# 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_5704-br
_database_code_depnum_ccdc_archive 'CCDC 2387577'
loop_
_audit_author_name
_audit_author_address
'Huawen Huang'
;Xiangtan University
China
;
_audit_update_record             
;
2024-09-29 deposited with the CCDC.	2024-12-16 downloaded from the CCDC.
;
_audit_creation_date             2023-12-09
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H11 Br F N O2'
_chemical_formula_sum            'C10 H11 Br F N O2'
_chemical_formula_weight         276.11
_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'
F F 0.0171 0.0103 '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                   12.740(3)
_cell_length_b                   7.5412(12)
_cell_length_c                   12.056(4)
_cell_angle_alpha                90
_cell_angle_beta                 109.42(3)
_cell_angle_gamma                90
_cell_volume                     1092.4(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    976
_cell_measurement_temperature    292.99(10)
_cell_measurement_theta_max      23.0320
_cell_measurement_theta_min      3.1910
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.756
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.01567
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.679
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1039
_diffrn_reflns_av_unetI/netI     0.1315
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4036
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         3.189
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      292.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     71.00  97.00   1.00    8.00    --   12.05-178.00 120.00   26
  2  ω    -70.00  80.00   1.00    8.00    --   12.05   0.00-180.00  150
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0240087000
_diffrn_orient_matrix_UB_12      0.0559606000
_diffrn_orient_matrix_UB_13      -0.0324441000
_diffrn_orient_matrix_UB_21      0.0204706000
_diffrn_orient_matrix_UB_22      0.0565947000
_diffrn_orient_matrix_UB_23      0.0494130000
_diffrn_orient_matrix_UB_31      0.0498374000
_diffrn_orient_matrix_UB_32      -0.0503263000
_diffrn_orient_matrix_UB_33      0.0197663000
_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_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                825
_reflns_number_total             1907
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.477
_refine_diff_density_min         -0.606
_refine_diff_density_rms         0.100
_refine_ls_extinction_coef       0.0060(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   0.952
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     149
_refine_ls_number_reflns         1907
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1695
_refine_ls_R_factor_gt           0.0777
_refine_ls_restrained_S_all      0.952
_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)+(0.0887P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1738
_refine_ls_wR_factor_ref         0.2287
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Others
 Sof(O2B)=Sof(H2B)=Sof(H7B)=1-FVAR(1)
 Sof(O2)=Sof(H2)=Sof(H7A)=FVAR(1)
3.a Ternary CH refined with riding coordinates:
 C7(H7A), C7(H7B), C9(H9)
3.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
3.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C6(H6)
3.d Tetrahedral OH refined with riding coordinates:
 O2B(H2B)
3.e Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
3.f Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_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 0.81728(9) 0.02920(13) 0.40281(12) 0.1057(7) Uani 1 1 d . . . . .
F1 F 1.0311(5) 0.4782(8) 0.7196(6) 0.121(2) Uani 1 1 d . . . . .
O1 O 0.5827(5) 0.4841(7) 0.3019(7) 0.081(2) Uani 1 1 d . . . . .
O2 O 0.4735(9) 0.5859(18) 0.1349(11) 0.088(5) Uani 0.511(14) 1 d . . P A 1
H2 H 0.431514 0.629550 0.168667 0.132 Uiso 0.511(14) 1 calc R U P A 1
O2B O 0.6137(10) 0.7635(16) 0.2351(13) 0.093(5) Uani 0.489(14) 1 d . . P A 2
H2B H 0.617792 0.818144 0.175982 0.139 Uiso 0.489(14) 1 calc R U P A 2
N1 N 0.6682(5) 0.3494(8) 0.3182(6) 0.0636(18) Uani 1 1 d . . . . .
C1 C 0.7641(6) 0.3915(10) 0.4193(7) 0.059(2) Uani 1 1 d . . . . .
C2 C 0.8397(6) 0.2585(10) 0.4687(8) 0.067(2) Uani 1 1 d . . . . .
C3 C 0.9285(7) 0.2870(12) 0.5710(9) 0.077(3) Uani 1 1 d . . . . .
H3 H 0.978212 0.193514 0.606722 0.092 Uiso 1 1 calc R U . . .
C4 C 0.9426(8) 0.4516(14) 0.6187(9) 0.083(3) Uani 1 1 d . . . . .
C5 C 0.8691(8) 0.5860(12) 0.5730(10) 0.085(3) Uani 1 1 d . . . . .
H5 H 0.879905 0.699341 0.609464 0.102 Uiso 1 1 calc R U . . .
C6 C 0.7800(7) 0.5556(10) 0.4744(9) 0.076(3) Uani 1 1 d . . . . .
H6 H 0.727999 0.648141 0.442958 0.091 Uiso 1 1 calc R U . . .
C7 C 0.5821(8) 0.6027(15) 0.2061(9) 0.091(4) Uani 1 1 d . . . . .
H7A H 0.597476 0.727284 0.235508 0.110 Uiso 0.511(14) 1 calc R U P A 1
H7B H 0.508734 0.599441 0.141270 0.110 Uiso 0.489(14) 1 calc R U P A 2
C8 C 0.6729(9) 0.5374(15) 0.1653(12) 0.107(4) Uani 1 1 d . . . . .
H8A H 0.741811 0.606959 0.200960 0.128 Uiso 1 1 calc R U . . .
H8B H 0.651201 0.544678 0.078633 0.128 Uiso 1 1 calc R U . . .
C9 C 0.6894(7) 0.3443(13) 0.2067(9) 0.083(3) Uani 1 1 d . . . . .
H9 H 0.768169 0.307607 0.220316 0.100 Uiso 1 1 calc R U . . .
C10 C 0.6092(8) 0.2144(15) 0.1205(9) 0.103(4) Uani 1 1 d . . . . .
H10A H 0.621569 0.094328 0.153301 0.154 Uiso 1 1 calc R U . . .
H10B H 0.622749 0.216353 0.045121 0.154 Uiso 1 1 calc R U . . .
H10C H 0.532168 0.250118 0.108292 0.154 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 C2 1.884(8) . ?
F1 C4 1.371(11) . ?
O1 N1 1.454(8) . ?
O1 C7 1.458(12) . ?
O2 H2 0.8400 . ?
O2 C7 1.370(13) . ?
O2B H2B 0.8400 . ?
O2B C7 1.289(15) . ?
N1 C1 1.446(9) . ?
N1 C9 1.457(12) . ?
C1 C2 1.381(10) . ?
C1 C6 1.387(11) . ?
C2 C3 1.385(12) . ?
C3 H3 0.9500 . ?
C3 C4 1.355(12) . ?
C4 C5 1.366(13) . ?
C5 H5 0.9500 . ?
C5 C6 1.362(12) . ?
C6 H6 0.9500 . ?
C7 H7A 1.0000 . ?
C7 H7B 1.0000 . ?
C7 C8 1.484(16) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.530(13) . ?
C9 H9 1.0000 . ?
C9 C10 1.542(13) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?

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
N1 O1 C7 110.0(7) . . ?
C7 O2 H2 109.5 . . ?
C7 O2B H2B 109.5 . . ?
O1 N1 C9 104.7(6) . . ?
C1 N1 O1 110.2(6) . . ?
C1 N1 C9 114.8(7) . . ?
C2 C1 N1 118.5(7) . . ?
C2 C1 C6 118.2(7) . . ?
C6 C1 N1 123.2(7) . . ?
C1 C2 Br1 119.9(6) . . ?
C1 C2 C3 121.1(8) . . ?
C3 C2 Br1 118.8(6) . . ?
C2 C3 H3 120.8 . . ?
C4 C3 C2 118.3(8) . . ?
C4 C3 H3 120.8 . . ?
C3 C4 F1 117.7(9) . . ?
C3 C4 C5 122.2(9) . . ?
C5 C4 F1 120.0(10) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 C4 119.2(9) . . ?
C6 C5 H5 120.4 . . ?
C1 C6 H6 119.5 . . ?
C5 C6 C1 121.0(8) . . ?
C5 C6 H6 119.5 . . ?
O1 C7 H7A 110.3 . . ?
O1 C7 H7B 111.2 . . ?
O1 C7 C8 105.0(7) . . ?
O2 C7 O1 100.3(10) . . ?
O2 C7 H7A 110.3 . . ?
O2 C7 C8 119.8(12) . . ?
O2B C7 O1 116.3(11) . . ?
O2B C7 H7B 111.2 . . ?
O2B C7 C8 101.2(10) . . ?
C8 C7 H7A 110.3 . . ?
C8 C7 H7B 111.2 . . ?
C7 C8 H8A 110.9 . . ?
C7 C8 H8B 110.9 . . ?
C7 C8 C9 104.3(9) . . ?
H8A C8 H8B 108.9 . . ?
C9 C8 H8A 110.9 . . ?
C9 C8 H8B 110.9 . . ?
N1 C9 C8 103.2(9) . . ?
N1 C9 H9 109.8 . . ?
N1 C9 C10 110.7(8) . . ?
C8 C9 H9 109.8 . . ?
C8 C9 C10 113.3(9) . . ?
C10 C9 H9 109.8 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

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 C3 C4 -178.8(8) . . . . ?
F1 C4 C5 C6 -178.2(10) . . . . ?
O1 N1 C1 C2 162.0(8) . . . . ?
O1 N1 C1 C6 -13.2(12) . . . . ?
O1 N1 C9 C8 33.8(8) . . . . ?
O1 N1 C9 C10 -87.7(8) . . . . ?
O1 C7 C8 C9 21.8(11) . . . . ?
O2 C7 C8 C9 -89.6(13) . . . . ?
O2B C7 C8 C9 143.3(10) . . . . ?
N1 O1 C7 O2 123.8(9) . . . . ?
N1 O1 C7 O2B -112.1(10) . . . . ?
N1 O1 C7 C8 -1.1(10) . . . . ?
N1 C1 C2 Br1 0.7(12) . . . . ?
N1 C1 C2 C3 -175.0(9) . . . . ?
N1 C1 C6 C5 176.8(9) . . . . ?
C1 N1 C9 C8 -87.2(8) . . . . ?
C1 N1 C9 C10 151.3(7) . . . . ?
C1 C2 C3 C4 -3.1(15) . . . . ?
C2 C1 C6 C5 1.5(14) . . . . ?
C2 C3 C4 F1 -179.7(9) . . . . ?
C2 C3 C4 C5 3.7(16) . . . . ?
C3 C4 C5 C6 -1.8(17) . . . . ?
C4 C5 C6 C1 -0.9(16) . . . . ?
C6 C1 C2 Br1 176.3(7) . . . . ?
C6 C1 C2 C3 0.6(14) . . . . ?
C7 O1 N1 C1 102.8(8) . . . . ?
C7 O1 N1 C9 -21.2(8) . . . . ?
C7 C8 C9 N1 -34.8(10) . . . . ?
C7 C8 C9 C10 84.9(11) . . . . ?
C9 N1 C1 C2 -80.0(10) . . . . ?
C9 N1 C1 C6 104.7(10) . . . . ?

_olex2_date_sample_data_collection 2023-12-08
_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 15.001
_oxdiff_exptl_absorpt_empirical_full_min 0.209
