# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_KB23_0m
_database_code_depnum_ccdc_archive 'CCDC 2101384'
loop_
_audit_author_name
_audit_author_address
'Jagadeesh Babu Nanubolu'
;CSIR Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2021-08-04 deposited with the CCDC.	2021-11-22 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         'C25 H24 Br N O5'
_chemical_formula_sum            'C25 H24 Br N O5'
_chemical_formula_weight         498.36

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                   12.333(5)
_cell_length_b                   13.046(5)
_cell_length_c                   15.250(5)
_cell_angle_alpha                90
_cell_angle_beta                 106.607(8)
_cell_angle_gamma                90
_cell_volume                     2351.2(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9985
_cell_measurement_theta_min      2.327
_cell_measurement_theta_max      27.906

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_F_000             1024
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.170
_exptl_absorpt_coefficient_mu    1.784
_shelx_estimated_absorpt_T_min   0.664
_shelx_estimated_absorpt_T_max   0.751
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6352
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   microfocus
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            37041
_diffrn_reflns_av_unetI/netI     0.0395
_diffrn_reflns_av_R_equivalents  0.0623
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.093
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5393
_reflns_number_gt                4024
_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       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_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)+(0.0421P)²+0.4928P] 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         5393
_refine_ls_number_parameters     304
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0354
_refine_ls_wR_factor_ref         0.0939
_refine_ls_wR_factor_gt          0.0870
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_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
C1 C 0.53399(18) 0.37541(15) 0.45146(14) 0.0451(5) Uani 1 1 d . . . . .
C2 C 0.62506(19) 0.38183(16) 0.53722(14) 0.0505(5) Uani 1 1 d . . . . .
H2 H 0.614945 0.351509 0.589516 0.061 Uiso 1 1 calc R U . . .
C3 C 0.72088(19) 0.42926(16) 0.54254(13) 0.0485(5) Uani 1 1 d . . . . .
H3 H 0.776876 0.427157 0.598289 0.058 Uiso 1 1 calc R U . . .
C4 C 0.74700(16) 0.48709(14) 0.46471(12) 0.0372(4) Uani 1 1 d . . . . .
C5 C 0.81852(19) 0.58015(17) 0.50417(14) 0.0552(5) Uani 1 1 d . . . . .
H5A H 0.839921 0.615146 0.456277 0.083 Uiso 1 1 calc R U . . .
H5B H 0.885260 0.558430 0.550298 0.083 Uiso 1 1 calc R U . . .
H5C H 0.775562 0.625636 0.530842 0.083 Uiso 1 1 calc R U . . .
C6 C 0.63773(14) 0.51558(12) 0.39087(11) 0.0313(3) Uani 1 1 d . . . . .
H6 H 0.601555 0.571670 0.414784 0.038 Uiso 1 1 calc R U . . .
C7 C 0.55465(17) 0.42574(15) 0.36897(13) 0.0420(4) Uani 1 1 d . . . . .
H7A H 0.482945 0.450099 0.329520 0.050 Uiso 1 1 calc R U . . .
H7B H 0.583366 0.374613 0.335145 0.050 Uiso 1 1 calc R U . . .
C8 C 0.66594(14) 0.55545(11) 0.30342(11) 0.0292(3) Uani 1 1 d . . . . .
H8 H 0.710435 0.618521 0.319134 0.035 Uiso 1 1 calc R U . . .
C9 C 0.73743(15) 0.47534(13) 0.27092(11) 0.0330(4) Uani 1 1 d . . . . .
H9 H 0.691343 0.413531 0.252631 0.040 Uiso 1 1 calc R U . . .
C10 C 0.84090(17) 0.44712(15) 0.35036(13) 0.0451(5) Uani 1 1 d . . . . .
H10A H 0.883219 0.393513 0.330691 0.054 Uiso 1 1 calc R U . . .
H10B H 0.889778 0.506536 0.366905 0.054 Uiso 1 1 calc R U . . .
C11 C 0.77788(15) 0.50991(13) 0.19035(12) 0.0343(4) Uani 1 1 d . . . . .
C12 C 0.84833(18) 0.59489(15) 0.19917(14) 0.0477(5) Uani 1 1 d . . . . .
H12 H 0.864412 0.633453 0.252641 0.057 Uiso 1 1 calc R U . . .
C13 C 0.8950(2) 0.62349(16) 0.13071(16) 0.0564(6) Uani 1 1 d . . . . .
H13 H 0.943633 0.679409 0.139107 0.068 Uiso 1 1 calc R U . . .
C14 C 0.8695(2) 0.56929(18) 0.05003(16) 0.0578(6) Uani 1 1 d . . . . .
H14 H 0.901018 0.588128 0.003837 0.069 Uiso 1 1 calc R U . . .
C15 C 0.79654(18) 0.48659(16) 0.03808(13) 0.0474(5) Uani 1 1 d . . . . .
H15 H 0.778226 0.450751 -0.016922 0.057 Uiso 1 1 calc R U . . .
C16 C 0.75019(15) 0.45621(13) 0.10703(12) 0.0349(4) Uani 1 1 d . . . . .
C17 C 0.67360(15) 0.36423(13) 0.09136(12) 0.0355(4) Uani 1 1 d . . . . .
C18 C 0.4220(2) 0.3015(2) 0.0254(2) 0.0865(9) Uani 1 1 d . . . . .
H18A H 0.385785 0.365908 0.005346 0.130 Uiso 1 1 calc R U . . .
H18B H 0.449340 0.300717 0.090970 0.130 Uiso 1 1 calc R U . . .
H18C H 0.368607 0.246830 0.005018 0.130 Uiso 1 1 calc R U . . .
C19 C 0.55641(14) 0.58052(12) 0.23096(11) 0.0313(4) Uani 1 1 d . . . . .
C20 C 0.48923(14) 0.67142(12) 0.24512(11) 0.0310(3) Uani 1 1 d . . . . .
C21 C 0.53702(15) 0.75216(13) 0.30270(14) 0.0427(4) Uani 1 1 d . . . . .
H21 H 0.613548 0.750594 0.334514 0.051 Uiso 1 1 calc R U . . .
C22 C 0.47141(18) 0.83493(15) 0.31300(15) 0.0490(5) Uani 1 1 d . . . . .
H22 H 0.503683 0.889432 0.350783 0.059 Uiso 1 1 calc R U . . .
C23 C 0.35858(17) 0.83557(16) 0.26696(13) 0.0460(5) Uani 1 1 d . . . . .
C24 C 0.30785(17) 0.75630(17) 0.21000(13) 0.0497(5) Uani 1 1 d . . . . .
H24 H 0.230820 0.757563 0.179758 0.060 Uiso 1 1 calc R U . . .
C25 C 0.37416(15) 0.67562(15) 0.19922(12) 0.0403(4) Uani 1 1 d . . . . .
H25 H 0.341391 0.622249 0.160193 0.048 Uiso 1 1 calc R U . . .
H1N H 0.573(2) 0.4237(18) -0.0230(16) 0.060 Uiso 1 1 d . U . . .
N1 N 0.58878(15) 0.36985(13) 0.01333(12) 0.0484(4) Uani 1 1 d . . . . .
O1 O 0.44776(14) 0.32754(13) 0.44613(11) 0.0668(4) Uani 1 1 d . . . . .
O2 O 0.80996(12) 0.41282(10) 0.42849(9) 0.0458(3) Uani 1 1 d . . . . .
O3 O 0.68706(11) 0.29157(9) 0.14361(9) 0.0450(3) Uani 1 1 d . . . . .
O4 O 0.51386(13) 0.28816(10) -0.01177(10) 0.0575(4) Uani 1 1 d . . . . .
O5 O 0.52037(12) 0.52590(9) 0.16416(9) 0.0460(3) Uani 1 1 d . . . . .
Br1 Br 0.2762(3) 0.9555(2) 0.2795(2) 0.0707(5) Uani 0.59(2) 1 d . U P A 1
Br1D Br 0.2604(7) 0.9380(8) 0.2880(5) 0.0909(13) Uani 0.41(2) 1 d . U P A 2


_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
C1 O1 1.216(2) . ?
C1 C2 1.463(3) . ?
C1 C7 1.504(3) . ?
C2 C3 1.316(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.517(3) . ?
C3 H3 0.9300 . ?
C4 O2 1.446(2) . ?
C4 C5 1.520(3) . ?
C4 C6 1.535(2) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 C7 1.530(2) . ?
C6 C8 1.560(2) . ?
C6 H6 0.9800 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C19 1.516(2) . ?
C8 C9 1.538(2) . ?
C8 H8 0.9800 . ?
C9 C11 1.521(2) . ?
C9 C10 1.532(3) . ?
C9 H9 0.9800 . ?
C10 O2 1.423(2) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.391(3) . ?
C11 C16 1.405(2) . ?
C12 C13 1.380(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.375(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.383(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.390(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.503(2) . ?
C17 O3 1.219(2) . ?
C17 N1 1.343(2) . ?
C18 O4 1.414(3) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 O5 1.218(2) . ?
C19 C20 1.497(2) . ?
C20 C21 1.390(2) . ?
C20 C25 1.392(2) . ?
C21 C22 1.385(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.368(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.380(3) . ?
C23 Br1D 1.891(5) . ?
C23 Br1 1.905(3) . ?
C24 C25 1.371(3) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
N1 O4 1.391(2) . ?
N1 H1N 0.88(2) . ?

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
O1 C1 C2 121.51(18) . . ?
O1 C1 C7 121.50(19) . . ?
C2 C1 C7 116.91(17) . . ?
C3 C2 C1 121.91(18) . . ?
C3 C2 H2 119.0 . . ?
C1 C2 H2 119.0 . . ?
C2 C3 C4 125.01(19) . . ?
C2 C3 H3 117.5 . . ?
C4 C3 H3 117.5 . . ?
O2 C4 C3 102.88(14) . . ?
O2 C4 C5 111.84(16) . . ?
C3 C4 C5 108.46(16) . . ?
O2 C4 C6 109.68(14) . . ?
C3 C4 C6 110.87(16) . . ?
C5 C4 C6 112.68(15) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C7 C6 C4 111.56(14) . . ?
C7 C6 C8 111.58(14) . . ?
C4 C6 C8 110.14(14) . . ?
C7 C6 H6 107.8 . . ?
C4 C6 H6 107.8 . . ?
C8 C6 H6 107.8 . . ?
C1 C7 C6 114.52(16) . . ?
C1 C7 H7A 108.6 . . ?
C6 C7 H7A 108.6 . . ?
C1 C7 H7B 108.6 . . ?
C6 C7 H7B 108.6 . . ?
H7A C7 H7B 107.6 . . ?
C19 C8 C9 112.65(14) . . ?
C19 C8 C6 108.96(14) . . ?
C9 C8 C6 109.71(12) . . ?
C19 C8 H8 108.5 . . ?
C9 C8 H8 108.5 . . ?
C6 C8 H8 108.5 . . ?
C11 C9 C10 108.58(15) . . ?
C11 C9 C8 114.17(13) . . ?
C10 C9 C8 109.46(14) . . ?
C11 C9 H9 108.2 . . ?
C10 C9 H9 108.2 . . ?
C8 C9 H9 108.2 . . ?
O2 C10 C9 112.05(16) . . ?
O2 C10 H10A 109.2 . . ?
C9 C10 H10A 109.2 . . ?
O2 C10 H10B 109.2 . . ?
C9 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
C12 C11 C16 117.94(16) . . ?
C12 C11 C9 119.89(16) . . ?
C16 C11 C9 122.12(16) . . ?
C13 C12 C11 121.75(19) . . ?
C13 C12 H12 119.1 . . ?
C11 C12 H12 119.1 . . ?
C14 C13 C12 120.0(2) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C13 C14 C15 119.53(19) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C14 C15 C16 121.01(19) . . ?
C14 C15 H15 119.5 . . ?
C16 C15 H15 119.5 . . ?
C15 C16 C11 119.70(17) . . ?
C15 C16 C17 118.87(16) . . ?
C11 C16 C17 121.40(15) . . ?
O3 C17 N1 123.21(17) . . ?
O3 C17 C16 123.70(16) . . ?
N1 C17 C16 113.09(15) . . ?
O4 C18 H18A 109.5 . . ?
O4 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O4 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O5 C19 C20 119.95(15) . . ?
O5 C19 C8 121.28(15) . . ?
C20 C19 C8 118.70(14) . . ?
C21 C20 C25 118.36(16) . . ?
C21 C20 C19 122.63(15) . . ?
C25 C20 C19 119.02(15) . . ?
C22 C21 C20 120.43(17) . . ?
C22 C21 H21 119.8 . . ?
C20 C21 H21 119.8 . . ?
C23 C22 C21 119.22(18) . . ?
C23 C22 H22 120.4 . . ?
C21 C22 H22 120.4 . . ?
C22 C23 C24 122.02(17) . . ?
C22 C23 Br1D 121.6(3) . . ?
C24 C23 Br1D 116.0(3) . . ?
C22 C23 Br1 116.54(19) . . ?
C24 C23 Br1 121.33(18) . . ?
C25 C24 C23 118.16(18) . . ?
C25 C24 H24 120.9 . . ?
C23 C24 H24 120.9 . . ?
C24 C25 C20 121.80(17) . . ?
C24 C25 H25 119.1 . . ?
C20 C25 H25 119.1 . . ?
C17 N1 O4 119.34(16) . . ?
C17 N1 H1N 125.0(16) . . ?
O4 N1 H1N 115.6(16) . . ?
C10 O2 C4 114.25(13) . . ?
N1 O4 C18 109.93(16) . . ?

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
O1 C1 C2 C3 176.6(2) . . . . ?
C7 C1 C2 C3 0.0(3) . . . . ?
C1 C2 C3 C4 3.6(3) . . . . ?
C2 C3 C4 O2 -97.5(2) . . . . ?
C2 C3 C4 C5 143.9(2) . . . . ?
C2 C3 C4 C6 19.7(3) . . . . ?
O2 C4 C6 C7 68.48(18) . . . . ?
C3 C4 C6 C7 -44.46(19) . . . . ?
C5 C4 C6 C7 -166.23(16) . . . . ?
O2 C4 C6 C8 -56.01(18) . . . . ?
C3 C4 C6 C8 -168.95(14) . . . . ?
C5 C4 C6 C8 69.28(19) . . . . ?
O1 C1 C7 C6 156.22(18) . . . . ?
C2 C1 C7 C6 -27.1(2) . . . . ?
C4 C6 C7 C1 49.6(2) . . . . ?
C8 C6 C7 C1 173.23(15) . . . . ?
C7 C6 C8 C19 54.16(18) . . . . ?
C4 C6 C8 C19 178.64(13) . . . . ?
C7 C6 C8 C9 -69.59(18) . . . . ?
C4 C6 C8 C9 54.89(18) . . . . ?
C19 C8 C9 C11 63.11(19) . . . . ?
C6 C8 C9 C11 -175.33(14) . . . . ?
C19 C8 C9 C10 -174.95(14) . . . . ?
C6 C8 C9 C10 -53.39(18) . . . . ?
C11 C9 C10 O2 -179.41(14) . . . . ?
C8 C9 C10 O2 55.36(19) . . . . ?
C10 C9 C11 C12 -60.9(2) . . . . ?
C8 C9 C11 C12 61.5(2) . . . . ?
C10 C9 C11 C16 116.49(18) . . . . ?
C8 C9 C11 C16 -121.10(18) . . . . ?
C16 C11 C12 C13 -3.3(3) . . . . ?
C9 C11 C12 C13 174.20(18) . . . . ?
C11 C12 C13 C14 2.0(3) . . . . ?
C12 C13 C14 C15 0.3(3) . . . . ?
C13 C14 C15 C16 -1.2(3) . . . . ?
C14 C15 C16 C11 -0.2(3) . . . . ?
C14 C15 C16 C17 -178.55(18) . . . . ?
C12 C11 C16 C15 2.4(3) . . . . ?
C9 C11 C16 C15 -175.06(16) . . . . ?
C12 C11 C16 C17 -179.33(16) . . . . ?
C9 C11 C16 C17 3.2(3) . . . . ?
C15 C16 C17 O3 127.11(19) . . . . ?
C11 C16 C17 O3 -51.2(2) . . . . ?
C15 C16 C17 N1 -52.5(2) . . . . ?
C11 C16 C17 N1 129.20(18) . . . . ?
C9 C8 C19 O5 15.2(2) . . . . ?
C6 C8 C19 O5 -106.81(18) . . . . ?
C9 C8 C19 C20 -167.95(13) . . . . ?
C6 C8 C19 C20 70.06(17) . . . . ?
O5 C19 C20 C21 -160.95(17) . . . . ?
C8 C19 C20 C21 22.1(2) . . . . ?
O5 C19 C20 C25 19.3(2) . . . . ?
C8 C19 C20 C25 -157.65(15) . . . . ?
C25 C20 C21 C22 -0.7(3) . . . . ?
C19 C20 C21 C22 179.54(17) . . . . ?
C20 C21 C22 C23 1.0(3) . . . . ?
C21 C22 C23 C24 -0.3(3) . . . . ?
C21 C22 C23 Br1D 172.8(5) . . . . ?
C21 C22 C23 Br1 -176.64(18) . . . . ?
C22 C23 C24 C25 -0.8(3) . . . . ?
Br1D C23 C24 C25 -174.2(5) . . . . ?
Br1 C23 C24 C25 175.39(18) . . . . ?
C23 C24 C25 C20 1.1(3) . . . . ?
C21 C20 C25 C24 -0.4(3) . . . . ?
C19 C20 C25 C24 179.36(16) . . . . ?
O3 C17 N1 O4 -2.1(3) . . . . ?
C16 C17 N1 O4 177.49(15) . . . . ?
C9 C10 O2 C4 -59.4(2) . . . . ?
C3 C4 O2 C10 177.24(16) . . . . ?
C5 C4 O2 C10 -66.6(2) . . . . ?
C6 C4 O2 C10 59.2(2) . . . . ?
C17 N1 O4 C18 89.6(2) . . . . ?

_refine_diff_density_max         0.392
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.041



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane and Hexane (3:7)'
####################################################################### 
# 
# 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_KB60_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2101385'
loop_
_audit_author_name
_audit_author_address
'Jagadeesh Babu Nanubolu'
;CSIR Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2021-08-04 deposited with the CCDC.	2021-11-22 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         'C25 H24 Br N O5'
_chemical_formula_sum            'C25 H24 Br N O5'
_chemical_formula_weight         498.36

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           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   11.355(4)
_cell_length_b                   7.423(2)
_cell_length_c                   14.224(5)
_cell_angle_alpha                90
_cell_angle_beta                 107.513(7)
_cell_angle_gamma                90
_cell_volume                     1143.3(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9979
_cell_measurement_theta_min      2.739
_cell_measurement_theta_max      24.537

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.448
_exptl_crystal_F_000             512
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    1.834
_shelx_estimated_absorpt_T_min   0.688
_shelx_estimated_absorpt_T_max   0.796
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6472
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   microfocus
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            29073
_diffrn_reflns_av_unetI/netI     0.0416
_diffrn_reflns_av_R_equivalents  0.0553
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.737
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             5218
_reflns_number_gt                4106
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.858
_reflns_Friedel_fraction_max     0.990
_reflns_Friedel_fraction_full    0.989

_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       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0489P)²+0.3748P] 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   0.491(12)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         5218
_refine_ls_number_parameters     319
_refine_ls_number_restraints     39
_refine_ls_R_factor_all          0.0608
_refine_ls_R_factor_gt           0.0419
_refine_ls_wR_factor_ref         0.1058
_refine_ls_wR_factor_gt          0.0967
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.030
_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
C1 C 0.6300(4) 0.5970(9) 0.9585(4) 0.0678(15) Uani 1 1 d . . . . .
C2 C 0.6502(5) 0.4070(8) 0.9867(4) 0.0701(16) Uani 1 1 d . . . . .
H2 H 0.660618 0.374386 1.051832 0.084 Uiso 1 1 calc R U . . .
C3 C 0.6541(4) 0.2819(7) 0.9228(4) 0.0626(14) Uani 1 1 d . . . . .
H3 H 0.667545 0.163756 0.945168 0.075 Uiso 1 1 calc R U . . .
C4 C 0.6382(3) 0.3169(7) 0.8162(3) 0.0511(10) Uani 1 1 d . . . . .
C5 C 0.7660(4) 0.3423(12) 0.8019(4) 0.0799(15) Uani 1 1 d . . . . .
H5A H 0.813813 0.234484 0.821417 0.120 Uiso 1 1 calc R U . . .
H5B H 0.807636 0.441361 0.841585 0.120 Uiso 1 1 calc R U . . .
H5C H 0.756543 0.367038 0.733762 0.120 Uiso 1 1 calc R U . . .
C6 C 0.5572(4) 0.4835(5) 0.7809(3) 0.0402(9) Uani 1 1 d . . . . .
H6 H 0.562563 0.517346 0.715765 0.048 Uiso 1 1 calc R U . . .
C7 C 0.6047(4) 0.6404(7) 0.8512(3) 0.0550(11) Uani 1 1 d . . . . .
H7A H 0.680351 0.684809 0.841118 0.066 Uiso 1 1 calc R U . . .
H7B H 0.544504 0.736987 0.834212 0.066 Uiso 1 1 calc R U . . .
C8 C 0.4210(3) 0.4435(5) 0.7716(3) 0.0352(8) Uani 1 1 d . . . . .
H8 H 0.415575 0.422505 0.838162 0.042 Uiso 1 1 calc R U . . .
C9 C 0.3730(4) 0.2698(5) 0.7096(3) 0.0397(8) Uani 1 1 d . . . . .
H9 H 0.294769 0.237092 0.720921 0.048 Uiso 1 1 calc R U . . .
C10 C 0.4644(4) 0.1201(6) 0.7535(3) 0.0506(10) Uani 1 1 d . . . . .
H10A H 0.461094 0.094280 0.819529 0.061 Uiso 1 1 calc R U . . .
H10B H 0.439260 0.012084 0.714244 0.061 Uiso 1 1 calc R U . . .
C11 C 0.3459(4) 0.2975(5) 0.5987(3) 0.0447(9) Uani 1 1 d . . . . .
C12 C 0.4402(5) 0.2957(7) 0.5551(3) 0.0645(14) Uani 1 1 d . . . . .
H12 H 0.520394 0.271066 0.593977 0.077 Uiso 1 1 calc R U . . .
C13 C 0.4183(6) 0.3295(11) 0.4552(4) 0.0812(16) Uani 1 1 d . . . . .
H13 H 0.483218 0.328075 0.427992 0.097 Uiso 1 1 calc R U . . .
C14 C 0.3011(7) 0.3649(10) 0.3973(4) 0.0853(18) Uani 1 1 d . . . . .
H14 H 0.286121 0.389450 0.330622 0.102 Uiso 1 1 calc R U . . .
C15 C 0.2054(5) 0.3643(7) 0.4372(3) 0.0685(14) Uani 1 1 d . . . . .
H15 H 0.125818 0.387773 0.396879 0.082 Uiso 1 1 calc R U . . .
C16 C 0.2249(4) 0.3290(6) 0.5374(3) 0.0480(9) Uani 1 1 d . . . . .
C17 C 0.1150(4) 0.3099(6) 0.5733(3) 0.0579(12) Uani 1 1 d . . . . .
C19 C 0.3397(3) 0.6033(5) 0.7292(3) 0.0337(8) Uani 1 1 d . . . . .
C20 C 0.2349(3) 0.6508(5) 0.7673(3) 0.0339(8) Uani 1 1 d . . . . .
C21 C 0.1932(4) 0.5375(6) 0.8284(3) 0.0442(9) Uani 1 1 d . . . . .
H21 H 0.228775 0.424505 0.844788 0.053 Uiso 1 1 calc R U . . .
C22 C 0.0987(4) 0.5927(7) 0.8650(3) 0.0499(10) Uani 1 1 d . . . . .
H22 H 0.068743 0.516011 0.904218 0.060 Uiso 1 1 calc R U . . .
C23 C 0.0504(4) 0.7608(6) 0.8427(3) 0.0473(10) Uani 1 1 d . . . . .
C24 C 0.0888(4) 0.8757(6) 0.7820(3) 0.0458(10) Uani 1 1 d . . . . .
H24 H 0.053916 0.989551 0.767448 0.055 Uiso 1 1 calc R U . . .
C25 C 0.1791(3) 0.8193(6) 0.7434(3) 0.0402(8) Uani 1 1 d . . . . .
H25 H 0.203968 0.894482 0.700619 0.048 Uiso 1 1 calc R U . . .
Br1 Br -0.07034(4) 0.84274(9) 0.90106(4) 0.0801(2) Uani 1 1 d . . . . .
O1 O 0.6376(5) 0.7152(8) 1.0180(4) 0.1095(17) Uani 1 1 d . . . . .
O2 O 0.5879(3) 0.1616(4) 0.7583(2) 0.0564(8) Uani 1 1 d . . . . .
O3 O 0.0973(4) 0.1821(5) 0.6223(3) 0.0656(10) Uani 1 1 d . . . . .
O5 O 0.3605(3) 0.6959(4) 0.6649(2) 0.0495(7) Uani 1 1 d . . . . .
C18 C -0.1692(13) 0.382(2) 0.5389(9) 0.072(3) Uani 0.620(11) 1 d . U P A 1
H18A H -0.236838 0.395923 0.565723 0.107 Uiso 0.620(11) 1 calc R U P A 1
H18B H -0.191992 0.431156 0.473330 0.107 Uiso 0.620(11) 1 calc R U P A 1
H18C H -0.149715 0.256914 0.536801 0.107 Uiso 0.620(11) 1 calc R U P A 1
N1 N 0.0370(9) 0.4594(13) 0.5622(9) 0.063(2) Uani 0.620(11) 1 d . . P A 1
H1 H 0.051876 0.548892 0.529029 0.075 Uiso 0.620(11) 1 calc R U P A 1
O4 O -0.0630(7) 0.4772(11) 0.6000(5) 0.074(2) Uani 0.620(11) 1 d . U P A 1
C18D C -0.132(3) 0.379(4) 0.590(2) 0.084(7) Uani 0.380(11) 1 d . U P A 2
H18D H -0.212395 0.327561 0.582538 0.127 Uiso 0.380(11) 1 calc R U P A 2
H18E H -0.074644 0.334621 0.649339 0.127 Uiso 0.380(11) 1 calc R U P A 2
H18F H -0.137333 0.507518 0.592711 0.127 Uiso 0.380(11) 1 calc R U P A 2
N1D N 0.0219(12) 0.400(2) 0.5157(11) 0.053(3) Uani 0.380(11) 1 d . . P A 2
H1D H 0.031543 0.495018 0.484448 0.064 Uiso 0.380(11) 1 calc R U P A 2
O4D O -0.0932(7) 0.3293(16) 0.5090(6) 0.062(3) Uani 0.380(11) 1 d . U P A 2


_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
C1 O1 1.204(7) . ?
C1 C2 1.465(9) . ?
C1 C7 1.501(8) . ?
C2 C3 1.309(7) . ?
C3 C4 1.495(7) . ?
C4 O2 1.432(6) . ?
C4 C6 1.533(6) . ?
C4 C5 1.537(6) . ?
C6 C7 1.524(6) . ?
C6 C8 1.540(5) . ?
C8 C19 1.513(5) . ?
C8 C9 1.564(5) . ?
C9 C10 1.520(6) . ?
C9 C11 1.527(6) . ?
C10 O2 1.418(6) . ?
C11 C12 1.390(6) . ?
C11 C16 1.408(6) . ?
C12 C13 1.390(7) . ?
C13 C14 1.363(9) . ?
C14 C15 1.368(9) . ?
C15 C16 1.400(6) . ?
C16 C17 1.489(7) . ?
C17 O3 1.229(6) . ?
C17 N1D 1.308(14) . ?
C17 N1 1.399(10) . ?
C19 O5 1.223(4) . ?
C19 C20 1.490(5) . ?
C20 C21 1.391(5) . ?
C20 C25 1.397(6) . ?
C21 C22 1.389(6) . ?
C22 C23 1.361(7) . ?
C23 C24 1.374(6) . ?
C23 Br1 1.904(4) . ?
C24 C25 1.366(5) . ?
C18 O4 1.441(17) . ?
N1 O4 1.401(12) . ?
C18D O4D 1.40(2) . ?
N1D O4D 1.384(15) . ?

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
O1 C1 C2 122.5(6) . . ?
O1 C1 C7 120.7(6) . . ?
C2 C1 C7 116.8(5) . . ?
C3 C2 C1 121.9(5) . . ?
C2 C3 C4 124.2(5) . . ?
O2 C4 C3 110.4(4) . . ?
O2 C4 C6 111.4(3) . . ?
C3 C4 C6 110.5(4) . . ?
O2 C4 C5 104.6(4) . . ?
C3 C4 C5 109.0(4) . . ?
C6 C4 C5 110.8(5) . . ?
C7 C6 C4 110.0(3) . . ?
C7 C6 C8 110.6(3) . . ?
C4 C6 C8 111.1(3) . . ?
C1 C7 C6 115.1(4) . . ?
C19 C8 C6 111.1(3) . . ?
C19 C8 C9 110.8(3) . . ?
C6 C8 C9 112.2(3) . . ?
C10 C9 C11 115.0(3) . . ?
C10 C9 C8 107.0(3) . . ?
C11 C9 C8 113.5(3) . . ?
O2 C10 C9 113.8(4) . . ?
C12 C11 C16 117.7(4) . . ?
C12 C11 C9 121.1(4) . . ?
C16 C11 C9 121.2(4) . . ?
C11 C12 C13 122.0(5) . . ?
C14 C13 C12 119.6(5) . . ?
C13 C14 C15 120.1(5) . . ?
C14 C15 C16 121.4(5) . . ?
C15 C16 C11 119.2(4) . . ?
C15 C16 C17 118.4(4) . . ?
C11 C16 C17 122.2(4) . . ?
O3 C17 N1D 120.6(7) . . ?
O3 C17 N1 118.0(6) . . ?
O3 C17 C16 124.4(4) . . ?
N1D C17 C16 109.8(7) . . ?
N1 C17 C16 116.9(5) . . ?
O5 C19 C20 119.6(3) . . ?
O5 C19 C8 120.4(3) . . ?
C20 C19 C8 120.0(3) . . ?
C21 C20 C25 118.6(3) . . ?
C21 C20 C19 122.9(3) . . ?
C25 C20 C19 118.5(3) . . ?
C22 C21 C20 120.2(4) . . ?
C23 C22 C21 119.0(4) . . ?
C22 C23 C24 122.3(4) . . ?
C22 C23 Br1 118.9(3) . . ?
C24 C23 Br1 118.8(3) . . ?
C25 C24 C23 118.7(4) . . ?
C24 C25 C20 121.1(4) . . ?
C10 O2 C4 114.8(3) . . ?
C17 N1 O4 126.2(8) . . ?
N1 O4 C18 110.5(9) . . ?
C17 N1D O4D 114.8(10) . . ?
N1D O4D C18D 111.8(17) . . ?

_refine_diff_density_max         0.512
_refine_diff_density_min         -0.382
_refine_diff_density_rms         0.047



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane and Hexane (3:7)'
