# Supplementary Information (SI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2026

####################################################################### 
# 
# 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_1552_ares
_database_code_depnum_ccdc_archive 'CCDC 2424232'
loop_
_audit_author_name
_audit_author_address
'ADITI DHAR'
;CALCUTTA UNIVERSITY
India
;
_audit_update_record             
;
2025-02-16 deposited with the CCDC.	2025-12-22 downloaded from the CCDC.
;
_audit_creation_date             2024-03-19
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H12 Br Cu N5 O'
_chemical_formula_sum            'C16 H12 Br Cu N5 O'
_chemical_formula_weight         433.76
_chemical_melting_point          ?
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'
Cu Cu 0.3201 1.2651 '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'

_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                   7.2840(2)
_cell_length_b                   18.1468(5)
_cell_length_c                   12.2852(3)
_cell_angle_alpha                90
_cell_angle_beta                 102.552(2)
_cell_angle_gamma                90
_cell_volume                     1585.06(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5433
_cell_measurement_temperature    296.00
_cell_measurement_theta_max      23.24
_cell_measurement_theta_min      2.69
_shelx_estimated_absorpt_T_max   0.407
_shelx_estimated_absorpt_T_min   0.341
_exptl_absorpt_coefficient_mu    3.912
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear dark brown'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.818
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             860
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.28
_exptl_transmission_factor_max   0.334
_exptl_transmission_factor_min   0.264
_diffrn_reflns_av_R_equivalents  0.0668
_diffrn_reflns_av_unetI/netI     0.0452
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            21287
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         3.077
_diffrn_ambient_temperature      296.00
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'Bruker SMART CCD 1K area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART CCD 1K'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_target            Mo
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2048
_reflns_number_total             2794
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.555
_refine_diff_density_min         -0.523
_refine_diff_density_rms         0.113
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2794
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0646
_refine_ls_R_factor_gt           0.0369
_refine_ls_restrained_S_all      1.034
_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)+(0.0346P)²+0.2938P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0683
_refine_ls_wR_factor_ref         0.0743
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C6(H6A,H6B)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C10(H10), C12(H12), C13(H13), C1(H1), C3(H3), C2(H2), C4(H4)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
Cu1 Cu 0.19230(6) 0.51816(2) 0.59279(3) 0.02928(14) Uani 1 1 d . . . . .
Br1 Br 0.24948(7) 0.11586(2) 0.57709(4) 0.05194(16) Uani 1 1 d . . . . .
O1 O 0.1374(3) 0.43989(12) 0.48260(17) 0.0329(6) Uani 1 1 d . . . . .
N2 N 0.0988(4) 0.45495(16) 0.6997(2) 0.0269(7) Uani 1 1 d . . . . .
N1 N 0.2335(4) 0.60846(15) 0.6962(2) 0.0315(7) Uani 1 1 d . . . . .
N3 N 0.3201(4) 0.56744(16) 0.4832(3) 0.0358(8) Uani 1 1 d . . . . .
N4 N 0.4782(4) 0.5432(2) 0.3300(3) 0.0468(9) Uani 1 1 d . . . . .
C15 C 0.3867(5) 0.55703(19) 0.4088(3) 0.0318(9) Uani 1 1 d . . . . .
C14 C 0.1704(5) 0.37067(19) 0.5082(3) 0.0286(8) Uani 1 1 d . . . . .
C8 C 0.0924(5) 0.3848(2) 0.6949(3) 0.0316(9) Uani 1 1 d . . . . .
H8 H 0.051129 0.360545 0.751844 0.038 Uiso 1 1 calc R U . . .
C5 C 0.2366(5) 0.60758(19) 0.8065(3) 0.0325(9) Uani 1 1 d . . . . .
C10 C 0.1647(5) 0.2637(2) 0.6275(3) 0.0347(9) Uani 1 1 d . . . . .
H10 H 0.140594 0.243314 0.692439 0.042 Uiso 1 1 calc R U . . .
C9 C 0.1434(5) 0.33927(19) 0.6093(3) 0.0281(8) Uani 1 1 d . . . . .
C16 C 0.4185(5) 0.5670(2) 0.2286(3) 0.0374(10) Uani 1 1 d . . . . .
C7 C 0.0437(5) 0.4913(2) 0.7939(3) 0.0356(9) Uani 1 1 d . . . . .
H7A H 0.006254 0.454365 0.841993 0.043 Uiso 1 1 calc R U . . .
H7B H -0.063424 0.523061 0.766635 0.043 Uiso 1 1 calc R U . . .
C12 C 0.2589(5) 0.2490(2) 0.4541(3) 0.0380(9) Uani 1 1 d . . . . .
H12 H 0.302157 0.219104 0.403567 0.046 Uiso 1 1 calc R U . . .
C6 C 0.2038(5) 0.5364(2) 0.8602(3) 0.0367(9) Uani 1 1 d . . . . .
H6A H 0.178239 0.546685 0.932901 0.044 Uiso 1 1 calc R U . . .
H6B H 0.318079 0.507250 0.871550 0.044 Uiso 1 1 calc R U . . .
C11 C 0.2208(5) 0.21890(19) 0.5510(3) 0.0348(9) Uani 1 1 d . . . . .
C13 C 0.2323(5) 0.3228(2) 0.4335(3) 0.0383(10) Uani 1 1 d . . . . .
H13 H 0.256116 0.341991 0.367735 0.046 Uiso 1 1 calc R U . . .
N5 N 0.3797(6) 0.5847(2) 0.1379(3) 0.0728(13) Uani 1 1 d . . . . .
C1 C 0.2596(6) 0.6739(2) 0.6500(3) 0.0459(11) Uani 1 1 d . . . . .
H1 H 0.253950 0.675489 0.573681 0.055 Uiso 1 1 calc R U . . .
C3 C 0.2997(6) 0.7368(2) 0.8210(4) 0.0502(11) Uani 1 1 d . . . . .
H3 H 0.323440 0.779685 0.863290 0.060 Uiso 1 1 calc R U . . .
C2 C 0.2939(6) 0.7381(2) 0.7091(4) 0.0532(12) Uani 1 1 d . . . . .
H2 H 0.312891 0.781848 0.673802 0.064 Uiso 1 1 calc R U . . .
C4 C 0.2700(6) 0.6715(2) 0.8697(3) 0.0434(10) Uani 1 1 d . . . . .
H4 H 0.272094 0.669882 0.945610 0.052 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
Cu1 O1 1.943(2) . ?
Cu1 N2 1.973(3) . ?
Cu1 N1 2.055(3) . ?
Cu1 N3 2.006(3) . ?
Br1 C11 1.901(4) . ?
O1 C14 1.304(4) . ?
N2 C8 1.275(4) . ?
N2 C7 1.462(4) . ?
N1 C5 1.350(4) . ?
N1 C1 1.348(4) . ?
N3 C15 1.140(4) . ?
N4 C15 1.313(5) . ?
N4 C16 1.301(5) . ?
C14 C9 1.419(5) . ?
C14 C13 1.407(5) . ?
C8 H8 0.9300 . ?
C8 C9 1.448(5) . ?
C5 C6 1.493(5) . ?
C5 C4 1.388(5) . ?
C10 H10 0.9300 . ?
C10 C9 1.393(5) . ?
C10 C11 1.369(5) . ?
C16 N5 1.135(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C6 1.510(5) . ?
C12 H12 0.9300 . ?
C12 C11 1.391(5) . ?
C12 C13 1.369(5) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C13 H13 0.9300 . ?
C1 H1 0.9300 . ?
C1 C2 1.366(5) . ?
C3 H3 0.9300 . ?
C3 C2 1.366(5) . ?
C3 C4 1.366(5) . ?
C2 H2 0.9300 . ?
C4 H4 0.9300 . ?

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
O1 Cu1 N2 89.44(11) . . ?
O1 Cu1 N1 173.70(11) . . ?
O1 Cu1 N3 85.04(11) . . ?
N2 Cu1 N1 94.42(11) . . ?
N2 Cu1 N3 169.60(12) . . ?
N3 Cu1 N1 91.87(12) . . ?
C14 O1 Cu1 122.5(2) . . ?
C8 N2 Cu1 124.3(2) . . ?
C8 N2 C7 118.2(3) . . ?
C7 N2 Cu1 117.3(2) . . ?
C5 N1 Cu1 125.4(2) . . ?
C1 N1 Cu1 117.2(2) . . ?
C1 N1 C5 117.4(3) . . ?
C15 N3 Cu1 143.6(3) . . ?
C16 N4 C15 121.6(3) . . ?
N3 C15 N4 174.5(4) . . ?
O1 C14 C9 123.0(3) . . ?
O1 C14 C13 120.4(3) . . ?
C13 C14 C9 116.6(3) . . ?
N2 C8 H8 116.9 . . ?
N2 C8 C9 126.2(3) . . ?
C9 C8 H8 116.9 . . ?
N1 C5 C6 118.9(3) . . ?
N1 C5 C4 120.9(3) . . ?
C4 C5 C6 120.1(3) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 H10 119.5 . . ?
C11 C10 C9 120.9(3) . . ?
C14 C9 C8 120.9(3) . . ?
C10 C9 C14 120.3(3) . . ?
C10 C9 C8 118.9(3) . . ?
N5 C16 N4 173.9(4) . . ?
N2 C7 H7A 109.4 . . ?
N2 C7 H7B 109.4 . . ?
N2 C7 C6 111.0(3) . . ?
H7A C7 H7B 108.0 . . ?
C6 C7 H7A 109.4 . . ?
C6 C7 H7B 109.4 . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
C13 C12 C11 119.7(3) . . ?
C5 C6 C7 114.2(3) . . ?
C5 C6 H6A 108.7 . . ?
C5 C6 H6B 108.7 . . ?
C7 C6 H6A 108.7 . . ?
C7 C6 H6B 108.7 . . ?
H6A C6 H6B 107.6 . . ?
C10 C11 Br1 120.4(3) . . ?
C10 C11 C12 119.9(3) . . ?
C12 C11 Br1 119.7(3) . . ?
C14 C13 H13 118.8 . . ?
C12 C13 C14 122.4(3) . . ?
C12 C13 H13 118.8 . . ?
N1 C1 H1 118.2 . . ?
N1 C1 C2 123.6(4) . . ?
C2 C1 H1 118.2 . . ?
C2 C3 H3 120.6 . . ?
C4 C3 H3 120.6 . . ?
C4 C3 C2 118.8(4) . . ?
C1 C2 C3 118.9(4) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 H2 120.6 . . ?
C5 C4 H4 119.8 . . ?
C3 C4 C5 120.4(4) . . ?
C3 C4 H4 119.8 . . ?

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
Cu1 O1 C14 C9 37.5(4) . . . . ?
Cu1 O1 C14 C13 -143.8(3) . . . . ?
Cu1 N2 C8 C9 -2.9(5) . . . . ?
Cu1 N2 C7 C6 -56.4(4) . . . . ?
Cu1 N1 C5 C6 -1.4(5) . . . . ?
Cu1 N1 C5 C4 178.5(3) . . . . ?
Cu1 N1 C1 C2 -178.1(3) . . . . ?
O1 C14 C9 C8 -5.5(5) . . . . ?
O1 C14 C9 C10 174.2(3) . . . . ?
O1 C14 C13 C12 -176.3(3) . . . . ?
N2 C8 C9 C14 -13.1(6) . . . . ?
N2 C8 C9 C10 167.2(3) . . . . ?
N2 C7 C6 C5 76.1(4) . . . . ?
N1 C5 C6 C7 -43.9(5) . . . . ?
N1 C5 C4 C3 0.3(6) . . . . ?
N1 C1 C2 C3 -1.0(7) . . . . ?
C8 N2 C7 C6 120.1(3) . . . . ?
C5 N1 C1 C2 1.9(6) . . . . ?
C9 C14 C13 C12 2.4(5) . . . . ?
C9 C10 C11 Br1 180.0(3) . . . . ?
C9 C10 C11 C12 0.6(5) . . . . ?
C7 N2 C8 C9 -179.2(3) . . . . ?
C6 C5 C4 C3 -179.9(4) . . . . ?
C11 C10 C9 C14 3.2(5) . . . . ?
C11 C10 C9 C8 -177.1(3) . . . . ?
C11 C12 C13 C14 1.2(6) . . . . ?
C13 C14 C9 C8 175.7(3) . . . . ?
C13 C14 C9 C10 -4.6(5) . . . . ?
C13 C12 C11 Br1 177.8(3) . . . . ?
C13 C12 C11 C10 -2.8(5) . . . . ?
C1 N1 C5 C6 178.6(3) . . . . ?
C1 N1 C5 C4 -1.5(5) . . . . ?
C2 C3 C4 C5 0.7(6) . . . . ?
C4 C5 C6 C7 136.2(4) . . . . ?
C4 C3 C2 C1 -0.4(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
