# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_inn-sohan-ii-251-b_mo
_database_code_depnum_ccdc_archive 'CCDC 1974453'
loop_
_audit_author_name
_audit_author_address
'SOHAN LAL'
;Indian Institute of Technology Bombay
India
;
_audit_update_record             
;
2019-12-27 deposited with the CCDC.	2026-04-22 downloaded from the CCDC.
;
_audit_creation_date             2018-02-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H16 Br N O4'
_chemical_formula_sum            'C20 H16 Br N O4'
_chemical_formula_weight         414.25
_chemical_melting_point          573-574
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   12.1893(4)
_cell_length_b                   6.7861(3)
_cell_length_c                   20.6372(8)
_cell_angle_alpha                90
_cell_angle_beta                 93.489(4)
_cell_angle_gamma                90
_cell_volume                     1703.90(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9036
_cell_measurement_temperature    150
_cell_measurement_theta_max      30.7120
_cell_measurement_theta_min      1.9790
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.439
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73070
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.615
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.207
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0562
_diffrn_reflns_av_unetI/netI     0.0378
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            14616
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.995
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_min         2.512
_diffrn_ambient_temperature      150
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -110.00  70.00   0.50    8.00    --  -20.00   0.00 -36.00  360
  2  ω    -62.00  19.00   0.50    8.00    --  -20.00 -72.00-108.00  162
  3  ω    -60.00 -30.00   0.50    8.00    --  -20.00 -72.00  36.00   60
  4  ω   -110.00  70.00   0.50    8.00    --  -20.00   0.00-180.00  360
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0084949000
_diffrn_orient_matrix_UB_12      -0.0084490000
_diffrn_orient_matrix_UB_13      -0.0341882000
_diffrn_orient_matrix_UB_21      -0.0572499000
_diffrn_orient_matrix_UB_22      -0.0113661000
_diffrn_orient_matrix_UB_23      0.0032508000
_diffrn_orient_matrix_UB_31      -0.0069887000
_diffrn_orient_matrix_UB_32      0.1035741000
_diffrn_orient_matrix_UB_33      -0.0024278000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2636
_reflns_number_total             2997
_reflns_odcompleteness_completeness 89.63
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     31.12
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.364
_refine_diff_density_min         -0.405
_refine_diff_density_rms         0.096
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         2997
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0400
_refine_ls_R_factor_gt           0.0328
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0332P)²+1.3837P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0717
_refine_ls_wR_factor_ref         0.0756
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5), C2(H2), C6(H6), C3(H3), C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C8(H8), C18(H18), C20(H20), C17(H17), C7(H7), C19(H19)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.04739(2) 0.61045(4) 0.59751(2) 0.02324(11) Uani 1 1 d . . . . .
O2 O 0.01623(15) 0.1089(3) 0.58130(9) 0.0228(4) Uani 1 1 d . . . . .
O4 O 0.38294(14) 0.0285(3) 0.55518(9) 0.0235(4) Uani 1 1 d . . . . .
O3 O -0.07254(14) 0.2338(3) 0.66632(9) 0.0230(4) Uani 1 1 d . . . . .
O1 O 0.36151(16) -0.0543(3) 0.72047(9) 0.0289(5) Uani 1 1 d . . . . .
N1 N 0.53400(17) 0.2213(3) 0.53734(11) 0.0205(5) Uani 1 1 d . . . . .
H1 H 0.5619 0.1503 0.5080 0.025 Uiso 1 1 calc R . . . .
C14 C 0.4405(2) 0.1751(4) 0.56655(12) 0.0184(5) Uani 1 1 d . . . . .
C13 C 0.4234(2) 0.3336(4) 0.61582(12) 0.0178(5) Uani 1 1 d . . . . .
C1 C 0.3268(2) 0.0844(4) 0.68825(13) 0.0201(6) Uani 1 1 d . . . . .
C5 C 0.2176(2) 0.0893(4) 0.64822(12) 0.0175(5) Uani 1 1 d . . . . .
H5 H 0.2144 -0.0150 0.6153 0.021 Uiso 1 1 calc R . . . .
C9 C 0.1059(2) 0.3835(3) 0.64473(12) 0.0158(5) Uani 1 1 d . . . . .
C16 C 0.5796(2) 0.3991(4) 0.56098(13) 0.0183(6) Uani 1 1 d . . . . .
C2 C 0.3836(2) 0.2796(4) 0.68350(13) 0.0198(6) Uani 1 1 d . . . . .
H2 H 0.4202 0.3381 0.7225 0.024 Uiso 1 1 calc R . . . .
C6 C 0.1136(2) 0.0823(4) 0.68973(12) 0.0179(6) Uani 1 1 d . . . . .
H6 H 0.0898 -0.0490 0.7028 0.021 Uiso 1 1 calc R . . . .
C15 C 0.5157(2) 0.4732(4) 0.60946(12) 0.0180(5) Uani 1 1 d . . . . .
C3 C 0.3142(2) 0.4073(4) 0.63776(12) 0.0160(5) Uani 1 1 d . . . . .
H3 H 0.3077 0.5475 0.6483 0.019 Uiso 1 1 calc R . . . .
C8 C 0.1254(2) 0.4116(4) 0.71666(13) 0.0195(6) Uani 1 1 d . . . . .
H8 H 0.1330 0.5312 0.7384 0.023 Uiso 1 1 calc R . . . .
C18 C 0.6985(2) 0.6745(4) 0.57260(14) 0.0266(6) Uani 1 1 d . . . . .
H18 H 0.7606 0.7430 0.5613 0.032 Uiso 1 1 calc R . . . .
C20 C 0.5417(2) 0.6510(4) 0.63873(13) 0.0231(6) Uani 1 1 d . . . . .
H20 H 0.4985 0.7031 0.6702 0.028 Uiso 1 1 calc R . . . .
C17 C 0.6719(2) 0.4976(4) 0.54163(13) 0.0226(6) Uani 1 1 d . . . . .
H17 H 0.7140 0.4473 0.5094 0.027 Uiso 1 1 calc R . . . .
C4 C 0.21063(19) 0.2962(4) 0.61596(12) 0.0161(5) Uani 1 1 d . . . . .
H4 H 0.2021 0.2864 0.5685 0.019 Uiso 1 1 calc R . . . .
C7 C 0.1298(2) 0.2324(4) 0.74350(13) 0.0211(6) Uani 1 1 d . . . . .
H7 H 0.1410 0.2049 0.7876 0.025 Uiso 1 1 calc R . . . .
C19 C 0.6347(2) 0.7512(4) 0.61986(14) 0.0282(6) Uani 1 1 d . . . . .
H19 H 0.6541 0.8709 0.6393 0.034 Uiso 1 1 calc R . . . .
C10 C 0.0319(2) 0.1974(4) 0.64303(12) 0.0181(5) Uani 1 1 d . . . . .
C11 C -0.0977(2) 0.1321(5) 0.56038(15) 0.0308(7) Uani 1 1 d . . . . .
H11A H -0.1236 0.0233 0.5331 0.037 Uiso 1 1 calc R . . . .
H11B H -0.1105 0.2551 0.5372 0.037 Uiso 1 1 calc R . . . .
C12 C -0.1512(2) 0.1324(4) 0.62415(14) 0.0298(7) Uani 1 1 d . . . . .
H12A H -0.2209 0.2018 0.6207 0.036 Uiso 1 1 calc R . . . .
H12B H -0.1632 -0.0008 0.6392 0.036 Uiso 1 1 calc R . . . .


_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 C9 1.935(2) . ?
O2 C10 1.411(3) . ?
O2 C11 1.437(3) . ?
O4 C14 1.231(3) . ?
O3 C10 1.409(3) . ?
O3 C12 1.431(3) . ?
O1 C1 1.213(3) . ?
N1 H1 0.8600 . ?
N1 C14 1.358(3) . ?
N1 C16 1.404(3) . ?
C14 C13 1.504(3) . ?
C13 C2 1.550(3) . ?
C13 C15 1.482(3) . ?
C13 C3 1.516(3) . ?
C1 C5 1.524(4) . ?
C1 C2 1.500(4) . ?
C5 H5 0.9800 . ?
C5 C6 1.574(3) . ?
C5 C4 1.554(3) . ?
C9 C8 1.501(4) . ?
C9 C4 1.557(3) . ?
C9 C10 1.552(3) . ?
C16 C15 1.398(4) . ?
C16 C17 1.388(4) . ?
C2 H2 0.9800 . ?
C2 C3 1.503(4) . ?
C6 H6 0.9800 . ?
C6 C7 1.510(4) . ?
C6 C10 1.553(4) . ?
C15 C20 1.378(4) . ?
C3 H3 0.9800 . ?
C3 C4 1.515(3) . ?
C8 H8 0.9300 . ?
C8 C7 1.336(4) . ?
C18 H18 0.9300 . ?
C18 C17 1.389(4) . ?
C18 C19 1.385(4) . ?
C20 H20 0.9300 . ?
C20 C19 1.398(4) . ?
C17 H17 0.9300 . ?
C4 H4 0.9800 . ?
C7 H7 0.9300 . ?
C19 H19 0.9300 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.504(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?

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
C10 O2 C11 107.4(2) . . ?
C10 O3 C12 107.1(2) . . ?
C14 N1 H1 124.2 . . ?
C14 N1 C16 111.7(2) . . ?
C16 N1 H1 124.2 . . ?
O4 C14 N1 125.9(2) . . ?
O4 C14 C13 127.3(2) . . ?
N1 C14 C13 106.8(2) . . ?
C14 C13 C2 120.3(2) . . ?
C14 C13 C3 126.7(2) . . ?
C15 C13 C14 105.1(2) . . ?
C15 C13 C2 120.8(2) . . ?
C15 C13 C3 120.0(2) . . ?
C3 C13 C2 58.70(16) . . ?
O1 C1 C5 125.3(2) . . ?
O1 C1 C2 125.0(3) . . ?
C2 C1 C5 109.7(2) . . ?
C1 C5 H5 110.9 . . ?
C1 C5 C6 114.2(2) . . ?
C1 C5 C4 106.0(2) . . ?
C6 C5 H5 110.9 . . ?
C4 C5 H5 110.9 . . ?
C4 C5 C6 103.62(19) . . ?
C8 C9 Br1 115.36(17) . . ?
C8 C9 C4 110.0(2) . . ?
C8 C9 C10 100.51(19) . . ?
C4 C9 Br1 113.36(16) . . ?
C10 C9 Br1 116.11(17) . . ?
C10 C9 C4 99.82(18) . . ?
C15 C16 N1 109.4(2) . . ?
C17 C16 N1 128.6(2) . . ?
C17 C16 C15 122.0(2) . . ?
C13 C2 H2 119.5 . . ?
C1 C2 C13 116.0(2) . . ?
C1 C2 H2 119.5 . . ?
C1 C2 C3 107.8(2) . . ?
C3 C2 C13 59.53(16) . . ?
C3 C2 H2 119.5 . . ?
C5 C6 H6 116.0 . . ?
C7 C6 C5 107.8(2) . . ?
C7 C6 H6 116.0 . . ?
C7 C6 C10 99.7(2) . . ?
C10 C6 C5 98.89(19) . . ?
C10 C6 H6 116.0 . . ?
C16 C15 C13 107.0(2) . . ?
C20 C15 C13 132.6(2) . . ?
C20 C15 C16 120.3(2) . . ?
C13 C3 H3 118.1 . . ?
C2 C3 C13 61.77(16) . . ?
C2 C3 H3 118.1 . . ?
C2 C3 C4 109.0(2) . . ?
C4 C3 C13 118.5(2) . . ?
C4 C3 H3 118.1 . . ?
C9 C8 H8 126.4 . . ?
C7 C8 C9 107.1(2) . . ?
C7 C8 H8 126.4 . . ?
C17 C18 H18 119.2 . . ?
C19 C18 H18 119.2 . . ?
C19 C18 C17 121.5(2) . . ?
C15 C20 H20 120.9 . . ?
C15 C20 C19 118.2(2) . . ?
C19 C20 H20 120.9 . . ?
C16 C17 C18 117.0(2) . . ?
C16 C17 H17 121.5 . . ?
C18 C17 H17 121.5 . . ?
C5 C4 C9 101.85(18) . . ?
C5 C4 H4 111.5 . . ?
C9 C4 H4 111.5 . . ?
C3 C4 C5 107.4(2) . . ?
C3 C4 C9 112.6(2) . . ?
C3 C4 H4 111.5 . . ?
C6 C7 H7 126.0 . . ?
C8 C7 C6 108.0(2) . . ?
C8 C7 H7 126.0 . . ?
C18 C19 C20 120.9(3) . . ?
C18 C19 H19 119.6 . . ?
C20 C19 H19 119.6 . . ?
O2 C10 C9 114.41(19) . . ?
O2 C10 C6 113.1(2) . . ?
O3 C10 O2 107.9(2) . . ?
O3 C10 C9 112.68(19) . . ?
O3 C10 C6 115.8(2) . . ?
C9 C10 C6 92.58(19) . . ?
O2 C11 H11A 111.5 . . ?
O2 C11 H11B 111.5 . . ?
O2 C11 C12 101.5(2) . . ?
H11A C11 H11B 109.3 . . ?
C12 C11 H11A 111.5 . . ?
C12 C11 H11B 111.5 . . ?
O3 C12 C11 102.8(2) . . ?
O3 C12 H12A 111.2 . . ?
O3 C12 H12B 111.2 . . ?
C11 C12 H12A 111.2 . . ?
C11 C12 H12B 111.2 . . ?
H12A C12 H12B 109.1 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.741
_oxdiff_exptl_absorpt_empirical_full_min 0.636
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Acetone'
