# Supplementary Information (SI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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. 
# 
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data_SM_33_0ma_a
_database_code_depnum_ccdc_archive 'CCDC 2355357'
loop_
_audit_author_name
_audit_author_address
'Muhammad Usman Anwar'
;University of Nizwa
Oman
;
_audit_update_record             
;
2024-12-09 deposited with the CCDC.	2025-05-01 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         'C23 H17 Br F N3 O3'
_chemical_formula_sum            'C23 H17 Br F N3 O3'
_chemical_formula_weight         482.30

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'
O O 0.0106 0.0060 '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'
F F 0.0171 0.0103 '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, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   11.9327(14)
_cell_length_b                   11.8361(13)
_cell_length_c                   29.118(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4112.5(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9905
_cell_measurement_theta_min      3.21
_cell_measurement_theta_max      24.77

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.558
_exptl_crystal_F_000             1952
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.80
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    2.039
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.4479
_exptl_absorpt_correction_T_max  0.7451
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(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            78208
_diffrn_reflns_av_unetI/netI     0.0248
_diffrn_reflns_av_R_equivalents  0.0798
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         3.207
_diffrn_reflns_theta_max         24.855
_diffrn_reflns_theta_full        24.855
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             3537
_reflns_number_gt                2632
_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 2018/2 (Sheldrick, 2018)'
_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)+(0.0505P)²+3.1090P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3537
_refine_ls_number_parameters     283
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0670
_refine_ls_R_factor_gt           0.0417
_refine_ls_wR_factor_ref         0.1100
_refine_ls_wR_factor_gt          0.0952
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_restrained_S_all      1.098
_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
Br1 Br -0.01039(4) 0.63178(4) 0.73175(2) 0.06734(18) Uani 1 1 d . . . . .
F2 F 0.90693(16) 0.80512(17) 0.34076(7) 0.0609(5) Uani 1 1 d . . . . .
O1 O -0.0777(2) 0.7382(2) 0.50348(8) 0.0631(7) Uani 1 1 d . . . . .
O2 O 0.26831(19) 0.50385(18) 0.49400(7) 0.0475(6) Uani 1 1 d . . . . .
O3 O 0.54961(17) 0.53730(19) 0.38344(7) 0.0453(5) Uani 1 1 d . . . . .
N1 N 0.0764(2) 0.6282(2) 0.49777(8) 0.0377(6) Uani 1 1 d D . . . .
H1 H 0.125(2) 0.587(2) 0.5090(10) 0.045 Uiso 1 1 d D U . . .
N2 N 0.0817(2) 0.64080(19) 0.45130(8) 0.0348(6) Uani 1 1 d . . . . .
N3 N 0.3251(2) 0.48947(19) 0.41844(8) 0.0350(6) Uani 1 1 d . . . . .
C1 C -0.0118(2) 0.6367(2) 0.66711(10) 0.0376(7) Uani 1 1 d . . . . .
C2 C -0.0956(3) 0.6957(3) 0.64494(11) 0.0433(8) Uani 1 1 d . . . . .
H2 H -0.153305 0.728844 0.661659 0.052 Uiso 1 1 calc R U . . .
C3 C -0.0929(3) 0.7051(3) 0.59787(11) 0.0394(7) Uani 1 1 d . . . . .
H3 H -0.149580 0.744485 0.582926 0.047 Uiso 1 1 calc R U . . .
C4 C -0.0075(2) 0.6570(2) 0.57228(10) 0.0308(6) Uani 1 1 d . . . . .
C5 C 0.0743(3) 0.5948(3) 0.59516(11) 0.0404(7) Uani 1 1 d . . . . .
H5 H 0.130832 0.559734 0.578434 0.049 Uiso 1 1 calc R U . . .
C6 C 0.0724(3) 0.5845(3) 0.64231(11) 0.0440(8) Uani 1 1 d . . . . .
H6 H 0.127377 0.542854 0.657336 0.053 Uiso 1 1 calc R U . . .
C7 C -0.0084(2) 0.6782(3) 0.52178(10) 0.0357(7) Uani 1 1 d . . . . .
C8 C 0.1648(2) 0.5917(2) 0.43101(9) 0.0306(6) Uani 1 1 d . . . . .
C9 C 0.2568(2) 0.5245(2) 0.45296(10) 0.0352(7) Uani 1 1 d . . . . .
C10 C 0.1867(2) 0.5900(2) 0.38216(9) 0.0321(6) Uani 1 1 d . . . . .
C11 C 0.1304(3) 0.6357(3) 0.34510(10) 0.0412(7) Uani 1 1 d . . . . .
H11 H 0.065917 0.678585 0.349244 0.049 Uiso 1 1 calc R U . . .
C12 C 0.1727(3) 0.6160(3) 0.30185(11) 0.0495(8) Uani 1 1 d . . . . .
H12 H 0.136662 0.646775 0.276441 0.059 Uiso 1 1 calc R U . . .
C13 C 0.2673(3) 0.5513(3) 0.29564(10) 0.0488(8) Uani 1 1 d . . . . .
H13 H 0.293029 0.538088 0.265983 0.059 Uiso 1 1 calc R U . . .
C14 C 0.3252(3) 0.5055(3) 0.33239(10) 0.0420(7) Uani 1 1 d . . . . .
H14 H 0.389324 0.462173 0.328081 0.050 Uiso 1 1 calc R U . . .
C15 C 0.2835(2) 0.5271(2) 0.37565(9) 0.0324(6) Uani 1 1 d . . . . .
C16 C 0.4264(3) 0.4236(3) 0.42630(11) 0.0414(7) Uani 1 1 d . . . . .
H16A H 0.434481 0.368796 0.401762 0.050 Uiso 1 1 calc R U . . .
H16B H 0.418576 0.382334 0.454897 0.050 Uiso 1 1 calc R U . . .
C17 C 0.5303(3) 0.4944(3) 0.42854(11) 0.0430(8) Uani 1 1 d . . . . .
H17A H 0.520220 0.556054 0.450086 0.052 Uiso 1 1 calc R U . . .
H17B H 0.593442 0.449048 0.438533 0.052 Uiso 1 1 calc R U . . .
C18 C 0.6429(2) 0.6015(2) 0.37565(10) 0.0353(7) Uani 1 1 d . . . . .
C19 C 0.6602(3) 0.6326(3) 0.33054(10) 0.0441(8) Uani 1 1 d . . . . .
H19 H 0.611080 0.607444 0.307957 0.053 Uiso 1 1 calc R U . . .
C20 C 0.7489(3) 0.7000(3) 0.31854(10) 0.0438(8) Uani 1 1 d . . . . .
H20 H 0.760652 0.720643 0.288108 0.053 Uiso 1 1 calc R U . . .
C21 C 0.8199(2) 0.7361(3) 0.35248(11) 0.0410(7) Uani 1 1 d . . . . .
C22 C 0.8065(3) 0.7058(3) 0.39733(11) 0.0433(8) Uani 1 1 d . . . . .
H22 H 0.856947 0.730251 0.419564 0.052 Uiso 1 1 calc R U . . .
C23 C 0.7165(3) 0.6380(3) 0.40916(10) 0.0399(7) Uani 1 1 d . . . . .
H23 H 0.705566 0.617019 0.439610 0.048 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 1.883(3) . ?
F2 C21 1.364(3) . ?
O1 C7 1.213(4) . ?
O2 C9 1.227(3) . ?
O3 C18 1.366(3) . ?
O3 C17 1.427(4) . ?
N1 N2 1.363(3) . ?
N1 C7 1.365(4) . ?
N1 H1 0.825(18) . ?
N2 C8 1.292(4) . ?
N3 C9 1.359(4) . ?
N3 C15 1.413(3) . ?
N3 C16 1.456(4) . ?
C1 C2 1.380(4) . ?
C1 C6 1.383(4) . ?
C2 C3 1.375(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.385(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.392(4) . ?
C4 C7 1.492(4) . ?
C5 C6 1.379(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C8 C10 1.446(4) . ?
C8 C9 1.499(4) . ?
C10 C11 1.381(4) . ?
C10 C15 1.388(4) . ?
C11 C12 1.376(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.376(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.384(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.378(4) . ?
C14 H14 0.9300 . ?
C16 C17 1.497(4) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.380(4) . ?
C18 C23 1.382(4) . ?
C19 C20 1.371(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.370(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.364(4) . ?
C22 C23 1.385(4) . ?
C22 H22 0.9300 . ?
C23 H23 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
C18 O3 C17 118.9(2) . . ?
N2 N1 C7 119.7(2) . . ?
N2 N1 H1 115(2) . . ?
C7 N1 H1 125(2) . . ?
C8 N2 N1 116.1(2) . . ?
C9 N3 C15 110.2(2) . . ?
C9 N3 C16 123.0(2) . . ?
C15 N3 C16 126.8(2) . . ?
C2 C1 C6 120.6(3) . . ?
C2 C1 Br1 119.3(2) . . ?
C6 C1 Br1 120.1(2) . . ?
C3 C2 C1 119.3(3) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C2 C3 C4 121.4(3) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C3 C4 C5 118.4(3) . . ?
C3 C4 C7 117.1(3) . . ?
C5 C4 C7 124.5(3) . . ?
C6 C5 C4 120.8(3) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C5 C6 C1 119.5(3) . . ?
C5 C6 H6 120.3 . . ?
C1 C6 H6 120.3 . . ?
O1 C7 N1 122.3(3) . . ?
O1 C7 C4 122.5(3) . . ?
N1 C7 C4 115.2(3) . . ?
N2 C8 C10 126.5(3) . . ?
N2 C8 C9 127.3(3) . . ?
C10 C8 C9 106.3(2) . . ?
O2 C9 N3 126.3(3) . . ?
O2 C9 C8 127.0(3) . . ?
N3 C9 C8 106.6(2) . . ?
C11 C10 C15 120.5(3) . . ?
C11 C10 C8 132.5(3) . . ?
C15 C10 C8 107.0(2) . . ?
C12 C11 C10 118.1(3) . . ?
C12 C11 H11 121.0 . . ?
C10 C11 H11 121.0 . . ?
C13 C12 C11 121.0(3) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C12 C13 C14 121.7(3) . . ?
C12 C13 H13 119.1 . . ?
C14 C13 H13 119.1 . . ?
C15 C14 C13 117.0(3) . . ?
C15 C14 H14 121.5 . . ?
C13 C14 H14 121.5 . . ?
C14 C15 C10 121.6(3) . . ?
C14 C15 N3 128.4(3) . . ?
C10 C15 N3 110.0(2) . . ?
N3 C16 C17 113.2(2) . . ?
N3 C16 H16A 108.9 . . ?
C17 C16 H16A 108.9 . . ?
N3 C16 H16B 108.9 . . ?
C17 C16 H16B 108.9 . . ?
H16A C16 H16B 107.7 . . ?
O3 C17 C16 107.0(3) . . ?
O3 C17 H17A 110.3 . . ?
C16 C17 H17A 110.3 . . ?
O3 C17 H17B 110.3 . . ?
C16 C17 H17B 110.3 . . ?
H17A C17 H17B 108.6 . . ?
O3 C18 C19 115.4(3) . . ?
O3 C18 C23 125.0(3) . . ?
C19 C18 C23 119.6(3) . . ?
C20 C19 C18 120.9(3) . . ?
C20 C19 H19 119.5 . . ?
C18 C19 H19 119.5 . . ?
C21 C20 C19 118.4(3) . . ?
C21 C20 H20 120.8 . . ?
C19 C20 H20 120.8 . . ?
C22 C21 F2 119.1(3) . . ?
C22 C21 C20 122.4(3) . . ?
F2 C21 C20 118.5(3) . . ?
C21 C22 C23 118.8(3) . . ?
C21 C22 H22 120.6 . . ?
C23 C22 H22 120.6 . . ?
C18 C23 C22 119.9(3) . . ?
C18 C23 H23 120.0 . . ?
C22 C23 H23 120.0 . . ?

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 N2 C8 179.5(3) . . . . ?
C6 C1 C2 C3 -1.9(4) . . . . ?
Br1 C1 C2 C3 176.1(2) . . . . ?
C1 C2 C3 C4 -0.4(5) . . . . ?
C2 C3 C4 C5 2.3(4) . . . . ?
C2 C3 C4 C7 -176.2(3) . . . . ?
C3 C4 C5 C6 -2.2(4) . . . . ?
C7 C4 C5 C6 176.3(3) . . . . ?
C4 C5 C6 C1 0.0(5) . . . . ?
C2 C1 C6 C5 2.0(5) . . . . ?
Br1 C1 C6 C5 -175.9(2) . . . . ?
N2 N1 C7 O1 -3.3(5) . . . . ?
N2 N1 C7 C4 178.8(2) . . . . ?
C3 C4 C7 O1 2.8(4) . . . . ?
C5 C4 C7 O1 -175.7(3) . . . . ?
C3 C4 C7 N1 -179.3(3) . . . . ?
C5 C4 C7 N1 2.3(4) . . . . ?
N1 N2 C8 C10 178.2(3) . . . . ?
N1 N2 C8 C9 -1.2(4) . . . . ?
C15 N3 C9 O2 178.4(3) . . . . ?
C16 N3 C9 O2 -2.2(5) . . . . ?
C15 N3 C9 C8 -1.0(3) . . . . ?
C16 N3 C9 C8 178.5(2) . . . . ?
N2 C8 C9 O2 0.7(5) . . . . ?
C10 C8 C9 O2 -178.8(3) . . . . ?
N2 C8 C9 N3 -179.9(3) . . . . ?
C10 C8 C9 N3 0.6(3) . . . . ?
N2 C8 C10 C11 -0.4(5) . . . . ?
C9 C8 C10 C11 179.1(3) . . . . ?
N2 C8 C10 C15 -179.5(3) . . . . ?
C9 C8 C10 C15 0.0(3) . . . . ?
C15 C10 C11 C12 0.6(4) . . . . ?
C8 C10 C11 C12 -178.3(3) . . . . ?
C10 C11 C12 C13 0.8(5) . . . . ?
C11 C12 C13 C14 -1.3(5) . . . . ?
C12 C13 C14 C15 0.3(5) . . . . ?
C13 C14 C15 C10 1.2(4) . . . . ?
C13 C14 C15 N3 179.0(3) . . . . ?
C11 C10 C15 C14 -1.7(4) . . . . ?
C8 C10 C15 C14 177.5(3) . . . . ?
C11 C10 C15 N3 -179.8(3) . . . . ?
C8 C10 C15 N3 -0.6(3) . . . . ?
C9 N3 C15 C14 -176.9(3) . . . . ?
C16 N3 C15 C14 3.7(5) . . . . ?
C9 N3 C15 C10 1.1(3) . . . . ?
C16 N3 C15 C10 -178.3(3) . . . . ?
C9 N3 C16 C17 -95.8(3) . . . . ?
C15 N3 C16 C17 83.5(4) . . . . ?
C18 O3 C17 C16 -177.4(2) . . . . ?
N3 C16 C17 O3 -68.9(3) . . . . ?
C17 O3 C18 C19 175.2(3) . . . . ?
C17 O3 C18 C23 -6.4(4) . . . . ?
O3 C18 C19 C20 177.9(3) . . . . ?
C23 C18 C19 C20 -0.6(5) . . . . ?
C18 C19 C20 C21 -0.2(5) . . . . ?
C19 C20 C21 C22 1.2(5) . . . . ?
C19 C20 C21 F2 -178.7(3) . . . . ?
F2 C21 C22 C23 178.5(3) . . . . ?
C20 C21 C22 C23 -1.4(5) . . . . ?
O3 C18 C23 C22 -178.0(3) . . . . ?
C19 C18 C23 C22 0.4(4) . . . . ?
C21 C22 C23 C18 0.6(4) . . . . ?

_refine_diff_density_max         0.210
_refine_diff_density_min         -0.577
_refine_diff_density_rms         0.067



