# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 2024

####################################################################### 
# 
# 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_vk_a
_database_code_depnum_ccdc_archive 'CCDC 2351952'
_audit_update_record             
;
2024-06-16 deposited with the CCDC.	2024-06-21 downloaded from the CCDC.
;
_audit_creation_date             2023-04-11
_audit_creation_method           
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H8 Br N O3'
_chemical_formula_sum            'C14 H8 Br N O3'
_chemical_formula_weight         318.12
_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           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                   4.7750(2)
_cell_length_b                   11.0709(5)
_cell_length_c                   22.9812(9)
_cell_angle_alpha                90
_cell_angle_beta                 95.6540(10)
_cell_angle_gamma                90
_cell_volume                     1208.96(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9985
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      25.14
_cell_measurement_theta_min      2.56
_shelx_estimated_absorpt_T_max   0.549
_shelx_estimated_absorpt_T_min   0.172
_exptl_absorpt_coefficient_mu    3.402
_exptl_absorpt_correction_T_max  0.506
_exptl_absorpt_correction_T_min  0.213
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.748
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       rhombohedral
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0699
_diffrn_reflns_av_unetI/netI     0.0273
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            37158
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.724
_diffrn_reflns_theta_min         1.781
_diffrn_ambient_temperature      273.15
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 5.6
_diffrn_detector_type            'Bruker SMART CCD 6000 area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_target            Mo
_diffrn_source_voltage           50.0
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1884
_reflns_number_total             2299
_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       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.284
_refine_diff_density_min         -0.423
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2299
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0487
_refine_ls_R_factor_gt           0.0348
_refine_ls_restrained_S_all      1.110
_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)+(0.0153P)²+1.3868P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0636
_refine_ls_wR_factor_ref         0.0687
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C11(H11), C2(H2A), C3(H3), C6(H6), C1(H1), C14(H14)
2.b Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 -0.36152(7) 0.52924(3) 0.40563(2) 0.04699(12) Uani 1 1 d . . . . .
O1 O 0.3974(4) 0.25067(19) 0.31391(9) 0.0374(5) Uani 1 1 d . . . . .
O2 O 0.3083(5) 0.0829(2) 0.47562(10) 0.0495(6) Uani 1 1 d . . . . .
H2 H 0.406403 0.062680 0.449925 0.074 Uiso 1 1 calc R U . . .
N1 N 0.5379(5) 0.0966(2) 0.37360(11) 0.0368(6) Uani 1 1 d . . . . .
O3 O -0.1962(6) 0.2113(2) 0.58929(11) 0.0678(8) Uani 1 1 d . . . . .
C7 C 0.3803(6) 0.1915(3) 0.36543(12) 0.0336(7) Uani 1 1 d . . . . .
C9 C 0.0319(6) 0.3434(3) 0.39004(13) 0.0339(7) Uani 1 1 d . . . . .
H9 H 0.047940 0.381319 0.354414 0.041 Uiso 1 1 calc R U . . .
C8 C 0.1897(6) 0.2403(3) 0.40503(12) 0.0331(7) Uani 1 1 d . . . . .
C13 C 0.1651(6) 0.1835(3) 0.45907(13) 0.0346(7) Uani 1 1 d . . . . .
C5 C 0.6779(6) 0.0888(3) 0.32277(13) 0.0350(7) Uani 1 1 d . . . . .
C4 C 0.5900(6) 0.1833(3) 0.28631(13) 0.0359(7) Uani 1 1 d . . . . .
C10 C -0.1474(6) 0.3891(3) 0.42775(13) 0.0356(7) Uani 1 1 d . . . . .
C11 C -0.1716(6) 0.3350(3) 0.48125(13) 0.0381(7) Uani 1 1 d . . . . .
H11 H -0.291998 0.367410 0.506603 0.046 Uiso 1 1 calc R U . . .
C12 C -0.0161(7) 0.2323(3) 0.49706(13) 0.0371(7) Uani 1 1 d . . . . .
C2 C 0.8837(7) 0.1235(3) 0.21680(14) 0.0474(9) Uani 1 1 d . . . . .
H2A H 0.957252 0.133607 0.181130 0.057 Uiso 1 1 calc R U . . .
C3 C 0.6842(7) 0.2045(3) 0.23267(14) 0.0425(8) Uani 1 1 d . . . . .
H3 H 0.618996 0.268524 0.208849 0.051 Uiso 1 1 calc R U . . .
C6 C 0.8769(7) 0.0073(3) 0.30593(14) 0.0435(8) Uani 1 1 d . . . . .
H6 H 0.939065 -0.057442 0.329526 0.052 Uiso 1 1 calc R U . . .
C1 C 0.9774(7) 0.0276(3) 0.25236(14) 0.0473(8) Uani 1 1 d . . . . .
H1 H 1.111667 -0.024627 0.239816 0.057 Uiso 1 1 calc R U . . .
C14 C -0.0389(8) 0.1770(3) 0.55495(15) 0.0514(9) Uani 1 1 d . . . . .
H14 H 0.076106 0.111199 0.565551 0.062 Uiso 1 1 calc R U . . .


_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 C10 1.899(3) . ?
O1 C7 1.363(3) . ?
O1 C4 1.385(3) . ?
O2 H2 0.8200 . ?
O2 C13 1.343(4) . ?
N1 C7 1.295(4) . ?
N1 C5 1.404(4) . ?
O3 C14 1.203(4) . ?
C7 C8 1.453(4) . ?
C9 H9 0.9300 . ?
C9 C8 1.391(4) . ?
C9 C10 1.374(4) . ?
C8 C13 1.407(4) . ?
C13 C12 1.397(4) . ?
C5 C4 1.380(4) . ?
C5 C6 1.392(4) . ?
C4 C3 1.374(4) . ?
C10 C11 1.383(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.386(4) . ?
C12 C14 1.478(4) . ?
C2 H2A 0.9300 . ?
C2 C3 1.383(5) . ?
C2 C1 1.387(5) . ?
C3 H3 0.9300 . ?
C6 H6 0.9300 . ?
C6 C1 1.383(5) . ?
C1 H1 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
C7 O1 C4 103.8(2) . . ?
C13 O2 H2 109.5 . . ?
C7 N1 C5 104.3(3) . . ?
O1 C7 C8 117.4(3) . . ?
N1 C7 O1 115.6(3) . . ?
N1 C7 C8 127.0(3) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C10 C9 C8 120.1(3) . . ?
C9 C8 C7 120.5(3) . . ?
C9 C8 C13 119.7(3) . . ?
C13 C8 C7 119.9(3) . . ?
O2 C13 C8 122.4(3) . . ?
O2 C13 C12 118.3(3) . . ?
C12 C13 C8 119.3(3) . . ?
C4 C5 N1 108.5(3) . . ?
C4 C5 C6 119.8(3) . . ?
C6 C5 N1 131.7(3) . . ?
C5 C4 O1 107.8(2) . . ?
C3 C4 O1 127.6(3) . . ?
C3 C4 C5 124.6(3) . . ?
C9 C10 Br1 119.0(2) . . ?
C9 C10 C11 120.8(3) . . ?
C11 C10 Br1 120.1(2) . . ?
C10 C11 H11 120.0 . . ?
C10 C11 C12 119.9(3) . . ?
C12 C11 H11 120.0 . . ?
C13 C12 C14 120.5(3) . . ?
C11 C12 C13 120.1(3) . . ?
C11 C12 C14 119.4(3) . . ?
C3 C2 H2A 118.9 . . ?
C3 C2 C1 122.1(3) . . ?
C1 C2 H2A 118.9 . . ?
C4 C3 C2 114.9(3) . . ?
C4 C3 H3 122.6 . . ?
C2 C3 H3 122.6 . . ?
C5 C6 H6 121.7 . . ?
C1 C6 C5 116.7(3) . . ?
C1 C6 H6 121.7 . . ?
C2 C1 H1 119.0 . . ?
C6 C1 C2 121.9(3) . . ?
C6 C1 H1 119.0 . . ?
O3 C14 C12 124.4(3) . . ?
O3 C14 H14 117.8 . . ?
C12 C14 H14 117.8 . . ?

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 C10 C11 C12 179.6(2) . . . . ?
O1 C7 C8 C9 0.2(4) . . . . ?
O1 C7 C8 C13 -179.5(3) . . . . ?
O1 C4 C3 C2 178.3(3) . . . . ?
O2 C13 C12 C11 -178.9(3) . . . . ?
O2 C13 C12 C14 2.6(5) . . . . ?
N1 C7 C8 C9 -179.7(3) . . . . ?
N1 C7 C8 C13 0.6(5) . . . . ?
N1 C5 C4 O1 0.3(3) . . . . ?
N1 C5 C4 C3 179.7(3) . . . . ?
N1 C5 C6 C1 -178.7(3) . . . . ?
C7 O1 C4 C5 -0.4(3) . . . . ?
C7 O1 C4 C3 -179.7(3) . . . . ?
C7 N1 C5 C4 -0.1(3) . . . . ?
C7 N1 C5 C6 179.1(3) . . . . ?
C7 C8 C13 O2 -1.4(5) . . . . ?
C7 C8 C13 C12 179.2(3) . . . . ?
C9 C8 C13 O2 178.9(3) . . . . ?
C9 C8 C13 C12 -0.5(4) . . . . ?
C9 C10 C11 C12 -0.8(5) . . . . ?
C8 C9 C10 Br1 -179.6(2) . . . . ?
C8 C9 C10 C11 0.9(5) . . . . ?
C8 C13 C12 C11 0.6(5) . . . . ?
C8 C13 C12 C14 -177.9(3) . . . . ?
C13 C12 C14 O3 -177.6(4) . . . . ?
C5 N1 C7 O1 -0.2(3) . . . . ?
C5 N1 C7 C8 179.8(3) . . . . ?
C5 C4 C3 C2 -0.9(5) . . . . ?
C5 C6 C1 C2 -0.5(5) . . . . ?
C4 O1 C7 N1 0.3(3) . . . . ?
C4 O1 C7 C8 -179.6(3) . . . . ?
C4 C5 C6 C1 0.4(5) . . . . ?
C10 C9 C8 C7 -179.9(3) . . . . ?
C10 C9 C8 C13 -0.2(4) . . . . ?
C10 C11 C12 C13 0.1(5) . . . . ?
C10 C11 C12 C14 178.6(3) . . . . ?
C11 C12 C14 O3 3.9(6) . . . . ?
C3 C2 C1 C6 0.0(5) . . . . ?
C6 C5 C4 O1 -179.0(3) . . . . ?
C6 C5 C4 C3 0.3(5) . . . . ?
C1 C2 C3 C4 0.7(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
