# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2515084'
loop_
_audit_author_name
_audit_author_address
'Thierry bateille'
;Rennes
France
;
_audit_update_record             
;
2025-12-11 deposited with the CCDC.	2026-05-12 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            'C10 H28 Br3 Cl N4'
_chemical_formula_weight         479.54

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'
Cl Cl 0.1484 0.1585 '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'

_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                   8.2340(16)
_cell_length_b                   9.7895(19)
_cell_length_c                   11.358(2)
_cell_angle_alpha                90
_cell_angle_beta                 107.528(7)
_cell_angle_gamma                90
_cell_volume                     873.0(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2017
_cell_measurement_theta_min      1.80

_cell_measurement_theta_max      28.39



_exptl_crystal_description       Plate

_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.824
_exptl_crystal_F_000             476
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    7.076
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CAD4 plate'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7490
_diffrn_reflns_av_unetI/netI     0.0450
_diffrn_reflns_av_R_equivalents  0.0469
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.707
_diffrn_reflns_theta_max         27.563
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2012
_reflns_number_gt                1772
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_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)+(0.0755P)²+4.8414P] 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         2012
_refine_ls_number_parameters     82
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0557
_refine_ls_R_factor_gt           0.0486
_refine_ls_wR_factor_ref         0.1423
_refine_ls_wR_factor_gt          0.1365
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_restrained_S_all      1.096
_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
N1 N 0.1045(5) 0.7829(3) 0.6301(3) 0.0071(7) Uani 1 1 d . . . . .
H1A H -0.007452 0.784311 0.584927 0.008 Uiso 1 1 calc R U . . .
H1B H 0.109479 0.786721 0.711161 0.008 Uiso 1 1 calc R U . . .
C2 C 0.1878(5) 0.9085(4) 0.5998(4) 0.0075(8) Uani 1 1 d . . . . .
H2A H 0.156377 0.987724 0.642571 0.009 Uiso 1 1 calc R U . . .
H2B H 0.143915 0.925545 0.509884 0.009 Uiso 1 1 calc R U . . .
C3 C 0.3820(6) 0.8970(5) 0.6374(4) 0.0107(8) Uani 1 1 d . . . . .
H3A H 0.431421 0.989134 0.659540 0.013 Uiso 1 1 calc R U . . .
H3B H 0.420574 0.839212 0.712199 0.013 Uiso 1 1 calc R U . . .
C4 C 0.4512(6) 0.8379(4) 0.5393(4) 0.0102(8) Uani 1 1 d . . . . .
H4A H 0.401411 0.888648 0.461345 0.012 Uiso 1 1 calc R U . . .
H4B H 0.575964 0.852081 0.564569 0.012 Uiso 1 1 calc R U . . .
N5 N 0.4152(5) 0.6885(4) 0.5152(3) 0.0099(7) Uani 1 1 d . . . . .
H5A H 0.480561 0.640879 0.581327 0.012 Uiso 1 1 calc R U . . .
H5B H 0.448761 0.664206 0.448733 0.012 Uiso 1 1 calc R U . . .
C6 C 0.2332(6) 0.6454(4) 0.4915(4) 0.0100(8) Uani 1 1 d . . . . .
H6A H 0.218578 0.551455 0.457566 0.012 Uiso 1 1 calc R U . . .
H6B H 0.158496 0.706668 0.428930 0.012 Uiso 1 1 calc R U . . .
C7 C 0.1793(6) 0.6491(4) 0.6073(4) 0.0094(8) Uani 1 1 d . . . . .
H7A H 0.094201 0.576131 0.602172 0.011 Uiso 1 1 calc R U . . .
H7B H 0.279617 0.628540 0.678931 0.011 Uiso 1 1 calc R U . . .
Cl1 Cl 0.26637(9) 0.78023(7) 0.92032(6) 0.0174(2) Uani 0.5 1 d . . P . .
Br1 Br 0.26637(9) 0.78023(7) 0.92032(6) 0.0174(2) Uani 0.5 1 d . . P . .
Br2 Br 0.63772(6) 0.51025(5) 0.74851(4) 0.0191(2) 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
N1 C2 1.497(5) . ?
N1 C7 1.503(5) . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
C2 C3 1.530(6) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.511(6) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 N5 1.500(6) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
N5 C6 1.502(6) . ?
N5 H5A 0.9100 . ?
N5 H5B 0.9100 . ?
C6 C7 1.510(6) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C7 115.9(3) . . ?
C2 N1 H1A 108.3 . . ?
C7 N1 H1A 108.3 . . ?
C2 N1 H1B 108.3 . . ?
C7 N1 H1B 108.3 . . ?
H1A N1 H1B 107.4 . . ?
N1 C2 C3 112.9(3) . . ?
N1 C2 H2A 109.0 . . ?
C3 C2 H2A 109.0 . . ?
N1 C2 H2B 109.0 . . ?
C3 C2 H2B 109.0 . . ?
H2A C2 H2B 107.8 . . ?
C4 C3 C2 114.6(4) . . ?
C4 C3 H3A 108.6 . . ?
C2 C3 H3A 108.6 . . ?
C4 C3 H3B 108.6 . . ?
C2 C3 H3B 108.6 . . ?
H3A C3 H3B 107.6 . . ?
N5 C4 C3 114.2(4) . . ?
N5 C4 H4A 108.7 . . ?
C3 C4 H4A 108.7 . . ?
N5 C4 H4B 108.7 . . ?
C3 C4 H4B 108.7 . . ?
H4A C4 H4B 107.6 . . ?
C4 N5 C6 116.0(3) . . ?
C4 N5 H5A 108.3 . . ?
C6 N5 H5A 108.3 . . ?
C4 N5 H5B 108.3 . . ?
C6 N5 H5B 108.3 . . ?
H5A N5 H5B 107.4 . . ?
N5 C6 C7 112.1(3) . . ?
N5 C6 H6A 109.2 . . ?
C7 C6 H6A 109.2 . . ?
N5 C6 H6B 109.2 . . ?
C7 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
N1 C7 C6 114.5(3) . . ?
N1 C7 H7A 108.6 . . ?
C6 C7 H7A 108.6 . . ?
N1 C7 H7B 108.6 . . ?
C6 C7 H7B 108.6 . . ?
H7A C7 H7B 107.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 N1 C2 C3 -40.2(5) . . . . ?
N1 C2 C3 C4 89.5(4) . . . . ?
C2 C3 C4 N5 -70.1(5) . . . . ?
C3 C4 N5 C6 50.9(5) . . . . ?
C4 N5 C6 C7 -72.2(5) . . . . ?
C2 N1 C7 C6 -39.1(5) . . . . ?
N5 C6 C7 N1 90.5(4) . . . . ?

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
N1 H1A Cl1 0.91 2.29 3.133(4) 153.0 4_575 yes
N1 H1B Cl1 0.91 2.34 3.162(4) 150.4 . yes
N1 H1B Br2 0.91 3.11 3.534(4) 110.2 2_556 yes
C2 H2A Br1 0.99 3.06 3.673(4) 121.0 2_556 yes
C2 H2A Br2 0.99 3.04 3.731(4) 127.9 2_556 yes
C2 H2B Br2 0.99 3.02 3.967(4) 160.5 4_575 yes
C3 H3B Br1 0.99 3.06 3.793(5) 132.2 . yes
C4 H4A Br2 0.99 2.89 3.827(4) 157.4 4_575 yes
C4 H4B Cl1 0.99 2.89 3.465(4) 117.7 4_675 yes
C4 H4B Br2 0.99 3.07 3.899(4) 141.7 2_656 yes
N5 H5A Br2 0.91 2.33 3.241(4) 177.1 . yes
N5 H5B Cl1 0.91 2.78 3.390(4) 125.1 4_675 yes
N5 H5B Br2 0.91 2.74 3.487(4) 140.7 3_666 yes
C6 H6A Cl1 0.99 2.98 3.712(4) 131.5 2_546 yes
C6 H6A Br2 0.99 2.99 3.553(4) 117.6 3_666 yes
C7 H7B Br2 0.99 3.04 3.876(4) 142.6 . yes

_refine_diff_density_max         1.753
_refine_diff_density_min         -1.354
_refine_diff_density_rms         0.200



