# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2023

####################################################################### 
# 
# 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_global
_audit_block_doi                 10.5517/ccdc.csd.cc29ksl8
_database_code_depnum_ccdc_archive 'CCDC 2132260'
loop_
_audit_author_name
_audit_author_address
' Divyashree N R'
;University of Mysore
India
;
_audit_update_record             
;
2022-01-04 deposited with the CCDC.	2023-08-22 downloaded from the CCDC.
;
#============================================================================== 

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H12 Br N O2'
_chemical_formula_sum            'C13 H12 Br N O2'
_chemical_formula_weight         294.15

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'
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'

_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                   11.8284(8)
_cell_length_b                   4.5391(4)
_cell_length_c                   23.789(2)
_cell_angle_alpha                90
_cell_angle_beta                 98.165(8)
_cell_angle_gamma                90
_cell_volume                     1264.29(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2427
_cell_measurement_theta_min      2.62
_cell_measurement_theta_max      27.79

_exptl_crystal_description       rod
_exptl_crystal_colour            'dark red'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.545
_exptl_crystal_F_000             592
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.480
_exptl_crystal_size_min          0.480
_exptl_absorpt_coefficient_mu    3.240
_shelx_estimated_absorpt_T_min   0.294
_shelx_estimated_absorpt_T_max   0.305
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.14345
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd., 2009
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  
;  
Oxford Diffraction Xcalibur (TM) Single Crystal X-ray Diffractometer 
with Sapphire CCD Detector.
;
_diffrn_measurement_method       
;
Rotation method data acquisition using omega scans.
;
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4310
_diffrn_reflns_av_unetI/netI     0.0622
_diffrn_reflns_av_R_equivalents  0.0457
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.324
_diffrn_reflns_theta_max         25.347
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2312
_reflns_number_gt                1593
_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 CCD (Oxford Diffraction Ltd., 2009)
;
_computing_cell_refinement       
;
CrysAlis RED (Oxford Diffraction Ltd., 2009)
;
_computing_data_reduction        
;
CrysAlis RED (Oxford Diffraction Ltd., 2009)
;
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL-2014/6 (Sheldrick, 2014)'
_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)+(0.0945P)²] 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         2312
_refine_ls_number_parameters     158
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0981
_refine_ls_R_factor_gt           0.0686
_refine_ls_wR_factor_ref         0.1731
_refine_ls_wR_factor_gt          0.1549
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.041
_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 0.26502(5) 0.69601(16) 0.49191(3) 0.0698(3) Uani 1 1 d . . . . .
O1 O 0.8219(3) 0.0238(8) 0.38879(14) 0.0498(9) Uani 1 1 d . . . . .
O2 O 0.4207(4) 0.2382(10) 0.27820(18) 0.0630(11) Uani 1 1 d D . . . .
H2O H 0.471(4) 0.112(11) 0.281(3) 0.076 Uiso 1 1 d D U . . .
N1 N 0.5722(3) -0.0774(10) 0.34119(19) 0.0489(11) Uani 1 1 d . . . . .
C1 C 0.3863(4) 0.3356(12) 0.3269(2) 0.0474(13) Uani 1 1 d . . . . .
C2 C 0.2970(4) 0.5329(13) 0.3234(2) 0.0529(13) Uani 1 1 d . . . . .
H2 H 0.2605 0.5940 0.2881 0.064 Uiso 1 1 calc R U . . .
C3 C 0.2620(4) 0.6388(13) 0.3722(3) 0.0572(15) Uani 1 1 d . . . . .
H3 H 0.2022 0.7734 0.3697 0.069 Uiso 1 1 calc R U . . .
C4 C 0.3148(4) 0.5470(12) 0.4251(2) 0.0509(13) Uani 1 1 d . . . . .
C5 C 0.4013(4) 0.3438(11) 0.4286(2) 0.0462(13) Uani 1 1 d . . . . .
H5 H 0.4353 0.2785 0.4641 0.055 Uiso 1 1 calc R U . . .
C6 C 0.4392(4) 0.2333(10) 0.3799(2) 0.0430(12) Uani 1 1 d . . . . .
C7 C 0.5310(4) 0.0141(11) 0.3841(2) 0.0450(12) Uani 1 1 d . . . . .
H7 H 0.5599 -0.0602 0.4197 0.054 Uiso 1 1 calc R U . . .
C8 C 0.6651(5) -0.2946(12) 0.3493(3) 0.0581(15) Uani 1 1 d . . . . .
H8A H 0.6496 -0.4500 0.3213 0.070 Uiso 1 1 calc R U . . .
H8B H 0.6688 -0.3826 0.3867 0.070 Uiso 1 1 calc R U . . .
C9 C 0.7765(4) -0.1545(11) 0.3437(2) 0.0473(13) Uani 1 1 d . . . . .
C10 C 0.8466(5) -0.1630(13) 0.3047(3) 0.0606(16) Uani 1 1 d . . . . .
H10 H 0.8354 -0.2647 0.2704 0.073 Uiso 1 1 calc R U . . .
C11 C 0.9432(5) 0.0169(13) 0.3263(3) 0.0616(16) Uani 1 1 d . . . . .
H11 H 1.0069 0.0524 0.3085 0.074 Uiso 1 1 calc R U . . .
C12 C 0.9252(4) 0.1228(12) 0.3761(3) 0.0522(14) Uani 1 1 d . . . . .
C13 C 0.9902(6) 0.3196(15) 0.4192(3) 0.079(2) Uani 1 1 d . . . . .
H13A H 0.9433 0.4843 0.4263 0.119 Uiso 1 1 calc R U . . .
H13B H 1.0577 0.3893 0.4054 0.119 Uiso 1 1 calc R U . . .
H13C H 1.0115 0.2120 0.4539 0.119 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 C4 1.895(5) . ?
O1 C12 1.376(6) . ?
O1 C9 1.389(6) . ?
O2 C1 1.356(7) . ?
O2 H2O 0.82(2) . ?
N1 C7 1.263(6) . ?
N1 C8 1.469(7) . ?
C1 C2 1.379(7) . ?
C1 C6 1.403(7) . ?
C2 C3 1.373(8) . ?
C2 H2 0.9300 . ?
C3 C4 1.389(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.372(7) . ?
C5 C6 1.395(7) . ?
C5 H5 0.9300 . ?
C6 C7 1.465(7) . ?
C7 H7 0.9300 . ?
C8 C9 1.485(7) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.331(8) . ?
C10 C11 1.439(8) . ?
C10 H10 0.9300 . ?
C11 C12 1.322(7) . ?
C11 H11 0.9300 . ?
C12 C13 1.490(9) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 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
C12 O1 C9 106.2(4) . . ?
C1 O2 H2O 117(5) . . ?
C7 N1 C8 118.8(5) . . ?
O2 C1 C2 118.7(5) . . ?
O2 C1 C6 120.6(5) . . ?
C2 C1 C6 120.7(5) . . ?
C3 C2 C1 119.7(5) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C2 C3 C4 120.7(5) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C5 C4 C3 119.5(5) . . ?
C5 C4 Br1 120.5(4) . . ?
C3 C4 Br1 120.0(4) . . ?
C4 C5 C6 121.1(5) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C5 C6 C1 118.2(5) . . ?
C5 C6 C7 120.6(5) . . ?
C1 C6 C7 121.2(5) . . ?
N1 C7 C6 122.3(5) . . ?
N1 C7 H7 118.9 . . ?
C6 C7 H7 118.9 . . ?
N1 C8 C9 110.9(4) . . ?
N1 C8 H8A 109.5 . . ?
C9 C8 H8A 109.5 . . ?
N1 C8 H8B 109.5 . . ?
C9 C8 H8B 109.5 . . ?
H8A C8 H8B 108.0 . . ?
C10 C9 O1 110.1(5) . . ?
C10 C9 C8 134.3(6) . . ?
O1 C9 C8 115.6(4) . . ?
C9 C10 C11 106.1(5) . . ?
C9 C10 H10 127.0 . . ?
C11 C10 H10 127.0 . . ?
C12 C11 C10 107.8(5) . . ?
C12 C11 H11 126.1 . . ?
C10 C11 H11 126.1 . . ?
C11 C12 O1 109.8(5) . . ?
C11 C12 C13 134.6(5) . . ?
O1 C12 C13 115.6(5) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 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
O2 C1 C2 C3 -178.8(5) . . . . ?
C6 C1 C2 C3 2.4(7) . . . . ?
C1 C2 C3 C4 -0.7(8) . . . . ?
C2 C3 C4 C5 -1.3(8) . . . . ?
C2 C3 C4 Br1 -180.0(4) . . . . ?
C3 C4 C5 C6 1.7(7) . . . . ?
Br1 C4 C5 C6 -179.7(3) . . . . ?
C4 C5 C6 C1 -0.1(7) . . . . ?
C4 C5 C6 C7 -179.4(4) . . . . ?
O2 C1 C6 C5 179.2(4) . . . . ?
C2 C1 C6 C5 -2.0(7) . . . . ?
O2 C1 C6 C7 -1.4(7) . . . . ?
C2 C1 C6 C7 177.3(4) . . . . ?
C8 N1 C7 C6 179.2(4) . . . . ?
C5 C6 C7 N1 -175.6(4) . . . . ?
C1 C6 C7 N1 5.1(7) . . . . ?
C7 N1 C8 C9 -104.7(6) . . . . ?
C12 O1 C9 C10 -0.8(6) . . . . ?
C12 O1 C9 C8 178.2(4) . . . . ?
N1 C8 C9 C10 -108.1(7) . . . . ?
N1 C8 C9 O1 73.2(6) . . . . ?
O1 C9 C10 C11 0.8(6) . . . . ?
C8 C9 C10 C11 -178.0(6) . . . . ?
C9 C10 C11 C12 -0.4(7) . . . . ?
C10 C11 C12 O1 -0.1(7) . . . . ?
C10 C11 C12 C13 -179.7(7) . . . . ?
C9 O1 C12 C11 0.6(6) . . . . ?
C9 O1 C12 C13 -179.8(5) . . . . ?

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
O2 H2O N1 0.82(2) 1.93(5) 2.597(6) 137(6) .
C2 H2 O2 0.93 2.56 3.402(7) 150.8 2

_refine_diff_density_max         0.562
_refine_diff_density_min         -1.363
_refine_diff_density_rms         0.195

_shelxl_version_number           2014/6

