . . ?
C34 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
C34 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
N5 C51 C52 111.88(9) . . ?
N5 C51 H51A 109.2 . . ?
C52 C51 H51A 109.2 . . ?
N5 C51 H51B 109.2 . . ?
C52 C51 H51B 109.2 . . ?
H51A C51 H51B 107.9 . . ?
C57 C52 C53 118.63(12) . . ?
C57 C52 C51 121.21(11) . . ?
C53 C52 C51 120.16(12) . . ?
C52 C53 C54 120.44(14) . . ?
C52 C53 H53 119.8 . . ?
C54 C53 H53 119.8 . . ?
C55 C54 C53 120.51(14) . . ?
C55 C54 H54 119.7 . . ?
C53 C54 H54 119.7 . . ?
C56 C55 C54 119.14(13) . . ?
C56 C55 H55 120.4 . . ?
C54 C55 H55 120.4 . . ?
C55 C56 C57 120.58(14) . . ?
C55 C56 H56 119.7 . . ?
C57 C56 H56 119.7 . . ?
C52 C57 C56 120.69(13) . . ?
C52 C57 H57 119.7 . . ?
C56 C57 H57 119.7 . . ?

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
C7A N1 N2 C3 0.51(12) . . . . ?
N1 N2 C3 N31 -179.68(10) . . . . ?
N1 N2 C3 C3A 0.71(12) . . . . ?
C31 N31 C3 N2 6.36(18) . . . . ?
C31 N31 C3 C3A -174.09(10) . . . . ?
N2 C3 C3A C7A -1.60(12) . . . . ?
N31 C3 C3A C7A 178.79(10) . . . . ?
N2 C3 C3A C4 -178.29(11) . . . . ?
N31 C3 C3A C4 2.10(19) . . . . ?
C7A C3A C4 O4 -179.07(11) . . . . ?
C3 C3A C4 O4 -2.8(2) . . . . ?
C7A C3A C4 N5 1.06(14) . . . . ?
C3 C3A C4 N5 177.32(11) . . . . ?
C6 N5 C4 O4 178.65(10) . . . . ?
C51 N5 C4 O4 -1.03(16) . . . . ?
C6 N5 C4 C3A -1.47(14) . . . . ?
C51 N5 C4 C3A 178.84(9) . . . . ?
C7A N7 C6 N5 -0.18(16) . . . . ?
C4 N5 C6 N7 1.14(17) . . . . ?
C51 N5 C6 N7 -179.17(10) . . . . ?
N2 N1 C7A N7 177.82(10) . . . . ?
N2 N1 C7A C3A -1.53(12) . . . . ?
C6 N7 C7A N1 -179.48(10) . . . . ?
C6 N7 C7A C3A -0.24(15) . . . . ?
C4 C3A C7A N1 179.09(9) . . . . ?
C3 C3A C7A N1 1.84(12) . . . . ?
C4 C3A C7A N7 -0.27(17) . . . . ?
C3 C3A C7A N7 -177.52(10) . . . . ?
C3 N31 C31 C32 176.53(10) . . . . ?
C3 N31 C31 C36 -4.95(18) . . . . ?
C36 C31 C32 C33 -0.49(16) . . . . ?
N31 C31 C32 C33 178.09(10) . . . . ?
C31 C32 C33 C34 -0.57(17) . . . . ?
C32 C33 C34 C35 1.30(16) . . . . ?
C32 C33 C34 C37 -178.60(10) . . . . ?
C33 C34 C35 C36 -1.02(17) . . . . ?
C37 C34 C35 C36 178.87(10) . . . . ?
C34 C35 C36 C31 0.01(17) . . . . ?
C32 C31 C36 C35 0.76(16) . . . . ?
N31 C31 C36 C35 -177.73(10) . . . . ?
C6 N5 C51 C52 81.00(12) . . . . ?
C4 N5 C51 C52 -99.30(12) . . . . ?
N5 C51 C52 C57 80.01(14) . . . . ?
N5 C51 C52 C53 -99.52(14) . . . . ?
C57 C52 C53 C54 -0.2(2) . . . . ?
C51 C52 C53 C54 179.34(15) . . . . ?
C52 C53 C54 C55 0.8(3) . . . . ?
C53 C54 C55 C56 -1.0(3) . . . . ?
C54 C55 C56 C57 0.7(2) . . . . ?
C53 C52 C57 C56 -0.2(2) . . . . ?
C51 C52 C57 C56 -179.71(13) . . . . ?
C55 C56 C57 C52 -0.1(2) . . . . ?

_refine_diff_density_max         0.305
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.057

####################################################################### 
# 
# 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_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2143131'
loop_
_audit_author_name
_audit_author_address
'Edward R.T. Tiekink'
;Sunway University
Malaysia
;
_audit_update_record             
;
2022-01-19 deposited with the CCDC.	2022-03-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H14 Br N5 O2'
_chemical_formula_sum            'C18 H14 Br N5 O2'
_chemical_formula_weight         412.25

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'
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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   6.3686(3)
_cell_length_b                   7.5121(3)
_cell_length_c                   17.5514(5)
_cell_angle_alpha                85.174(3)
_cell_angle_beta                 80.226(3)
_cell_angle_gamma                88.510(3)
_cell_volume                     824.51(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    15654
_cell_measurement_theta_min      5.1260
_cell_measurement_theta_max      76.4880

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.661
_exptl_crystal_F_000             416
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.195
_exptl_crystal_size_mid          0.052
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    3.614
_shelx_estimated_absorpt_T_min   0.539
_shelx_estimated_absorpt_T_max   0.899
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.640
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'CrysAlisPro [1]'
_diffrn_ambient_temperature      100(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            AtlasS2
_diffrn_detector_area_resol_mean 5.2558
_diffrn_reflns_number            21039
_diffrn_reflns_av_unetI/netI     0.0239
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         5.131
_diffrn_reflns_theta_max         75.287
_diffrn_reflns_theta_full        67.684
_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             3394
_reflns_number_gt                3299
_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       'CrysAlis PRO (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlis PRO (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlis PRO (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXS (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015b)'
_computing_molecular_graphics    
;
ORTEP-3 for Windows (Farrugia, 2012), DIAMOND (Brandenburg, 2006)
;
_computing_publication_material  'PublCIF (Westrip, 2010)'
_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)+(0.0297P)²+0.6747P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3394
_refine_ls_number_parameters     242
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0263
_refine_ls_R_factor_gt           0.0257
_refine_ls_wR_factor_ref         0.0640
_refine_ls_wR_factor_gt          0.0633
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.002
_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
Br31 Br 0.24694(3) 0.63618(2) 0.91218(2) 0.02439(8) Uani 1 1 d . . . . .
O4 O 0.81302(17) 0.66822(15) 0.40645(6) 0.0158(2) Uani 1 1 d . . . . .
O51 O 0.92864(18) 0.80389(16) 0.04649(6) 0.0183(2) Uani 1 1 d . . . . .
N1 N 1.2727(2) 0.87716(17) 0.55121(8) 0.0130(3) Uani 1 1 d D . . . .
H1N H 1.372(3) 0.933(2) 0.5678(12) 0.016 Uiso 1 1 d D U . . .
N2 N 1.1024(2) 0.80826(17) 0.60409(8) 0.0132(3) Uani 1 1 d . . . . .
N5 N 1.1230(2) 0.80913(17) 0.34461(7) 0.0120(2) Uani 1 1 d . . . . .
N7 N 1.3832(2) 0.91758(17) 0.41219(8) 0.0132(3) Uani 1 1 d . . . . .
N31 N 0.7845(2) 0.65767(17) 0.59051(8) 0.0136(3) Uani 1 1 d D . . . .
H31N H 0.712(3) 0.623(3) 0.5560(10) 0.016 Uiso 1 1 d D U . . .
C3 C 0.9745(2) 0.74167(19) 0.56127(9) 0.0117(3) Uani 1 1 d . . . . .
C3A C 1.0584(2) 0.76874(19) 0.48095(9) 0.0118(3) Uani 1 1 d . . . . .
C4 C 0.9798(2) 0.73958(19) 0.41172(9) 0.0119(3) Uani 1 1 d . . . . .
C6 C 1.3109(2) 0.8896(2) 0.34910(9) 0.0127(3) Uani 1 1 d . . . . .
H6 H 1.397273 0.928925 0.301345 0.015 Uiso 1 1 calc R U . . .
C7A C 1.2487(2) 0.85700(19) 0.47818(9) 0.0118(3) Uani 1 1 d . . . . .
C31 C 0.6712(2) 0.6517(2) 0.66618(9) 0.0129(3) Uani 1 1 d . . . . .
C32 C 0.4673(2) 0.5773(2) 0.67937(9) 0.0143(3) Uani 1 1 d . . . . .
H32 H 0.414393 0.530470 0.637804 0.017 Uiso 1 1 calc R U . . .
C33 C 0.3421(2) 0.5713(2) 0.75214(10) 0.0165(3) Uani 1 1 d . . . . .
H33 H 0.203734 0.521425 0.760562 0.020 Uiso 1 1 calc R U . . .
C34 C 0.4214(3) 0.6391(2) 0.81281(10) 0.0171(3) Uani 1 1 d . . . . .
C35 C 0.6242(3) 0.7099(2) 0.80139(9) 0.0173(3) Uani 1 1 d . . . . .
H35 H 0.676803 0.754646 0.843480 0.021 Uiso 1 1 calc R U . . .
C36 C 0.7509(3) 0.7157(2) 0.72834(9) 0.0154(3) Uani 1 1 d . . . . .
H36 H 0.890682 0.762640 0.720617 0.019 Uiso 1 1 calc R U . . .
C51 C 1.0650(2) 0.8062(2) 0.26844(9) 0.0123(3) Uani 1 1 d . . . . .
C52 C 1.1998(2) 0.7231(2) 0.21117(9) 0.0145(3) Uani 1 1 d . . . . .
H52 H 1.326729 0.665296 0.222437 0.017 Uiso 1 1 calc R U . . .
C53 C 1.1487(2) 0.7248(2) 0.13723(9) 0.0157(3) Uani 1 1 d . . . . .
H53 H 1.240701 0.667896 0.097843 0.019 Uiso 1 1 calc R U . . .
C54 C 0.9623(2) 0.8099(2) 0.12083(9) 0.0140(3) Uani 1 1 d . . . . .
C55 C 0.8279(2) 0.8933(2) 0.17851(9) 0.0156(3) Uani 1 1 d . . . . .
H55 H 0.700618 0.950812 0.167511 0.019 Uiso 1 1 calc R U . . .
C56 C 0.8804(2) 0.8922(2) 0.25252(9) 0.0152(3) Uani 1 1 d . . . . .
H56 H 0.789889 0.950212 0.291890 0.018 Uiso 1 1 calc R U . . .
C57 C 0.7291(3) 0.8685(2) 0.02826(10) 0.0221(3) Uani 1 1 d . . . . .
H57A H 0.613193 0.802419 0.061834 0.033 Uiso 1 1 calc R U . . .
H57B H 0.723366 0.851610 -0.026107 0.033 Uiso 1 1 calc R U . . .
H57C H 0.713456 0.995910 0.036530 0.033 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
Br31 C34 1.9009(17) . ?
O4 C4 1.2226(18) . ?
O51 C54 1.3623(18) . ?
O51 C57 1.426(2) . ?
N1 C7A 1.338(2) . ?
N1 N2 1.3825(18) . ?
N1 H1N 0.873(9) . ?
N2 C3 1.3309(19) . ?
N5 C6 1.3718(19) . ?
N5 C4 1.431(2) . ?
N5 C51 1.4481(18) . ?
N7 C6 1.304(2) . ?
N7 C7A 1.370(2) . ?
N31 C3 1.3785(19) . ?
N31 C31 1.398(2) . ?
N31 H31N 0.878(9) . ?
C3 C3A 1.420(2) . ?
C3A C7A 1.388(2) . ?
C3A C4 1.426(2) . ?
C6 H6 0.9500 . ?
C31 C32 1.402(2) . ?
C31 C36 1.403(2) . ?
C32 C33 1.384(2) . ?
C32 H32 0.9500 . ?
C33 C34 1.391(2) . ?
C33 H33 0.9500 . ?
C34 C35 1.386(2) . ?
C35 C36 1.392(2) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
C51 C56 1.385(2) . ?
C51 C52 1.386(2) . ?
C52 C53 1.390(2) . ?
C52 H52 0.9500 . ?
C53 C54 1.395(2) . ?
C53 H53 0.9500 . ?
C54 C55 1.391(2) . ?
C55 C56 1.395(2) . ?
C55 H55 0.9500 . ?
C56 H56 0.9500 . ?
C57 H57A 0.9800 . ?
C57 H57B 0.9800 . ?
C57 H57C 0.9800 . ?

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
C54 O51 C57 117.86(13) . . ?
C7A N1 N2 111.70(12) . . ?
C7A N1 H1N 128.9(14) . . ?
N2 N1 H1N 119.2(14) . . ?
C3 N2 N1 104.90(12) . . ?
C6 N5 C4 122.73(12) . . ?
C6 N5 C51 117.33(13) . . ?
C4 N5 C51 119.82(12) . . ?
C6 N7 C7A 112.70(12) . . ?
C3 N31 C31 128.10(13) . . ?
C3 N31 H31N 115.9(14) . . ?
C31 N31 H31N 114.6(14) . . ?
N2 C3 N31 124.78(14) . . ?
N2 C3 C3A 111.23(13) . . ?
N31 C3 C3A 123.99(13) . . ?
C7A C3A C3 104.49(13) . . ?
C7A C3A C4 121.08(14) . . ?
C3 C3A C4 134.13(14) . . ?
O4 C4 C3A 127.39(14) . . ?
O4 C4 N5 121.71(13) . . ?
C3A C4 N5 110.90(12) . . ?
N7 C6 N5 126.68(14) . . ?
N7 C6 H6 116.7 . . ?
N5 C6 H6 116.7 . . ?
N1 C7A N7 126.44(13) . . ?
N1 C7A C3A 107.67(13) . . ?
N7 C7A C3A 125.85(14) . . ?
N31 C31 C32 117.26(13) . . ?
N31 C31 C36 123.47(14) . . ?
C32 C31 C36 119.27(14) . . ?
C33 C32 C31 120.87(14) . . ?
C33 C32 H32 119.6 . . ?
C31 C32 H32 119.6 . . ?
C32 C33 C34 119.20(14) . . ?
C32 C33 H33 120.4 . . ?
C34 C33 H33 120.4 . . ?
C35 C34 C33 120.86(15) . . ?
C35 C34 Br31 119.90(12) . . ?
C33 C34 Br31 119.24(12) . . ?
C34 C35 C36 120.11(15) . . ?
C34 C35 H35 119.9 . . ?
C36 C35 H35 119.9 . . ?
C35 C36 C31 119.65(14) . . ?
C35 C36 H36 120.2 . . ?
C31 C36 H36 120.2 . . ?
C56 C51 C52 120.62(14) . . ?
C56 C51 N5 119.91(14) . . ?
C52 C51 N5 119.42(13) . . ?
C51 C52 C53 119.77(14) . . ?
C51 C52 H52 120.1 . . ?
C53 C52 H52 120.1 . . ?
C52 C53 C54 119.99(15) . . ?
C52 C53 H53 120.0 . . ?
C54 C53 H53 120.0 . . ?
O51 C54 C55 125.05(14) . . ?
O51 C54 C53 115.00(14) . . ?
C55 C54 C53 119.95(14) . . ?
C54 C55 C56 119.87(14) . . ?
C54 C55 H55 120.1 . . ?
C56 C55 H55 120.1 . . ?
C51 C56 C55 119.79(15) . . ?
C51 C56 H56 120.1 . . ?
C55 C56 H56 120.1 . . ?
O51 C57 H57A 109.5 . . ?
O51 C57 H57B 109.5 . . ?
H57A C57 H57B 109.5 . . ?
O51 C57 H57C 109.5 . . ?
H57A C57 H57C 109.5 . . ?
H57B C57 H57C 109.5 . . ?

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
C7A N1 N2 C3 1.20(16) . . . . ?
N1 N2 C3 N31 179.42(14) . . . . ?
N1 N2 C3 C3A -0.80(16) . . . . ?
C31 N31 C3 N2 11.9(2) . . . . ?
C31 N31 C3 C3A -167.90(14) . . . . ?
N2 C3 C3A C7A 0.16(17) . . . . ?
N31 C3 C3A C7A 179.94(14) . . . . ?
N2 C3 C3A C4 -173.31(16) . . . . ?
N31 C3 C3A C4 6.5(3) . . . . ?
C7A C3A C4 O4 -178.00(15) . . . . ?
C3 C3A C4 O4 -5.4(3) . . . . ?
C7A C3A C4 N5 1.0(2) . . . . ?
C3 C3A C4 N5 173.64(16) . . . . ?
C6 N5 C4 O4 -179.95(14) . . . . ?
C51 N5 C4 O4 4.0(2) . . . . ?
C6 N5 C4 C3A 0.95(19) . . . . ?
C51 N5 C4 C3A -175.07(13) . . . . ?
C7A N7 C6 N5 -0.1(2) . . . . ?
C4 N5 C6 N7 -1.5(2) . . . . ?
C51 N5 C6 N7 174.59(14) . . . . ?
N2 N1 C7A N7 176.84(13) . . . . ?
N2 N1 C7A C3A -1.13(17) . . . . ?
C6 N7 C7A N1 -175.31(14) . . . . ?
C6 N7 C7A C3A 2.3(2) . . . . ?
C3 C3A C7A N1 0.58(16) . . . . ?
C4 C3A C7A N1 175.11(13) . . . . ?
C3 C3A C7A N7 -177.40(14) . . . . ?
C4 C3A C7A N7 -2.9(2) . . . . ?
C3 N31 C31 C32 171.80(14) . . . . ?
C3 N31 C31 C36 -8.2(2) . . . . ?
N31 C31 C32 C33 -178.04(14) . . . . ?
C36 C31 C32 C33 1.9(2) . . . . ?
C31 C32 C33 C34 -0.4(2) . . . . ?
C32 C33 C34 C35 -0.9(2) . . . . ?
C32 C33 C34 Br31 178.47(11) . . . . ?
C33 C34 C35 C36 0.6(2) . . . . ?
Br31 C34 C35 C36 -178.70(12) . . . . ?
C34 C35 C36 C31 0.9(2) . . . . ?
N31 C31 C36 C35 177.83(14) . . . . ?
C32 C31 C36 C35 -2.2(2) . . . . ?
C6 N5 C51 C56 -117.89(16) . . . . ?
C4 N5 C51 C56 58.34(19) . . . . ?
C6 N5 C51 C52 59.52(19) . . . . ?
C4 N5 C51 C52 -124.24(15) . . . . ?
C56 C51 C52 C53 -0.5(2) . . . . ?
N5 C51 C52 C53 -177.92(13) . . . . ?
C51 C52 C53 C54 0.0(2) . . . . ?
C57 O51 C54 C55 -8.0(2) . . . . ?
C57 O51 C54 C53 172.35(14) . . . . ?
C52 C53 C54 O51 179.73(14) . . . . ?
C52 C53 C54 C55 0.1(2) . . . . ?
O51 C54 C55 C56 -179.34(14) . . . . ?
C53 C54 C55 C56 0.3(2) . . . . ?
C52 C51 C56 C55 0.9(2) . . . . ?
N5 C51 C56 C55 178.27(13) . . . . ?
C54 C55 C56 C51 -0.8(2) . . . . ?

_refine_diff_density_max         0.515
_refine_diff_density_min         -0.808
_refine_diff_density_rms         0.070

