# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_KB854_0m
_database_code_depnum_ccdc_archive 'CCDC 2247998'
loop_
_audit_author_name
_audit_author_address
'Sridhar Balasubramanian'
;CSIR Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2023-05-18 deposited with the CCDC.	2023-07-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/2
_shelx_SHELXL_version_number     2019/2
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H16 Br N O3'
_chemical_formula_sum            'C20 H16 Br N O3'
_chemical_formula_weight         398.25

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

_cell_length_a                   9.5218(11)
_cell_length_b                   10.0470(12)
_cell_length_c                   18.931(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1811.1(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    9427
_cell_measurement_theta_min      2.9475
_cell_measurement_theta_max      28.0845

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.461
_exptl_crystal_F_000             808
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    2.287
_shelx_estimated_absorpt_T_min   0.588
_shelx_estimated_absorpt_T_max   0.684
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5305
_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
;

_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14903
_diffrn_reflns_av_unetI/netI     0.0488
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.295
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.980
_reflns_number_total             4082
_reflns_number_gt                3558
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.736
_reflns_Friedel_fraction_max     0.972
_reflns_Friedel_fraction_full    0.965

_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 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
 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)+(0.0335P)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_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.030(10)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         4082
_refine_ls_number_parameters     233
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.0338
_refine_ls_R_factor_gt           0.0280
_refine_ls_wR_factor_ref         0.0726
_refine_ls_wR_factor_gt          0.0707
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.057
_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 0.6093(2) 0.6150(2) 0.64671(12) 0.0360(5) Uani 1 1 d . . . . .
C2 C 0.7237(3) 0.5511(3) 0.67592(13) 0.0436(6) Uani 1 1 d . . . . .
H2 H 0.773760 0.590363 0.712588 0.052 Uiso 1 1 calc R U . . .
C3 C 0.7633(3) 0.4266(3) 0.64971(14) 0.0450(6) Uani 1 1 d . . . . .
H3 H 0.839481 0.381771 0.669204 0.054 Uiso 1 1 calc R U . . .
C4 C 0.6889(3) 0.3708(2) 0.59484(14) 0.0435(6) Uani 1 1 d . . . . .
C5 C 0.5753(3) 0.4329(2) 0.56364(14) 0.0442(6) Uani 1 1 d . . . . .
H5 H 0.526189 0.393385 0.526706 0.053 Uiso 1 1 calc R U . . .
C6 C 0.5378(2) 0.5559(2) 0.58964(13) 0.0385(5) Uani 1 1 d . . . . .
C7 C 0.4292(2) 0.6510(2) 0.56921(13) 0.0420(6) Uani 1 1 d . . . . .
C8 C 0.3238(3) 0.6679(3) 0.51377(16) 0.0551(7) Uani 1 1 d . . . . .
C9 C 0.3270(3) 0.8600(3) 0.58453(16) 0.0531(7) Uani 1 1 d . . . . .
C10 C 0.2090(4) 0.8903(4) 0.6358(2) 0.0861(12) Uani 1 1 d . . . . .
H10A H 0.135163 0.936500 0.611424 0.129 Uiso 1 1 calc R U . . .
H10B H 0.243938 0.945039 0.673420 0.129 Uiso 1 1 calc R U . . .
H10C H 0.173085 0.808605 0.654857 0.129 Uiso 1 1 calc R U . . .
C11 C 0.3955(4) 0.9853(3) 0.5553(2) 0.0750(10) Uani 1 1 d . . . . .
H11A H 0.473581 0.961055 0.525863 0.113 Uiso 1 1 calc R U . . .
H11B H 0.428052 1.039606 0.593649 0.113 Uiso 1 1 calc R U . . .
H11C H 0.328171 1.034136 0.527884 0.113 Uiso 1 1 calc R U . . .
C12 C 0.4312(3) 0.7583(3) 0.60958(14) 0.0408(6) Uani 1 1 d . . . . .
C13 C 0.5424(2) 0.7484(2) 0.66684(12) 0.0359(5) Uani 1 1 d . . . . .
C14 C 0.4729(3) 0.7385(3) 0.74021(13) 0.0457(6) Uani 1 1 d . . . . .
H14A H 0.419223 0.818695 0.749352 0.055 Uiso 1 1 calc R U . . .
H14B H 0.408591 0.663592 0.740862 0.055 Uiso 1 1 calc R U . . .
C15 C 0.6763(3) 0.8184(3) 0.79263(13) 0.0483(6) Uani 1 1 d . . . . .
C16 C 0.7096(2) 0.8867(3) 0.73051(14) 0.0412(6) Uani 1 1 d . . . . .
C17 C 0.8166(3) 0.9811(3) 0.73245(18) 0.0580(7) Uani 1 1 d . . . . .
H17 H 0.841380 1.027079 0.691682 0.070 Uiso 1 1 calc R U . . .
C18 C 0.8861(4) 1.0062(4) 0.7954(3) 0.0812(12) Uani 1 1 d . U . . .
H18 H 0.956841 1.070003 0.796504 0.097 Uiso 1 1 calc R U . . .
C19 C 0.8529(4) 0.9389(5) 0.8561(2) 0.0833(12) Uani 1 1 d . U . . .
H19 H 0.900761 0.956643 0.897886 0.100 Uiso 1 1 calc R U . . .
C20 C 0.7485(3) 0.8452(4) 0.85471(16) 0.0703(9) Uani 1 1 d . . . . .
H20 H 0.725664 0.799181 0.895752 0.084 Uiso 1 1 calc R U . . .
N1 N 0.6348(2) 0.8635(2) 0.66865(12) 0.0408(5) Uani 1 1 d D . . . .
H1N H 0.674(3) 0.870(3) 0.6315(12) 0.042(8) Uiso 1 1 d D . . . .
O1 O 0.2893(3) 0.5947(2) 0.46673(12) 0.0766(7) Uani 1 1 d . . . . .
O2 O 0.2640(2) 0.78818(19) 0.52351(12) 0.0648(6) Uani 1 1 d . . . . .
O3 O 0.5754(2) 0.7217(2) 0.79396(9) 0.0546(5) Uani 1 1 d . . . . .
Br1 Br 0.74276(3) 0.19931(2) 0.56153(2) 0.06015(13) Uani 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
C1 C2 1.380(3) . ?
C1 C6 1.408(3) . ?
C1 C13 1.532(3) . ?
C2 C3 1.398(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.377(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.382(4) . ?
C4 Br1 1.905(2) . ?
C5 C6 1.377(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.460(3) . ?
C7 C12 1.322(3) . ?
C7 C8 1.462(3) . ?
C8 O1 1.201(3) . ?
C8 O2 1.348(3) . ?
C9 O2 1.488(3) . ?
C9 C12 1.501(4) . ?
C9 C10 1.516(5) . ?
C9 C11 1.522(4) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.519(3) . ?
C13 N1 1.453(3) . ?
C13 C14 1.542(4) . ?
C14 O3 1.420(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 O3 1.367(3) . ?
C15 C20 1.388(4) . ?
C15 C16 1.398(4) . ?
C16 N1 1.391(3) . ?
C16 C17 1.393(4) . ?
C17 C18 1.387(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.370(6) . ?
C18 H18 0.9300 . ?
C19 C20 1.369(5) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
N1 H1N 0.80(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
C2 C1 C6 119.5(2) . . ?
C2 C1 C13 129.5(2) . . ?
C6 C1 C13 111.02(19) . . ?
C1 C2 C3 119.2(2) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 H2 120.4 . . ?
C4 C3 C2 119.6(2) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C3 C4 C5 122.8(2) . . ?
C3 C4 Br1 118.7(2) . . ?
C5 C4 Br1 118.5(2) . . ?
C6 C5 C4 117.1(2) . . ?
C6 C5 H5 121.5 . . ?
C4 C5 H5 121.5 . . ?
C5 C6 C1 121.8(2) . . ?
C5 C6 C7 132.5(2) . . ?
C1 C6 C7 105.7(2) . . ?
C12 C7 C6 111.7(2) . . ?
C12 C7 C8 109.3(2) . . ?
C6 C7 C8 138.8(2) . . ?
O1 C8 O2 122.3(2) . . ?
O1 C8 C7 130.5(3) . . ?
O2 C8 C7 107.2(2) . . ?
O2 C9 C12 100.5(2) . . ?
O2 C9 C10 107.2(3) . . ?
C12 C9 C10 115.1(3) . . ?
O2 C9 C11 106.9(2) . . ?
C12 C9 C11 113.2(3) . . ?
C10 C9 C11 112.6(3) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C7 C12 C9 111.3(2) . . ?
C7 C12 C13 111.7(2) . . ?
C9 C12 C13 137.0(2) . . ?
N1 C13 C12 112.8(2) . . ?
N1 C13 C1 116.76(19) . . ?
C12 C13 C1 99.76(19) . . ?
N1 C13 C14 106.9(2) . . ?
C12 C13 C14 110.4(2) . . ?
C1 C13 C14 110.2(2) . . ?
O3 C14 C13 111.0(2) . . ?
O3 C14 H14A 109.4 . . ?
C13 C14 H14A 109.4 . . ?
O3 C14 H14B 109.4 . . ?
C13 C14 H14B 109.4 . . ?
H14A C14 H14B 108.0 . . ?
O3 C15 C20 118.1(3) . . ?
O3 C15 C16 121.6(2) . . ?
C20 C15 C16 120.3(3) . . ?
N1 C16 C17 120.7(3) . . ?
N1 C16 C15 120.7(2) . . ?
C17 C16 C15 118.6(2) . . ?
C18 C17 C16 119.7(3) . . ?
C18 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
C19 C18 C17 121.4(3) . . ?
C19 C18 H18 119.3 . . ?
C17 C18 H18 119.3 . . ?
C20 C19 C18 119.4(3) . . ?
C20 C19 H19 120.3 . . ?
C18 C19 H19 120.3 . . ?
C19 C20 C15 120.6(3) . . ?
C19 C20 H20 119.7 . . ?
C15 C20 H20 119.7 . . ?
C16 N1 C13 117.6(2) . . ?
C16 N1 H1N 119(2) . . ?
C13 N1 H1N 109(2) . . ?
C8 O2 C9 111.7(2) . . ?
C15 O3 C14 112.7(2) . . ?

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
C6 C1 C2 C3 -2.1(3) . . . . ?
C13 C1 C2 C3 178.1(2) . . . . ?
C1 C2 C3 C4 0.8(4) . . . . ?
C2 C3 C4 C5 0.2(4) . . . . ?
C2 C3 C4 Br1 -178.66(18) . . . . ?
C3 C4 C5 C6 0.2(4) . . . . ?
Br1 C4 C5 C6 179.08(18) . . . . ?
C4 C5 C6 C1 -1.6(3) . . . . ?
C4 C5 C6 C7 177.8(3) . . . . ?
C2 C1 C6 C5 2.6(4) . . . . ?
C13 C1 C6 C5 -177.6(2) . . . . ?
C2 C1 C6 C7 -177.0(2) . . . . ?
C13 C1 C6 C7 2.8(3) . . . . ?
C5 C6 C7 C12 180.0(3) . . . . ?
C1 C6 C7 C12 -0.5(3) . . . . ?
C5 C6 C7 C8 -5.7(5) . . . . ?
C1 C6 C7 C8 173.8(3) . . . . ?
C12 C7 C8 O1 179.9(4) . . . . ?
C6 C7 C8 O1 5.5(6) . . . . ?
C12 C7 C8 O2 -0.4(3) . . . . ?
C6 C7 C8 O2 -174.8(3) . . . . ?
C6 C7 C12 C9 175.4(2) . . . . ?
C8 C7 C12 C9 -0.6(3) . . . . ?
C6 C7 C12 C13 -2.1(3) . . . . ?
C8 C7 C12 C13 -178.1(2) . . . . ?
O2 C9 C12 C7 1.2(3) . . . . ?
C10 C9 C12 C7 115.9(3) . . . . ?
C11 C9 C12 C7 -112.5(3) . . . . ?
O2 C9 C12 C13 177.9(3) . . . . ?
C10 C9 C12 C13 -67.4(4) . . . . ?
C11 C9 C12 C13 64.2(4) . . . . ?
C7 C12 C13 N1 128.1(2) . . . . ?
C9 C12 C13 N1 -48.6(4) . . . . ?
C7 C12 C13 C1 3.5(3) . . . . ?
C9 C12 C13 C1 -173.1(3) . . . . ?
C7 C12 C13 C14 -112.5(2) . . . . ?
C9 C12 C13 C14 70.9(4) . . . . ?
C2 C1 C13 N1 54.2(3) . . . . ?
C6 C1 C13 N1 -125.6(2) . . . . ?
C2 C1 C13 C12 176.0(2) . . . . ?
C6 C1 C13 C12 -3.8(2) . . . . ?
C2 C1 C13 C14 -67.9(3) . . . . ?
C6 C1 C13 C14 112.3(2) . . . . ?
N1 C13 C14 O3 -60.3(3) . . . . ?
C12 C13 C14 O3 176.8(2) . . . . ?
C1 C13 C14 O3 67.5(3) . . . . ?
O3 C15 C16 N1 3.8(4) . . . . ?
C20 C15 C16 N1 -177.9(3) . . . . ?
O3 C15 C16 C17 -178.0(2) . . . . ?
C20 C15 C16 C17 0.3(4) . . . . ?
N1 C16 C17 C18 177.5(3) . . . . ?
C15 C16 C17 C18 -0.7(4) . . . . ?
C16 C17 C18 C19 0.7(5) . . . . ?
C17 C18 C19 C20 -0.3(6) . . . . ?
C18 C19 C20 C15 -0.1(5) . . . . ?
O3 C15 C20 C19 178.5(3) . . . . ?
C16 C15 C20 C19 0.1(5) . . . . ?
C17 C16 N1 C13 169.4(2) . . . . ?
C15 C16 N1 C13 -12.5(3) . . . . ?
C12 C13 N1 C16 160.1(2) . . . . ?
C1 C13 N1 C16 -85.3(3) . . . . ?
C14 C13 N1 C16 38.6(3) . . . . ?
O1 C8 O2 C9 -179.0(3) . . . . ?
C7 C8 O2 C9 1.2(3) . . . . ?
C12 C9 O2 C8 -1.4(3) . . . . ?
C10 C9 O2 C8 -122.1(3) . . . . ?
C11 C9 O2 C8 117.0(3) . . . . ?
C20 C15 O3 C14 155.8(3) . . . . ?
C16 C15 O3 C14 -25.8(3) . . . . ?
C13 C14 O3 C15 54.3(3) . . . . ?

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
_geom_hbond_publ_flag
N1 H1N O1 0.80(2) 2.19(2) 2.985(3) 175(3) 2_566 yes

_refine_diff_density_max         0.260
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.039

