# 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. 
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data_lm250225
_database_code_depnum_ccdc_archive 'CCDC 2454358'
_audit_update_record             
;
2025-05-29 deposited with the CCDC.	2025-10-17 downloaded from the CCDC.
;
_audit_creation_date             2025-02-25
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H9 Br N2 O2'
_chemical_formula_sum            'C17 H9 Br N2 O2'
_chemical_formula_weight         353.17
_chemical_melting_point          ?
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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   18.9318(14)
_cell_length_b                   11.3071(6)
_cell_length_c                   15.6112(10)
_cell_angle_alpha                90
_cell_angle_beta                 121.523(7)
_cell_angle_gamma                90
_cell_volume                     2848.6(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4033
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      28.3850
_cell_measurement_theta_min      2.1960
_shelx_estimated_absorpt_T_max   0.723
_shelx_estimated_absorpt_T_min   0.671
_exptl_absorpt_coefficient_mu    2.894
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.02647
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.647
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1408
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0411
_diffrn_reflns_av_unetI/netI     0.0477
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.874
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            10889
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.874
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.680
_diffrn_reflns_theta_min         2.199
_diffrn_ambient_temperature      298(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.874
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -51.00  -9.00   0.50   21.51    --   24.18 -19.00-120.00   84
  2  ω    -51.00   5.00   0.50   21.51    --   24.18 -19.00-180.00  112
  3  ω    -72.00 -13.00   0.50   21.51    --   24.18 -19.00 -60.00  118
  4  ω    -71.00   5.00   0.50   21.51    --   24.18 -19.00  90.00  152
  5  ω    -88.00 -63.00   0.50   21.51    --  -23.24-144.00  29.00   50
  6  ω     37.00  95.00   0.50   21.51    --   24.18-144.00  29.00  116
  7  ω     41.00  99.00   0.50   21.51    --   24.18-178.00-180.00  116
  8  ω    -90.00 -32.00   0.50   21.51    --  -23.24 144.00  83.00  116
  9  ω     50.00  75.00   0.50   21.51    --   24.18 178.00  90.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0171792000
_diffrn_orient_matrix_UB_12      0.0350013000
_diffrn_orient_matrix_UB_13      -0.0362460000
_diffrn_orient_matrix_UB_21      0.0081617000
_diffrn_orient_matrix_UB_22      0.0519051000
_diffrn_orient_matrix_UB_23      0.0246368000
_diffrn_orient_matrix_UB_31      0.0443236000
_diffrn_orient_matrix_UB_32      0.0040040000
_diffrn_orient_matrix_UB_33      -0.0026782000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_target            Mo
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2580
_reflns_number_total             3529
_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 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.380
_refine_diff_density_min         -0.628
_refine_diff_density_rms         0.104
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3529
_refine_ls_number_restraints     19
_refine_ls_R_factor_all          0.0803
_refine_ls_R_factor_gt           0.0522
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0565P)²+4.1567P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1120
_refine_ls_wR_factor_ref         0.1200
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 O1A-C10 \\sim O1-C10
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C10 \\sim O1 \\sim O1A: within 2A with sigma of 0.01 and sigma for terminal
atoms of 0.02 within 2A
4. Others
 Sof(O1A)=1-FVAR(1)
 Sof(O1)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C7(H7), C4(H4), C15(H15), C12(H12), C5(H5), C13(H13), C6(H6), C14(H14)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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 0.90708(2) 0.77012(3) 0.79530(3) 0.05183(15) Uani 1 1 d . . . . .
O2 O 0.72104(16) 0.2491(2) 0.57967(19) 0.0490(6) Uani 1 1 d . . . . .
N2 N 0.64708(16) 0.4220(2) 0.5183(2) 0.0385(6) Uani 1 1 d . . . . .
O1 O 0.5398(8) 0.5560(7) 0.438(2) 0.054(3) Uani 0.77(10) 1 d D U P A 1
N1 N 0.72028(18) 0.5245(3) 0.6691(2) 0.0460(7) Uani 1 1 d . . . . .
C3 C 0.82014(18) 0.6396(3) 0.6094(2) 0.0339(7) Uani 1 1 d . . . . .
C8 C 0.75782(19) 0.5581(3) 0.5446(2) 0.0339(7) Uani 1 1 d . . . . .
C17 C 0.65763(19) 0.2991(3) 0.5234(2) 0.0352(7) Uani 1 1 d . . . . .
C16 C 0.5755(2) 0.2506(3) 0.4457(2) 0.0373(7) Uani 1 1 d . . . . .
C2 C 0.82849(19) 0.6599(3) 0.7035(2) 0.0378(7) Uani 1 1 d . . . . .
C9 C 0.71127(19) 0.5043(3) 0.5818(2) 0.0363(7) Uani 1 1 d . . . . .
C11 C 0.52131(19) 0.3440(3) 0.4005(2) 0.0385(7) Uani 1 1 d . . . . .
C1 C 0.7792(2) 0.6038(3) 0.7301(3) 0.0451(8) Uani 1 1 d . . . . .
H1 H 0.786029 0.620518 0.792344 0.054 Uiso 1 1 calc R U . . .
C7 C 0.7441(2) 0.5377(3) 0.4475(2) 0.0427(8) Uani 1 1 d . . . . .
H7 H 0.703957 0.483787 0.404642 0.051 Uiso 1 1 calc R U . . .
C4 C 0.8673(2) 0.6973(3) 0.5754(3) 0.0436(8) Uani 1 1 d . . . . .
H4 H 0.909119 0.749637 0.617642 0.052 Uiso 1 1 calc R U . . .
C10 C 0.5651(2) 0.4560(3) 0.4474(3) 0.0424(8) Uani 1 1 d D U . . .
C15 C 0.5514(2) 0.1353(3) 0.4179(3) 0.0526(9) Uani 1 1 d . . . . .
H15 H 0.587998 0.072793 0.449250 0.063 Uiso 1 1 calc R U . . .
C12 C 0.4406(2) 0.3247(4) 0.3239(3) 0.0518(9) Uani 1 1 d . . . . .
H12 H 0.403935 0.387233 0.293060 0.062 Uiso 1 1 calc R U . . .
C5 C 0.8517(2) 0.6765(3) 0.4809(3) 0.0515(9) Uani 1 1 d . . . . .
H5 H 0.882655 0.715421 0.458943 0.062 Uiso 1 1 calc R U . . .
C13 C 0.4162(2) 0.2098(4) 0.2947(3) 0.0593(11) Uani 1 1 d . . . . .
H13 H 0.362348 0.194514 0.242496 0.071 Uiso 1 1 calc R U . . .
C6 C 0.7898(3) 0.5972(3) 0.4169(3) 0.0506(9) Uani 1 1 d . . . . .
H6 H 0.779534 0.584897 0.352436 0.061 Uiso 1 1 calc R U . . .
C14 C 0.4702(3) 0.1164(4) 0.3414(3) 0.0636(11) Uani 1 1 d . . . . .
H14 H 0.451620 0.039447 0.320928 0.076 Uiso 1 1 calc R U . . .
O1A O 0.546(2) 0.553(3) 0.411(5) 0.046(8) Uani 0.23(10) 1 d 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
Br1 C2 1.895(3) . ?
O2 C17 1.196(4) . ?
N2 C17 1.401(4) . ?
N2 C9 1.437(4) . ?
N2 C10 1.409(4) . ?
O1 C10 1.205(7) . ?
N1 C9 1.303(4) . ?
N1 C1 1.358(4) . ?
C3 C8 1.420(4) . ?
C3 C2 1.412(4) . ?
C3 C4 1.414(5) . ?
C8 C9 1.421(4) . ?
C8 C7 1.416(5) . ?
C17 C16 1.489(4) . ?
C16 C11 1.381(5) . ?
C16 C15 1.375(5) . ?
C2 C1 1.361(5) . ?
C11 C10 1.481(5) . ?
C11 C12 1.379(5) . ?
C1 H1 0.9300 . ?
C7 H7 0.9300 . ?
C7 C6 1.365(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.366(5) . ?
C10 O1A 1.201(15) . ?
C15 H15 0.9300 . ?
C15 C14 1.384(5) . ?
C12 H12 0.9300 . ?
C12 C13 1.374(6) . ?
C5 H5 0.9300 . ?
C5 C6 1.397(5) . ?
C13 H13 0.9300 . ?
C13 C14 1.382(6) . ?
C6 H6 0.9300 . ?
C14 H14 0.9300 . ?

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
C17 N2 C9 124.0(3) . . ?
C17 N2 C10 112.4(3) . . ?
C10 N2 C9 123.5(3) . . ?
C9 N1 C1 117.3(3) . . ?
C2 C3 C8 116.5(3) . . ?
C2 C3 C4 124.4(3) . . ?
C4 C3 C8 119.0(3) . . ?
C3 C8 C9 116.7(3) . . ?
C7 C8 C3 119.2(3) . . ?
C7 C8 C9 124.2(3) . . ?
O2 C17 N2 124.7(3) . . ?
O2 C17 C16 130.1(3) . . ?
N2 C17 C16 105.2(3) . . ?
C11 C16 C17 108.4(3) . . ?
C15 C16 C17 129.7(3) . . ?
C15 C16 C11 121.9(3) . . ?
C3 C2 Br1 120.7(2) . . ?
C1 C2 Br1 117.9(2) . . ?
C1 C2 C3 121.4(3) . . ?
N1 C9 N2 115.8(3) . . ?
N1 C9 C8 125.7(3) . . ?
C8 C9 N2 118.5(3) . . ?
C16 C11 C10 109.1(3) . . ?
C12 C11 C16 120.8(3) . . ?
C12 C11 C10 130.1(3) . . ?
N1 C1 C2 122.5(3) . . ?
N1 C1 H1 118.8 . . ?
C2 C1 H1 118.8 . . ?
C8 C7 H7 120.0 . . ?
C6 C7 C8 119.9(3) . . ?
C6 C7 H7 120.0 . . ?
C3 C4 H4 119.9 . . ?
C5 C4 C3 120.2(3) . . ?
C5 C4 H4 119.9 . . ?
N2 C10 C11 104.9(3) . . ?
O1 C10 N2 123.8(6) . . ?
O1 C10 C11 131.1(6) . . ?
O1A C10 N2 123.9(18) . . ?
O1A C10 C11 127(2) . . ?
C16 C15 H15 121.5 . . ?
C16 C15 C14 117.1(4) . . ?
C14 C15 H15 121.5 . . ?
C11 C12 H12 121.1 . . ?
C13 C12 C11 117.7(4) . . ?
C13 C12 H12 121.1 . . ?
C4 C5 H5 119.6 . . ?
C4 C5 C6 120.7(3) . . ?
C6 C5 H5 119.6 . . ?
C12 C13 H13 119.3 . . ?
C12 C13 C14 121.3(3) . . ?
C14 C13 H13 119.3 . . ?
C7 C6 C5 120.9(3) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C15 C14 H14 119.4 . . ?
C13 C14 C15 121.2(4) . . ?
C13 C14 H14 119.4 . . ?

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
Br1 C2 C1 N1 179.2(3) . . . . ?
O2 C17 C16 C11 179.4(4) . . . . ?
O2 C17 C16 C15 -0.5(6) . . . . ?
N2 C17 C16 C11 -0.9(4) . . . . ?
N2 C17 C16 C15 179.1(4) . . . . ?
C3 C8 C9 N2 179.5(3) . . . . ?
C3 C8 C9 N1 0.9(5) . . . . ?
C3 C8 C7 C6 -0.8(5) . . . . ?
C3 C2 C1 N1 1.0(5) . . . . ?
C3 C4 C5 C6 -0.7(5) . . . . ?
C8 C3 C2 Br1 -178.1(2) . . . . ?
C8 C3 C2 C1 0.1(5) . . . . ?
C8 C3 C4 C5 1.3(5) . . . . ?
C8 C7 C6 C5 1.6(5) . . . . ?
C17 N2 C9 N1 -84.9(4) . . . . ?
C17 N2 C9 C8 96.3(4) . . . . ?
C17 N2 C10 O1 172(2) . . . . ?
C17 N2 C10 C11 -2.8(4) . . . . ?
C17 N2 C10 O1A -160(5) . . . . ?
C17 C16 C11 C10 -0.8(4) . . . . ?
C17 C16 C11 C12 178.8(3) . . . . ?
C17 C16 C15 C14 -179.2(4) . . . . ?
C16 C11 C10 N2 2.1(4) . . . . ?
C16 C11 C10 O1 -172(2) . . . . ?
C16 C11 C10 O1A 158(5) . . . . ?
C16 C11 C12 C13 0.3(5) . . . . ?
C16 C15 C14 C13 0.4(6) . . . . ?
C2 C3 C8 C9 -0.9(4) . . . . ?
C2 C3 C8 C7 177.4(3) . . . . ?
C2 C3 C4 C5 -176.5(3) . . . . ?
C9 N2 C17 O2 -1.1(5) . . . . ?
C9 N2 C17 C16 179.2(3) . . . . ?
C9 N2 C10 O1 -5(2) . . . . ?
C9 N2 C10 C11 -179.7(3) . . . . ?
C9 N2 C10 O1A 23(6) . . . . ?
C9 N1 C1 C2 -1.0(5) . . . . ?
C9 C8 C7 C6 177.3(3) . . . . ?
C11 C16 C15 C14 0.8(6) . . . . ?
C11 C12 C13 C14 1.0(6) . . . . ?
C1 N1 C9 N2 -178.5(3) . . . . ?
C1 N1 C9 C8 0.1(5) . . . . ?
C7 C8 C9 N2 1.3(5) . . . . ?
C7 C8 C9 N1 -177.3(3) . . . . ?
C4 C3 C8 C9 -178.9(3) . . . . ?
C4 C3 C8 C7 -0.6(4) . . . . ?
C4 C3 C2 Br1 -0.3(4) . . . . ?
C4 C3 C2 C1 177.9(3) . . . . ?
C4 C5 C6 C7 -0.8(6) . . . . ?
C10 N2 C17 O2 -178.0(3) . . . . ?
C10 N2 C17 C16 2.3(4) . . . . ?
C10 N2 C9 N1 91.6(4) . . . . ?
C10 N2 C9 C8 -87.1(4) . . . . ?
C10 C11 C12 C13 179.7(3) . . . . ?
C15 C16 C11 C10 179.2(3) . . . . ?
C15 C16 C11 C12 -1.2(5) . . . . ?
C12 C11 C10 N2 -177.4(3) . . . . ?
C12 C11 C10 O1 8(2) . . . . ?
C12 C11 C10 O1A -21(5) . . . . ?
C12 C13 C14 C15 -1.3(6) . . . . ?

_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
;
_oxdiff_exptl_absorpt_empirical_full_max 16.924
_oxdiff_exptl_absorpt_empirical_full_min 0.469
