# Supplementary Information (SI) 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_arb208_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2301303'
loop_
_audit_author_name
_audit_author_address
'Muhammed Yousufuddin'
;University of North Texas at Dallas
United States of America
;
_audit_update_record             
;
2023-10-14 deposited with the CCDC.	2024-08-01 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         'C16 H13 Br2 N O2'
_chemical_formula_sum            'C16 H13 Br2 N O2'
_chemical_formula_weight         411.09

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'

_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                   9.9175(14)
_cell_length_b                   17.323(3)
_cell_length_c                   10.7669(15)
_cell_angle_alpha                90
_cell_angle_beta                 115.609(2)
_cell_angle_gamma                90
_cell_volume                     1668.1(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4047
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      22.59

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.637
_exptl_crystal_F_000             808
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    4.862
_shelx_estimated_absorpt_T_min   0.323
_shelx_estimated_absorpt_T_max   0.793
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.441
_exptl_absorpt_correction_T_max  0.745
_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            18321
_diffrn_reflns_av_unetI/netI     0.0352
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.336
_diffrn_reflns_theta_max         29.146
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4466
_reflns_number_gt                2755
_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 2014/4 (Sheldrick, 2014)'
_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)+(0.0500P)²+1.3201P] 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         4466
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0852
_refine_ls_R_factor_gt           0.0442
_refine_ls_wR_factor_ref         0.1234
_refine_ls_wR_factor_gt          0.1051
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_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
Br1 Br 0.77143(5) 0.09896(3) 0.30782(5) 0.08462(19) Uani 1 1 d . . . . .
Br2 Br 0.70147(5) 0.04921(3) 0.55557(6) 0.08555(19) Uani 1 1 d . . . . .
O1 O 0.9537(3) 0.20267(19) 0.6164(3) 0.0784(8) Uani 1 1 d . . . . .
O2 O 0.7070(3) 0.32534(14) 0.5095(3) 0.0637(7) Uani 1 1 d . . . . .
N1 N 0.7126(3) 0.24857(17) 0.4797(3) 0.0574(7) Uani 1 1 d . . . . .
C1 C 0.7183(3) 0.1338(2) 0.4502(3) 0.0499(7) Uani 1 1 d . . . . .
C2 C 0.8248(4) 0.1980(2) 0.5355(4) 0.0539(8) Uani 1 1 d . . . . .
C3 C 0.5904(4) 0.19525(19) 0.4015(3) 0.0475(7) Uani 1 1 d . . . . .
H3 H 0.549541 0.204593 0.302137 0.057 Uiso 1 1 calc R U . . .
C4 C 0.7352(6) 0.3744(2) 0.4137(4) 0.0748(12) Uani 1 1 d . . . . .
H4A H 0.656159 0.368705 0.321282 0.090 Uiso 1 1 calc R U . . .
H4B H 0.829706 0.360982 0.412744 0.090 Uiso 1 1 calc R U . . .
C5 C 0.7397(4) 0.4546(2) 0.4634(4) 0.0549(8) Uani 1 1 d . . . . .
C6 C 0.8668(5) 0.4823(3) 0.5697(4) 0.0713(11) Uani 1 1 d . . . . .
H6 H 0.950832 0.450825 0.608525 0.086 Uiso 1 1 calc R U . . .
C7 C 0.8718(7) 0.5550(3) 0.6191(6) 0.0977(16) Uani 1 1 d . . . . .
H7 H 0.959925 0.572774 0.690146 0.117 Uiso 1 1 calc R U . . .
C8 C 0.7515(8) 0.6018(3) 0.5671(6) 0.0974(17) Uani 1 1 d . . . . .
H8 H 0.755870 0.650939 0.603460 0.117 Uiso 1 1 calc R U . . .
C9 C 0.6236(7) 0.5766(3) 0.4609(6) 0.0915(15) Uani 1 1 d . . . . .
H9 H 0.540793 0.608983 0.423044 0.110 Uiso 1 1 calc R U . . .
C10 C 0.6168(5) 0.5027(3) 0.4093(4) 0.0735(11) Uani 1 1 d . . . . .
H10 H 0.528852 0.485401 0.337638 0.088 Uiso 1 1 calc R U . . .
C11 C 0.4698(3) 0.18991(18) 0.4496(3) 0.0456(7) Uani 1 1 d . . . . .
C12 C 0.4951(4) 0.2121(2) 0.5814(4) 0.0592(9) Uani 1 1 d . . . . .
H12 H 0.588515 0.230744 0.641804 0.071 Uiso 1 1 calc R U . . .
C13 C 0.3829(6) 0.2066(3) 0.6235(5) 0.0764(12) Uani 1 1 d . . . . .
H13 H 0.400287 0.222019 0.711858 0.092 Uiso 1 1 calc R U . . .
C14 C 0.2448(5) 0.1784(3) 0.5350(6) 0.0850(14) Uani 1 1 d . . . . .
H14 H 0.168840 0.174752 0.563497 0.102 Uiso 1 1 calc R U . . .
C15 C 0.2197(5) 0.1559(3) 0.4056(5) 0.0798(13) Uani 1 1 d . . . . .
H15 H 0.126786 0.136164 0.346216 0.096 Uiso 1 1 calc R U . . .
C16 C 0.3308(4) 0.1620(2) 0.3622(4) 0.0609(9) Uani 1 1 d . . . . .
H16 H 0.312025 0.147257 0.273199 0.073 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 1.922(3) . ?
Br2 C1 1.904(3) . ?
O1 C2 1.199(4) . ?
O2 N1 1.375(4) . ?
O2 C4 1.454(5) . ?
N1 C2 1.337(5) . ?
N1 C3 1.466(4) . ?
C1 C2 1.536(5) . ?
C1 C3 1.562(5) . ?
C3 C11 1.498(4) . ?
C3 H3 0.9800 . ?
C4 C5 1.482(5) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.372(5) . ?
C5 C10 1.380(6) . ?
C6 C7 1.361(7) . ?
C6 H6 0.9300 . ?
C7 C8 1.348(8) . ?
C7 H7 0.9300 . ?
C8 C9 1.361(8) . ?
C8 H8 0.9300 . ?
C9 C10 1.386(7) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C16 1.377(5) . ?
C11 C12 1.385(5) . ?
C12 C13 1.374(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.376(7) . ?
C13 H13 0.9300 . ?
C14 C15 1.363(7) . ?
C14 H14 0.9300 . ?
C15 C16 1.374(6) . ?
C15 H15 0.9300 . ?
C16 H16 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
N1 O2 C4 111.1(3) . . ?
C2 N1 O2 129.6(3) . . ?
C2 N1 C3 99.6(3) . . ?
O2 N1 C3 129.6(3) . . ?
C2 C1 C3 87.5(2) . . ?
C2 C1 Br2 114.6(2) . . ?
C3 C1 Br2 117.2(2) . . ?
C2 C1 Br1 110.5(2) . . ?
C3 C1 Br1 114.1(2) . . ?
Br2 C1 Br1 111.00(17) . . ?
O1 C2 N1 134.6(4) . . ?
O1 C2 C1 136.5(4) . . ?
N1 C2 C1 89.0(3) . . ?
N1 C3 C11 115.2(3) . . ?
N1 C3 C1 83.5(2) . . ?
C11 C3 C1 119.7(3) . . ?
N1 C3 H3 111.8 . . ?
C11 C3 H3 111.8 . . ?
C1 C3 H3 111.8 . . ?
O2 C4 C5 106.0(3) . . ?
O2 C4 H4A 110.5 . . ?
C5 C4 H4A 110.5 . . ?
O2 C4 H4B 110.5 . . ?
C5 C4 H4B 110.5 . . ?
H4A C4 H4B 108.7 . . ?
C6 C5 C10 117.8(4) . . ?
C6 C5 C4 120.1(4) . . ?
C10 C5 C4 122.1(4) . . ?
C7 C6 C5 121.0(5) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C8 C7 C6 121.2(5) . . ?
C8 C7 H7 119.4 . . ?
C6 C7 H7 119.4 . . ?
C7 C8 C9 119.5(5) . . ?
C7 C8 H8 120.2 . . ?
C9 C8 H8 120.2 . . ?
C8 C9 C10 119.9(5) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?
C5 C10 C9 120.6(4) . . ?
C5 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C16 C11 C12 118.8(3) . . ?
C16 C11 C3 119.9(3) . . ?
C12 C11 C3 121.3(3) . . ?
C13 C12 C11 120.3(4) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C12 C13 C14 120.1(4) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C15 C14 C13 119.8(4) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C14 C15 C16 120.4(4) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C15 C16 C11 120.6(4) . . ?
C15 C16 H16 119.7 . . ?
C11 C16 H16 119.7 . . ?

_refine_diff_density_max         0.798
_refine_diff_density_min         -0.763
_refine_diff_density_rms         0.068



####################################################################### 
# 
# 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_arc77_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2301304'
loop_
_audit_author_name
_audit_author_address
'Muhammed Yousufuddin'
;University of North Texas at Dallas
United States of America
;
_audit_update_record             
;
2023-10-14 deposited with the CCDC.	2024-08-01 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         'C16 H13 Br Cl N O2'
_chemical_formula_sum            'C16 H13 Br Cl N O2'
_chemical_formula_weight         366.63

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'
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                   9.915(3)
_cell_length_b                   17.251(6)
_cell_length_c                   10.682(3)
_cell_angle_alpha                90
_cell_angle_beta                 115.375(5)
_cell_angle_gamma                90
_cell_volume                     1650.8(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4625
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      23.52

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_F_000             736
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    2.654
_shelx_estimated_absorpt_T_min   0.619
_shelx_estimated_absorpt_T_max   0.777
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.602
_exptl_absorpt_correction_T_max  0.746
_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            20864
_diffrn_reflns_av_unetI/netI     0.0379
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.347
_diffrn_reflns_theta_max         31.775
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5570
_reflns_number_gt                2956
_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 2014/4 (Sheldrick, 2014)'
_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)+(0.0668P)²+0.4672P] 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         5570
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0992
_refine_ls_R_factor_gt           0.0476
_refine_ls_wR_factor_ref         0.1519
_refine_ls_wR_factor_gt          0.1286
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_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
Br1 Br 0.22694(4) 0.09039(2) 0.67437(4) 0.09105(18) Uani 1 1 d . . . . .
Cl1 Cl 0.30189(10) 0.05419(5) 0.43342(11) 0.0862(3) Uani 1 1 d . . . . .
O1 O 0.0485(2) 0.20018(15) 0.3689(2) 0.0862(7) Uani 1 1 d . . . . .
O2 O 0.2927(2) 0.32350(10) 0.4845(2) 0.0662(5) Uani 1 1 d . . . . .
N1 N 0.2872(2) 0.24565(12) 0.5105(2) 0.0612(5) Uani 1 1 d . . . . .
C1 C 0.2822(3) 0.12987(15) 0.5337(3) 0.0542(6) Uani 1 1 d . . . . .
C2 C 0.1769(3) 0.19514(16) 0.4513(3) 0.0585(6) Uani 1 1 d . . . . .
C3 C 0.4103(3) 0.19183(14) 0.5881(3) 0.0508(5) Uani 1 1 d . . . . .
H3 H 0.449969 0.199451 0.688494 0.061 Uiso 1 1 calc R U . . .
C4 C 0.5309(3) 0.18776(13) 0.5398(2) 0.0497(5) Uani 1 1 d . . . . .
C5 C 0.5086(3) 0.21312(16) 0.4093(3) 0.0626(6) Uani 1 1 d . . . . .
H5 H 0.416582 0.233546 0.349551 0.075 Uiso 1 1 calc R U . . .
C6 C 0.6217(5) 0.2083(2) 0.3673(4) 0.0820(9) Uani 1 1 d . . . . .
H6 H 0.605778 0.225782 0.279699 0.098 Uiso 1 1 calc R U . . .
C7 C 0.7568(4) 0.1781(2) 0.4533(5) 0.0908(11) Uani 1 1 d . . . . .
H7 H 0.832751 0.174870 0.424348 0.109 Uiso 1 1 calc R U . . .
C8 C 0.7807(4) 0.1524(2) 0.5829(4) 0.0891(10) Uani 1 1 d . . . . .
H8 H 0.872833 0.131510 0.641138 0.107 Uiso 1 1 calc R U . . .
C9 C 0.6689(3) 0.15739(18) 0.6278(3) 0.0664(7) Uani 1 1 d . . . . .
H9 H 0.686222 0.140519 0.716067 0.080 Uiso 1 1 calc R U . . .
C10 C 0.2587(4) 0.37046(17) 0.5809(3) 0.0745(8) Uani 1 1 d . . . . .
H10A H 0.333778 0.363083 0.675089 0.089 Uiso 1 1 calc R U . . .
H10B H 0.161911 0.356621 0.576533 0.089 Uiso 1 1 calc R U . . .
C11 C 0.2584(3) 0.45216(15) 0.5362(3) 0.0576(6) Uani 1 1 d . . . . .
C12 C 0.3829(4) 0.4992(2) 0.5946(3) 0.0784(9) Uani 1 1 d . . . . .
H12 H 0.469418 0.480427 0.666405 0.094 Uiso 1 1 calc R U . . .
C13 C 0.3793(6) 0.5744(2) 0.5465(5) 0.0984(12) Uani 1 1 d . . . . .
H13 H 0.463209 0.605900 0.586160 0.118 Uiso 1 1 calc R U . . .
C14 C 0.2528(6) 0.6019(2) 0.4411(5) 0.1019(13) Uani 1 1 d . . . . .
H14 H 0.250625 0.652091 0.408629 0.122 Uiso 1 1 calc R U . . .
C15 C 0.1307(6) 0.5565(2) 0.3838(4) 0.1014(13) Uani 1 1 d . . . . .
H15 H 0.044443 0.575733 0.312375 0.122 Uiso 1 1 calc R U . . .
C16 C 0.1326(4) 0.48212(19) 0.4299(3) 0.0759(8) Uani 1 1 d . . . . .
H16 H 0.047709 0.451448 0.388832 0.091 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 1.930(3) . ?
Cl1 C1 1.752(3) . ?
O1 C2 1.202(3) . ?
O2 N1 1.377(3) . ?
O2 C10 1.459(3) . ?
N1 C2 1.327(3) . ?
N1 C3 1.474(3) . ?
C1 C2 1.531(4) . ?
C1 C3 1.569(3) . ?
C3 C4 1.493(3) . ?
C3 H3 0.9800 . ?
C4 C5 1.386(4) . ?
C4 C9 1.389(4) . ?
C5 C6 1.377(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.362(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.374(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.386(5) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 C11 1.488(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C16 1.378(4) . ?
C11 C12 1.382(4) . ?
C12 C13 1.391(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.362(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.349(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.371(5) . ?
C15 H15 0.9300 . ?
C16 H16 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
N1 O2 C10 111.0(2) . . ?
C2 N1 O2 129.8(2) . . ?
C2 N1 C3 99.7(2) . . ?
O2 N1 C3 129.3(2) . . ?
C2 C1 C3 87.47(19) . . ?
C2 C1 Cl1 115.06(19) . . ?
C3 C1 Cl1 116.70(17) . . ?
C2 C1 Br1 110.87(17) . . ?
C3 C1 Br1 114.01(17) . . ?
Cl1 C1 Br1 110.87(14) . . ?
O1 C2 N1 134.4(3) . . ?
O1 C2 C1 136.2(3) . . ?
N1 C2 C1 89.4(2) . . ?
N1 C3 C4 115.3(2) . . ?
N1 C3 C1 82.95(18) . . ?
C4 C3 C1 118.8(2) . . ?
N1 C3 H3 112.2 . . ?
C4 C3 H3 112.2 . . ?
C1 C3 H3 112.2 . . ?
C5 C4 C9 119.1(3) . . ?
C5 C4 C3 121.8(2) . . ?
C9 C4 C3 119.1(2) . . ?
C6 C5 C4 120.5(3) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C7 C6 C5 120.4(3) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C6 C7 C8 119.9(3) . . ?
C6 C7 H7 120.1 . . ?
C8 C7 H7 120.1 . . ?
C7 C8 C9 120.7(3) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 H8 119.6 . . ?
C8 C9 C4 119.4(3) . . ?
C8 C9 H9 120.3 . . ?
C4 C9 H9 120.3 . . ?
O2 C10 C11 105.6(2) . . ?
O2 C10 H10A 110.6 . . ?
C11 C10 H10A 110.6 . . ?
O2 C10 H10B 110.6 . . ?
C11 C10 H10B 110.6 . . ?
H10A C10 H10B 108.8 . . ?
C16 C11 C12 118.0(3) . . ?
C16 C11 C10 119.8(3) . . ?
C12 C11 C10 122.2(3) . . ?
C11 C12 C13 120.3(3) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C14 C13 C12 119.9(4) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C15 C14 C13 120.2(4) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C14 C15 C16 120.6(4) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C15 C16 C11 121.0(4) . . ?
C15 C16 H16 119.5 . . ?
C11 C16 H16 119.5 . . ?

_refine_diff_density_max         0.745
_refine_diff_density_min         -0.663
_refine_diff_density_rms         0.054



####################################################################### 
# 
# 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_arc40f2_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2302628'
loop_
_audit_author_name
_audit_author_address
'Muhammed Yousufuddin' 'University of North Texas at Dallas'
_audit_update_record             
;
2023-10-22 deposited with the CCDC.	2024-08-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H10 Br N O2'
_chemical_formula_sum            'C10 H10 Br N O2'
_chemical_formula_weight         256.10

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_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'

_cell_length_a                   5.6110(6)
_cell_length_b                   7.1772(8)
_cell_length_c                   25.602(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1031.0(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4497
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      27.01

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.650
_exptl_crystal_F_000             512
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    3.959
_shelx_estimated_absorpt_T_min   0.505
_shelx_estimated_absorpt_T_max   0.693
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.546
_exptl_absorpt_correction_T_max  0.741
_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            13720
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_av_R_equivalents  0.0290
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_theta_min         2.948
_diffrn_reflns_theta_max         31.875
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3540
_reflns_number_gt                2694
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.701
_reflns_Friedel_fraction_max     0.990
_reflns_Friedel_fraction_full    1.000

_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. Completness statistics refer to single and 
 composite reflections containing twin component 1 only. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Refined as a 2-component inversion twin. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0431P)²+0.1953P] 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_abs_structure_details 
; 
 Refined as an inversion twin. 
;
_refine_ls_abs_structure_Flack   0.272(14)
_chemical_absolute_configuration .
_refine_ls_number_reflns         3540
_refine_ls_number_parameters     129
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0547
_refine_ls_R_factor_gt           0.0360
_refine_ls_wR_factor_ref         0.0873
_refine_ls_wR_factor_gt          0.0807
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.013
_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
Br1 Br 0.20109(9) 1.05021(6) 0.38153(2) 0.06175(15) Uani 1 1 d . . . . .
O1 O 0.6339(6) 0.8912(4) 0.47181(12) 0.0662(8) Uani 1 1 d . . . . .
O2 O 0.7023(5) 0.5146(4) 0.41552(10) 0.0576(7) Uani 1 1 d . . . . .
N1 N 0.5240(5) 0.6449(4) 0.41657(11) 0.0438(6) Uani 1 1 d . . . . .
C1 C 0.5044(7) 0.8069(5) 0.44299(12) 0.0440(7) Uani 1 1 d . . . . .
C2 C 0.2502(6) 0.8278(5) 0.42213(12) 0.0429(7) Uani 1 1 d . . . . .
H2 H 0.131661 0.815848 0.450046 0.051 Uiso 1 1 calc R U . . .
C3 C 0.2871(6) 0.6396(5) 0.39241(11) 0.0389(6) Uani 1 1 d . . . . .
H3 H 0.188979 0.540271 0.407515 0.047 Uiso 1 1 calc R U . . .
C4 C 0.2805(6) 0.6341(4) 0.33353(11) 0.0341(6) Uani 1 1 d . . . . .
C5 C 0.4634(5) 0.7105(5) 0.30399(13) 0.0376(6) Uani 1 1 d . . . . .
H5 H 0.595510 0.762048 0.320488 0.045 Uiso 1 1 calc R U . . .
C6 C 0.4497(6) 0.7100(5) 0.25023(13) 0.0397(7) Uani 1 1 d . . . . .
H6 H 0.572011 0.762030 0.230540 0.048 Uiso 1 1 calc R U . . .
C7 C 0.2541(5) 0.6320(4) 0.22547(12) 0.0390(7) Uani 1 1 d . . . . .
H7 H 0.244889 0.632308 0.189204 0.047 Uiso 1 1 calc R U . . .
C8 C 0.0732(5) 0.5542(5) 0.25458(13) 0.0412(6) Uani 1 1 d . . . . .
H8 H -0.057921 0.501278 0.238023 0.049 Uiso 1 1 calc R U . . .
C9 C 0.0872(5) 0.5550(5) 0.30864(12) 0.0383(6) Uani 1 1 d . . . . .
H9 H -0.034503 0.501809 0.328280 0.046 Uiso 1 1 calc R U . . .
C10 C 0.6678(10) 0.3740(6) 0.45363(17) 0.0653(11) Uani 1 1 d . . . . .
H10A H 0.713967 0.420545 0.487295 0.098 Uiso 1 1 calc R U . . .
H10B H 0.763226 0.267327 0.445012 0.098 Uiso 1 1 calc R U . . .
H10C H 0.502729 0.338810 0.454415 0.098 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 C2 1.925(3) . ?
O1 C1 1.199(4) . ?
O2 N1 1.369(4) . ?
O2 C10 1.417(5) . ?
N1 C1 1.350(5) . ?
N1 C3 1.466(4) . ?
C1 C2 1.531(5) . ?
C2 C3 1.564(5) . ?
C2 H2 0.9800 . ?
C3 C4 1.508(4) . ?
C3 H3 0.9800 . ?
C4 C9 1.380(4) . ?
C4 C5 1.388(4) . ?
C5 C6 1.378(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.385(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.378(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.386(4) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?

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
N1 O2 C10 111.9(3) . . ?
C1 N1 O2 131.1(3) . . ?
C1 N1 C3 99.2(3) . . ?
O2 N1 C3 129.5(3) . . ?
O1 C1 N1 133.9(4) . . ?
O1 C1 C2 136.9(4) . . ?
N1 C1 C2 89.2(3) . . ?
C1 C2 C3 87.8(3) . . ?
C1 C2 Br1 113.8(2) . . ?
C3 C2 Br1 118.2(2) . . ?
C1 C2 H2 111.7 . . ?
C3 C2 H2 111.7 . . ?
Br1 C2 H2 111.7 . . ?
N1 C3 C4 116.4(3) . . ?
N1 C3 C2 83.8(2) . . ?
C4 C3 C2 120.3(3) . . ?
N1 C3 H3 111.2 . . ?
C4 C3 H3 111.2 . . ?
C2 C3 H3 111.2 . . ?
C9 C4 C5 119.5(3) . . ?
C9 C4 C3 119.4(3) . . ?
C5 C4 C3 121.1(3) . . ?
C6 C5 C4 120.1(3) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C7 120.1(3) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C8 C7 C6 120.0(3) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C7 C8 C9 119.8(3) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
C4 C9 C8 120.5(3) . . ?
C4 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
O2 C10 H10A 109.5 . . ?
O2 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O2 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

_refine_diff_density_max         0.691
_refine_diff_density_min         -0.528
_refine_diff_density_rms         0.061



