# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry B.
# This journal is © The Royal Society of Chemistry 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_1_a
_database_code_depnum_ccdc_archive 'CCDC 2142628'
loop_
_audit_author_name
_audit_author_address
'Ranajit Das'
;Shiv Nadar University
India
;
_audit_update_record             
;
2022-01-17 deposited with the CCDC.	2023-01-29 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         'C26 H14 Br N O2'
_chemical_formula_sum            'C26 H14 Br N O2'
_chemical_formula_weight         452.28

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/c'
_space_group_name_Hall           '-P 2ybc'

_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, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.2943(4)
_cell_length_b                   9.2072(5)
_cell_length_c                   18.9546(9)
_cell_angle_alpha                90
_cell_angle_beta                 103.620(2)
_cell_angle_gamma                90
_cell_volume                     1915.64(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    3927
_cell_measurement_theta_min      2.211
_cell_measurement_theta_max      26.387

_exptl_crystal_description       Needle
_exptl_crystal_colour            Yellowish
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.568
_exptl_crystal_F_000             912
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.144
_exptl_crystal_size_mid          0.116
_exptl_crystal_size_min          0.101
_exptl_absorpt_coefficient_mu    2.170
_shelx_estimated_absorpt_T_min   0.178
_shelx_estimated_absorpt_T_max   0.268
_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      300(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   X-ray
_diffrn_measurement_device_type  'Bruker PHOTON100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31583
_diffrn_reflns_av_unetI/netI     0.0357
_diffrn_reflns_av_R_equivalents  0.0563
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.211
_diffrn_reflns_theta_max         26.387
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3912
_reflns_number_gt                3202
_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-2018/3 (Sheldrick, 2018)'
_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)] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0012(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3927
_refine_ls_number_parameters     328
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0449
_refine_ls_R_factor_gt           0.0337
_refine_ls_wR_factor_ref         0.0815
_refine_ls_wR_factor_gt          0.0785
_refine_ls_goodness_of_fit_ref   1.846
_refine_ls_restrained_S_all      1.846
_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 -0.14947(2) 0.97909(3) 0.27964(2) 0.06486(14) Uani 1 1 d . . . . .
O1 O 0.60178(15) 0.50404(16) 0.66169(11) 0.0625(5) Uani 1 1 d . . . . .
O2 O 0.14027(14) 0.71147(18) 0.58112(9) 0.0629(5) Uani 1 1 d . . . . .
N1 N 0.42804(15) 0.76549(17) 0.47191(9) 0.0418(4) Uani 1 1 d . . . . .
C24 C -0.00464(18) 0.9155(2) 0.34543(12) 0.0431(5) Uani 1 1 d . . . . .
C21 C 0.20501(17) 0.8197(2) 0.44071(11) 0.0392(5) Uani 1 1 d . . . . .
C25 C 0.0536(2) 0.7941(2) 0.32851(13) 0.0487(5) Uani 1 1 d . . . . .
C5 C 0.28587(18) 0.5734(2) 0.66418(11) 0.0421(5) Uani 1 1 d . . . . .
C6 C 0.4058(2) 0.5211(2) 0.68324(12) 0.0413(5) Uani 1 1 d . . . . .
C7 C 0.49890(18) 0.5562(2) 0.64164(12) 0.0427(5) Uani 1 1 d . . . . .
C26 C 0.1586(2) 0.7478(2) 0.37556(12) 0.0480(5) Uani 1 1 d . . . . .
C9 C 0.33486(17) 0.6954(2) 0.55680(11) 0.0390(5) Uani 1 1 d . . . . .
C12 C 0.31636(17) 0.7645(2) 0.49107(11) 0.0398(5) Uani 1 1 d . . . . .
C8 C 0.45906(17) 0.6483(2) 0.57809(11) 0.0379(4) Uani 1 1 d . . . . .
C23 C 0.0398(2) 0.9905(2) 0.40878(14) 0.0488(5) Uani 1 1 d . . . . .
C10 C 0.24433(19) 0.6651(2) 0.59819(12) 0.0440(5) Uani 1 1 d . . . . .
C11 C 0.51693(17) 0.6963(2) 0.52459(12) 0.0386(5) Uani 1 1 d . . . . .
C13 C 0.63903(18) 0.6899(2) 0.51238(12) 0.0410(5) Uani 1 1 d . . . . .
C22 C 0.1446(2) 0.9419(2) 0.45616(13) 0.0474(5) Uani 1 1 d . . . . .
C18 C 0.65916(19) 0.7491(2) 0.44730(12) 0.0456(5) Uani 1 1 d . . . . .
C4 C 0.2036(2) 0.5348(3) 0.70432(14) 0.0538(6) Uani 1 1 d . . . . .
C20 C 0.4510(2) 0.8296(3) 0.41016(13) 0.0514(6) Uani 1 1 d . . . . .
C14 C 0.7386(2) 0.6298(3) 0.56167(15) 0.0523(6) Uani 1 1 d . . . . .
C17 C 0.7750(2) 0.7382(3) 0.43308(15) 0.0544(6) Uani 1 1 d . . . . .
C16 C 0.8689(2) 0.6755(3) 0.48130(16) 0.0581(7) Uani 1 1 d . . . . .
C1 C 0.4390(2) 0.4289(2) 0.74344(14) 0.0518(6) Uani 1 1 d . . . . .
C3 C 0.2382(3) 0.4433(3) 0.76342(14) 0.0588(6) Uani 1 1 d . . . . .
C19 C 0.5610(2) 0.8214(3) 0.39755(14) 0.0550(6) Uani 1 1 d . . . . .
C15 C 0.8510(2) 0.6233(3) 0.54612(16) 0.0604(7) Uani 1 1 d . . . . .
C2 C 0.3555(2) 0.3906(3) 0.78255(14) 0.0573(6) Uani 1 1 d . . . . .
H12 H 0.0218(19) 0.748(2) 0.2857(13) 0.049(6) Uiso 1 1 d . . . . .
H10 H 0.3841(19) 0.872(2) 0.3823(12) 0.044(6) Uiso 1 1 d . . . . .
H11 H 0.201(2) 0.666(2) 0.3672(12) 0.049(6) Uiso 1 1 d . . . . .
H4 H 0.121(2) 0.575(3) 0.6869(15) 0.071(7) Uiso 1 1 d . . . . .
H1 H 0.517(2) 0.393(2) 0.7539(11) 0.044(6) Uiso 1 1 d . . . . .
H5 H 0.730(2) 0.596(2) 0.6022(13) 0.055(7) Uiso 1 1 d . . . . .
H14 H 0.173(3) 0.986(2) 0.4992(16) 0.067(8) Uiso 1 1 d . . . . .
H6 H 0.917(2) 0.583(3) 0.5812(15) 0.072(8) Uiso 1 1 d . . . . .
H13 H -0.002(2) 1.076(3) 0.4212(14) 0.069(7) Uiso 1 1 d . . . . .
H8 H 0.783(2) 0.776(2) 0.3896(14) 0.064(8) Uiso 1 1 d . . . . .
H2 H 0.375(2) 0.333(3) 0.8205(14) 0.065(8) Uiso 1 1 d . . . . .
H9 H 0.576(2) 0.865(3) 0.3561(15) 0.075(8) Uiso 1 1 d . . . . .
H7 H 0.938(2) 0.666(2) 0.4687(14) 0.065(7) Uiso 1 1 d . . . . .
H3 H 0.179(2) 0.417(3) 0.7888(15) 0.073(8) Uiso 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
Br1 C24 1.9006(19) . ?
O1 C7 1.232(2) . ?
O2 C10 1.220(2) . ?
N1 C20 1.389(3) . ?
N1 C12 1.392(3) . ?
N1 C11 1.392(2) . ?
C24 C23 1.373(3) . ?
C24 C25 1.372(3) . ?
C21 C22 1.383(3) . ?
C21 C26 1.390(3) . ?
C21 C12 1.478(3) . ?
C25 C26 1.373(3) . ?
C5 C4 1.379(3) . ?
C5 C6 1.403(3) . ?
C5 C10 1.490(3) . ?
C6 C1 1.401(3) . ?
C6 C7 1.490(3) . ?
C7 C8 1.455(3) . ?
C9 C12 1.371(3) . ?
C9 C8 1.432(3) . ?
C9 C10 1.455(3) . ?
C8 C11 1.401(3) . ?
C23 C22 1.381(3) . ?
C11 C13 1.452(3) . ?
C13 C14 1.396(3) . ?
C13 C18 1.415(3) . ?
C18 C17 1.400(3) . ?
C18 C19 1.438(3) . ?
C4 C3 1.382(4) . ?
C20 C19 1.321(3) . ?
C14 C15 1.370(3) . ?
C17 C16 1.355(4) . ?
C16 C15 1.378(4) . ?
C1 C2 1.375(3) . ?
C3 C2 1.377(4) . ?

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
C20 N1 C12 125.65(18) . . ?
C20 N1 C11 123.56(18) . . ?
C12 N1 C11 110.77(17) . . ?
C23 C24 C25 121.1(2) . . ?
C23 C24 Br1 119.97(16) . . ?
C25 C24 Br1 118.89(17) . . ?
C22 C21 C26 118.28(19) . . ?
C22 C21 C12 122.01(19) . . ?
C26 C21 C12 119.72(18) . . ?
C24 C25 C26 119.3(2) . . ?
C4 C5 C6 120.3(2) . . ?
C4 C5 C10 119.31(19) . . ?
C6 C5 C10 120.31(19) . . ?
C5 C6 C1 118.3(2) . . ?
C5 C6 C7 123.24(19) . . ?
C1 C6 C7 118.42(19) . . ?
O1 C7 C8 124.6(2) . . ?
O1 C7 C6 118.9(2) . . ?
C8 C7 C6 116.43(17) . . ?
C25 C26 C21 121.1(2) . . ?
C12 C9 C8 109.04(18) . . ?
C12 C9 C10 127.09(18) . . ?
C8 C9 C10 123.79(18) . . ?
C9 C12 N1 106.64(17) . . ?
C9 C12 C21 132.14(19) . . ?
N1 C12 C21 120.98(18) . . ?
C11 C8 C9 107.07(17) . . ?
C11 C8 C7 132.59(18) . . ?
C9 C8 C7 120.07(19) . . ?
C24 C23 C22 119.1(2) . . ?
O2 C10 C9 123.1(2) . . ?
O2 C10 C5 120.9(2) . . ?
C9 C10 C5 116.03(17) . . ?
N1 C11 C8 106.43(17) . . ?
N1 C11 C13 117.10(19) . . ?
C8 C11 C13 136.47(19) . . ?
C14 C13 C18 117.8(2) . . ?
C14 C13 C11 123.7(2) . . ?
C18 C13 C11 118.47(19) . . ?
C21 C22 C23 121.1(2) . . ?
C17 C18 C13 119.3(2) . . ?
C17 C18 C19 121.2(2) . . ?
C13 C18 C19 119.5(2) . . ?
C3 C4 C5 120.4(2) . . ?
C19 C20 N1 119.9(2) . . ?
C15 C14 C13 120.9(3) . . ?
C16 C17 C18 121.3(2) . . ?
C17 C16 C15 119.6(2) . . ?
C2 C1 C6 120.6(2) . . ?
C2 C3 C4 119.9(2) . . ?
C20 C19 C18 121.4(2) . . ?
C14 C15 C16 121.0(3) . . ?
C3 C2 C1 120.4(2) . . ?

_refine_diff_density_max         0.371
_refine_diff_density_min         -0.520
_refine_diff_density_rms         0.046



