# Electronic Supplementary Material (ESI) for Molecular Systems Design & Engineering.
# This journal is © The Royal Society of Chemistry 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. 
# 
#######################################################################

data_comp_1
_database_code_depnum_ccdc_archive 'CCDC 2306305'
loop_
_audit_author_name
_audit_author_address
"simone d'agostino"
;university of bologna
Italy
;
_audit_update_record             
;
2023-11-07 deposited with the CCDC.	2024-05-31 downloaded from the CCDC.
;
_audit_creation_date             2023-01-18
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        BrSA
_chemical_formula_moiety         'C13 H10 Br N O'
_chemical_formula_sum            'C13 H10 Br N O'
_chemical_formula_weight         276.13
_chemical_absolute_configuration unk
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C13 H10 Br1 O N'
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      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y, z+1/2'
'x+1/2, -y, z'

_cell_length_a                   6.2262(3)
_cell_length_b                   7.0317(4)
_cell_length_c                   26.2485(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1149.18(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    966
_cell_measurement_temperature    298.00
_cell_measurement_theta_max      22.6860
_cell_measurement_theta_min      2.8970
_shelx_estimated_absorpt_T_max   0.718
_shelx_estimated_absorpt_T_min   0.270
_exptl_absorpt_coefficient_mu    3.553
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66793
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.75a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.596
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_av_unetI/netI     0.0456
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.865
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3124
_diffrn_reflns_point_group_measured_fraction_full 0.676
_diffrn_reflns_point_group_measured_fraction_max 0.560
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         29.007
_diffrn_reflns_theta_min         2.897
_diffrn_ambient_temperature      298.00
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1385
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.865
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     28.00  54.00   1.00   32.50    --  -16.52   0.00-150.00   26
  2  ω    -62.00  23.00   1.00   32.50    --  -16.52   0.00-150.00   85
  3  ω     -1.00  26.00   1.00   32.50    --   17.46  77.00  90.00   27
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0056501000
_diffrn_orient_matrix_UB_12      -0.0196535000
_diffrn_orient_matrix_UB_13      -0.0264758000
_diffrn_orient_matrix_UB_21      0.0884801000
_diffrn_orient_matrix_UB_22      -0.0629297000
_diffrn_orient_matrix_UB_23      0.0023064000
_diffrn_orient_matrix_UB_31      -0.0715478000
_diffrn_orient_matrix_UB_32      -0.0763059000
_diffrn_orient_matrix_UB_33      0.0049287000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.267
_reflns_Friedel_fraction_full    0.336
_reflns_Friedel_fraction_max     0.241
_reflns_number_gt                1198
_reflns_number_total             1714
_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 1.171.42.75a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.75a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.75a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.461
_refine_diff_density_min         -0.369
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details 
;
 Flack x determined using 236 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.028(15)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         1714
_refine_ls_number_restraints     118
_refine_ls_R_factor_all          0.0764
_refine_ls_R_factor_gt           0.0462
_refine_ls_restrained_S_all      1.016
_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)+(0.0324P)²+0.2139P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0776
_refine_ls_wR_factor_ref         0.0868
_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. Rigid body (RIGU) restrains
 C4, Br1, C11, C10, C12, C9, H10, H12, C13, C8, H9, H13, N1, C7, C1, H7, C2,
 C6, C3, O1, C5, H6, H3, H1, H5, H4
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C7(H7)
3.b Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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 -0.19730(11) -0.20507(10) -0.19669(5) 0.0749(3) Uani 1 1 d . . . . .
C1 C -0.6677(10) -0.2845(8) 0.0972(2) 0.0376(14) Uani 1 1 d . . . . .
C2 C -0.8772(14) -0.2106(10) 0.1008(4) 0.0452(18) Uani 1 1 d . . . . .
C3 C -0.9664(15) -0.1766(11) 0.1480(3) 0.052(2) Uani 1 1 d . . . . .
H3 H -1.110(11) -0.132(8) 0.151(2) 0.031(18) Uiso 1 1 d . . . . .
C4 C -0.8592(14) -0.2234(11) 0.1911(3) 0.056(2) Uani 1 1 d . . . . .
H4 H -0.923521 -0.201837 0.222596 0.067 Uiso 1 1 calc R U . . .
C5 C -0.6562(15) -0.3025(13) 0.1893(3) 0.055(2) Uani 1 1 d . . . . .
H5 H -0.583(14) -0.353(12) 0.215(4) 0.10(3) Uiso 1 1 d . . . . .
C6 C -0.5623(12) -0.3302(9) 0.1426(3) 0.0470(17) Uani 1 1 d . . . . .
H6 H -0.417(9) -0.384(7) 0.140(2) 0.035(16) Uiso 1 1 d . . . . .
C7 C -0.5611(12) -0.3039(7) 0.0489(3) 0.0391(15) Uani 1 1 d . . . . .
H7 H -0.418191 -0.342239 0.048292 0.047 Uiso 1 1 calc R U . . .
C8 C -0.5393(13) -0.2649(9) -0.0398(3) 0.0377(15) Uani 1 1 d . . . . .
C9 C -0.3350(12) -0.1895(10) -0.0431(3) 0.0414(16) Uani 1 1 d . . . . .
H9 H -0.278(10) -0.137(9) -0.017(3) 0.05(2) Uiso 1 1 d . . . . .
C10 C -0.2346(11) -0.1718(9) -0.0898(3) 0.0447(16) Uani 1 1 d . . . . .
H10 H -0.102(10) -0.111(8) -0.090(2) 0.06(2) Uiso 1 1 d . . . . .
C11 C -0.3391(12) -0.2305(9) -0.1330(3) 0.0464(16) Uani 1 1 d . . . . .
C12 C -0.5408(13) -0.3070(10) -0.1307(3) 0.0479(18) Uani 1 1 d . . . . .
H12 H -0.595(9) -0.338(7) -0.159(2) 0.035(17) Uiso 1 1 d . . . . .
C13 C -0.6435(13) -0.3230(9) -0.0846(3) 0.0414(18) Uani 1 1 d . . . . .
H13 H -0.790(13) -0.381(11) -0.081(3) 0.08(3) Uiso 1 1 d . . . . .
N1 N -0.6576(12) -0.2698(9) 0.0064(3) 0.0416(15) Uani 1 1 d . . . . .
O1 O -0.9915(8) -0.1678(7) 0.05877(19) 0.0565(13) Uani 1 1 d . . . . .
H1 H -0.914894 -0.178632 0.033525 0.085 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 C11 1.899(7) . ?
C1 C2 1.407(10) . ?
C1 C6 1.397(9) . ?
C1 C7 1.438(10) . ?
C2 C3 1.381(11) . ?
C2 O1 1.346(10) . ?
C3 H3 0.95(7) . ?
C3 C4 1.354(12) . ?
C4 H4 0.9300 . ?
C4 C5 1.382(13) . ?
C5 H5 0.90(9) . ?
C5 C6 1.373(10) . ?
C6 H6 0.98(5) . ?
C7 H7 0.9300 . ?
C7 N1 1.290(10) . ?
C8 C9 1.381(11) . ?
C8 C13 1.405(10) . ?
C8 N1 1.419(10) . ?
C9 H9 0.85(7) . ?
C9 C10 1.380(10) . ?
C10 H10 0.93(6) . ?
C10 C11 1.371(9) . ?
C11 C12 1.368(10) . ?
C12 H12 0.84(6) . ?
C12 C13 1.373(10) . ?
C13 H13 1.00(8) . ?
O1 H1 0.8200 . ?

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 C7 121.4(6) . . ?
C6 C1 C2 117.7(7) . . ?
C6 C1 C7 120.9(6) . . ?
C3 C2 C1 119.8(8) . . ?
O1 C2 C1 121.2(7) . . ?
O1 C2 C3 119.0(7) . . ?
C2 C3 H3 121(4) . . ?
C4 C3 C2 120.7(9) . . ?
C4 C3 H3 118(4) . . ?
C3 C4 H4 119.3 . . ?
C3 C4 C5 121.3(8) . . ?
C5 C4 H4 119.3 . . ?
C4 C5 H5 127(6) . . ?
C6 C5 C4 118.5(8) . . ?
C6 C5 H5 114(6) . . ?
C1 C6 H6 118(3) . . ?
C5 C6 C1 122.0(7) . . ?
C5 C6 H6 120(3) . . ?
C1 C7 H7 119.0 . . ?
N1 C7 C1 122.0(7) . . ?
N1 C7 H7 119.0 . . ?
C9 C8 C13 118.9(7) . . ?
C9 C8 N1 122.8(7) . . ?
C13 C8 N1 118.0(7) . . ?
C8 C9 H9 120(4) . . ?
C10 C9 C8 120.6(7) . . ?
C10 C9 H9 119(4) . . ?
C9 C10 H10 117(4) . . ?
C11 C10 C9 119.5(7) . . ?
C11 C10 H10 123(4) . . ?
C10 C11 Br1 118.7(5) . . ?
C12 C11 Br1 120.2(5) . . ?
C12 C11 C10 121.2(7) . . ?
C11 C12 H12 116(4) . . ?
C11 C12 C13 119.9(7) . . ?
C13 C12 H12 124(4) . . ?
C8 C13 H13 117(5) . . ?
C12 C13 C8 119.9(7) . . ?
C12 C13 H13 123(5) . . ?
C7 N1 C8 120.1(7) . . ?
C2 O1 H1 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 C11 C12 C13 -179.3(5) . . . . ?
C1 C2 C3 C4 -3.7(11) . . . . ?
C1 C7 N1 C8 171.2(6) . . . . ?
C2 C1 C6 C5 -0.8(9) . . . . ?
C2 C1 C7 N1 -5.8(9) . . . . ?
C2 C3 C4 C5 1.4(12) . . . . ?
C3 C4 C5 C6 1.1(13) . . . . ?
C4 C5 C6 C1 -1.4(12) . . . . ?
C6 C1 C2 C3 3.4(9) . . . . ?
C6 C1 C2 O1 -178.2(7) . . . . ?
C6 C1 C7 N1 177.2(6) . . . . ?
C7 C1 C2 C3 -173.6(7) . . . . ?
C7 C1 C2 O1 4.7(10) . . . . ?
C7 C1 C6 C5 176.2(7) . . . . ?
C8 C9 C10 C11 -0.2(10) . . . . ?
C9 C8 C13 C12 1.0(10) . . . . ?
C9 C8 N1 C7 -37.8(11) . . . . ?
C9 C10 C11 Br1 -179.9(5) . . . . ?
C9 C10 C11 C12 -0.3(10) . . . . ?
C10 C11 C12 C13 1.1(11) . . . . ?
C11 C12 C13 C8 -1.5(10) . . . . ?
C13 C8 C9 C10 -0.1(10) . . . . ?
C13 C8 N1 C7 148.4(6) . . . . ?
N1 C8 C9 C10 -173.9(7) . . . . ?
N1 C8 C13 C12 175.0(7) . . . . ?
O1 C2 C3 C4 177.9(7) . . . . ?

_olex2_submission_original_sample_id BrSA
_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 1.251
_oxdiff_exptl_absorpt_empirical_full_min 0.762
####################################################################### 
# 
# 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_comp_2
_database_code_depnum_ccdc_archive 'CCDC 2306306'
loop_
_audit_author_name
_audit_author_address
"simone d'agostino"
;university of bologna
Italy
;
_audit_update_record             
;
2023-11-07 deposited with the CCDC.	2024-05-31 downloaded from the CCDC.
;
_audit_creation_date             2023-06-14
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H8 Br F2 N O'
_chemical_formula_sum            'C13 H8 Br F2 N O'
_chemical_formula_weight         312.11
_chemical_absolute_configuration ?
_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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   5.4360(9)
_cell_length_b                   19.728(3)
_cell_length_c                   5.8339(10)
_cell_angle_alpha                90
_cell_angle_beta                 105.561(17)
_cell_angle_gamma                90
_cell_volume                     602.69(18)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1147
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.2500
_cell_measurement_theta_min      3.6350
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.421
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68521
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.75a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.720
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             308
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1271
_diffrn_reflns_av_unetI/netI     0.2000
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.857
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            4760
_diffrn_reflns_point_group_measured_fraction_full 0.849
_diffrn_reflns_point_group_measured_fraction_max 0.687
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         29.411
_diffrn_reflns_theta_min         2.065
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1385
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.857
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -28.00  12.00   1.00   75.00    --  -16.52 -77.00 -30.00   40
  2  ω    -45.00  35.00   1.00   75.00    --  -16.52  77.00  90.00   80
  3  ω      1.00  34.00   1.00   75.00    --   17.46  77.00-120.00   33
  4  ω    -53.00  55.00   1.00   75.00    --   17.46 -19.00 150.00  108
  5  ω    -10.00  18.00   1.00   75.00    --   17.46  77.00-150.00   28
  6  ω     -1.00  86.00   1.00   75.00    --   17.46  57.00 -30.00   87
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0624476000
_diffrn_orient_matrix_UB_12      -0.0300149000
_diffrn_orient_matrix_UB_13      0.0213276000
_diffrn_orient_matrix_UB_21      -0.1139270000
_diffrn_orient_matrix_UB_22      0.0107583000
_diffrn_orient_matrix_UB_23      -0.0831978000
_diffrn_orient_matrix_UB_31      0.0383936000
_diffrn_orient_matrix_UB_32      -0.0165980000
_diffrn_orient_matrix_UB_33      -0.0925073000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.561
_reflns_Friedel_fraction_full    0.689
_reflns_Friedel_fraction_max     0.507
_reflns_number_gt                850
_reflns_number_total             2288
_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 1.171.42.75a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.75a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.75a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXD  (Sheldrick, 2008)'
_refine_diff_density_max         0.987
_refine_diff_density_min         -0.408
_refine_diff_density_rms         0.117
_refine_ls_abs_structure_details 
;
 Flack x determined using 262 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.772
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2288
_refine_ls_number_restraints     136
_refine_ls_R_factor_all          0.1746
_refine_ls_R_factor_gt           0.0654
_refine_ls_restrained_S_all      0.753
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1536
_refine_ls_wR_factor_ref         0.1830
_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. Rigid body (RIGU) restrains
 Br1, C1, C2, C3, H3, C4, H4, C5, H5, C6, H6, C7, H7, C8, C9, H9, C10, C11,
 C12, H12, C13, F1, F2, N1, O1
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C9(H9), C12(H12)
3.b Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_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 -0.0714(3) -0.68134(11) -0.1204(3) 0.0821(6) Uani 1 1 d . . . . .
C1 C -0.974(3) -0.9814(8) 0.260(3) 0.062(4) Uani 1 1 d . . . . .
C2 C -0.874(4) -0.9978(10) 0.489(3) 0.066(5) Uani 1 1 d . . . . .
C3 C -1.001(4) -1.0502(10) 0.595(3) 0.082(5) Uani 1 1 d . . . . .
H3 H -0.933143 -1.065178 0.750531 0.098 Uiso 1 1 calc R U . . .
C4 C -1.224(4) -1.0756(9) 0.453(4) 0.085(5) Uani 1 1 d . . . . .
H4 H -1.310459 -1.107353 0.520193 0.102 Uiso 1 1 calc R U . . .
C5 C -1.328(4) -1.0585(10) 0.225(4) 0.084(5) Uani 1 1 d . . . . .
H5 H -1.477537 -1.078609 0.134149 0.101 Uiso 1 1 calc R U . . .
C6 C -1.200(3) -1.0088(8) 0.131(3) 0.073(4) Uani 1 1 d . . . . .
H6 H -1.270914 -0.993777 -0.023926 0.087 Uiso 1 1 calc R U . . .
C7 C -0.851(3) -0.9295(8) 0.148(3) 0.061(4) Uani 1 1 d . . . . .
H7 H -0.921011 -0.918425 -0.010780 0.073 Uiso 1 1 calc R U . . .
C8 C -0.527(3) -0.8490(8) 0.163(2) 0.053(3) Uani 1 1 d . . . . .
C9 C -0.616(3) -0.8236(9) -0.067(3) 0.059(4) Uani 1 1 d . . . . .
H9 H -0.765415 -0.840437 -0.168287 0.071 Uiso 1 1 calc R U . . .
C10 C -0.480(3) -0.7729(8) -0.144(3) 0.059(3) Uani 1 1 d . . . . .
C11 C -0.249(3) -0.7497(8) -0.004(3) 0.061(4) Uani 1 1 d . . . . .
C12 C -0.158(3) -0.7733(8) 0.219(3) 0.064(4) Uani 1 1 d . . . . .
H12 H -0.009279 -0.755373 0.318598 0.077 Uiso 1 1 calc R U . . .
C13 C -0.289(3) -0.8245(8) 0.300(2) 0.053(3) Uani 1 1 d . . . . .
F1 F -0.1999(18) -0.8478(6) 0.5193(17) 0.083(3) Uani 1 1 d . . . . .
F2 F -0.5704(17) -0.7478(5) -0.3675(16) 0.082(3) Uani 1 1 d . . . . .
N1 N -0.649(2) -0.8992(7) 0.267(2) 0.064(3) Uani 1 1 d . . . . .
O1 O -0.659(2) -0.9718(8) 0.6312(18) 0.092(4) Uani 1 1 d . . . . .
H1 H -0.591859 -0.946529 0.553979 0.138 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 C11 1.886(16) . ?
C1 C2 1.34(2) . ?
C1 C6 1.37(2) . ?
C1 C7 1.47(2) . ?
C2 C3 1.47(3) . ?
C2 O1 1.34(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.37(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.34(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.40(2) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C7 N1 1.277(17) . ?
C8 C9 1.392(19) . ?
C8 C13 1.414(19) . ?
C8 N1 1.415(19) . ?
C9 H9 0.9300 . ?
C9 C10 1.39(2) . ?
C10 C11 1.38(2) . ?
C10 F2 1.358(17) . ?
C11 C12 1.35(2) . ?
C12 H12 0.9300 . ?
C12 C13 1.39(2) . ?
C13 F1 1.323(16) . ?
O1 H1 0.8200 . ?

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 121.0(16) . . ?
C2 C1 C7 120.1(14) . . ?
C6 C1 C7 118.7(14) . . ?
C1 C2 C3 118.8(18) . . ?
C1 C2 O1 125.3(17) . . ?
O1 C2 C3 115.9(16) . . ?
C2 C3 H3 121.9 . . ?
C4 C3 C2 116.2(18) . . ?
C4 C3 H3 121.9 . . ?
C3 C4 H4 117.3 . . ?
C5 C4 C3 125.3(18) . . ?
C5 C4 H4 117.3 . . ?
C4 C5 H5 121.9 . . ?
C4 C5 C6 116.3(18) . . ?
C6 C5 H5 121.9 . . ?
C1 C6 C5 122.1(17) . . ?
C1 C6 H6 119.0 . . ?
C5 C6 H6 119.0 . . ?
C1 C7 H7 119.6 . . ?
N1 C7 C1 120.9(14) . . ?
N1 C7 H7 119.6 . . ?
C9 C8 C13 116.6(14) . . ?
C9 C8 N1 125.8(14) . . ?
C13 C8 N1 117.5(13) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 C8 119.7(14) . . ?
C10 C9 H9 120.1 . . ?
C11 C10 C9 121.8(15) . . ?
F2 C10 C9 119.1(14) . . ?
F2 C10 C11 119.0(15) . . ?
C10 C11 Br1 119.8(12) . . ?
C12 C11 Br1 120.4(12) . . ?
C12 C11 C10 119.7(15) . . ?
C11 C12 H12 120.2 . . ?
C11 C12 C13 119.6(14) . . ?
C13 C12 H12 120.2 . . ?
C12 C13 C8 122.2(14) . . ?
F1 C13 C8 118.0(14) . . ?
F1 C13 C12 119.6(14) . . ?
C7 N1 C8 121.9(13) . . ?
C2 O1 H1 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 C11 C12 C13 -178.7(11) . . . . ?
C1 C2 C3 C4 -4(3) . . . . ?
C1 C7 N1 C8 179.9(13) . . . . ?
C2 C1 C6 C5 -5(3) . . . . ?
C2 C1 C7 N1 0(2) . . . . ?
C2 C3 C4 C5 3(3) . . . . ?
C3 C4 C5 C6 -2(3) . . . . ?
C4 C5 C6 C1 3(3) . . . . ?
C6 C1 C2 C3 5(3) . . . . ?
C6 C1 C2 O1 -177.4(18) . . . . ?
C6 C1 C7 N1 175.1(14) . . . . ?
C7 C1 C2 C3 -179.8(16) . . . . ?
C7 C1 C2 O1 -2(3) . . . . ?
C7 C1 C6 C5 179.9(16) . . . . ?
C8 C9 C10 C11 4(2) . . . . ?
C8 C9 C10 F2 -178.9(12) . . . . ?
C9 C8 C13 C12 5.7(19) . . . . ?
C9 C8 C13 F1 179.9(13) . . . . ?
C9 C8 N1 C7 4(2) . . . . ?
C9 C10 C11 Br1 179.4(12) . . . . ?
C9 C10 C11 C12 -4(2) . . . . ?
C10 C11 C12 C13 5(2) . . . . ?
C11 C12 C13 C8 -6(2) . . . . ?
C11 C12 C13 F1 180.0(14) . . . . ?
C13 C8 C9 C10 -5(2) . . . . ?
C13 C8 N1 C7 -172.4(13) . . . . ?
F2 C10 C11 Br1 2.5(19) . . . . ?
F2 C10 C11 C12 178.9(13) . . . . ?
N1 C8 C9 C10 178.4(14) . . . . ?
N1 C8 C13 C12 -177.2(13) . . . . ?
N1 C8 C13 F1 -2.9(18) . . . . ?
O1 C2 C3 C4 178.3(17) . . . . ?

_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 2.126
_oxdiff_exptl_absorpt_empirical_full_min 0.772
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
_oxdiff_twin_reflns_isolated
_oxdiff_twin_reflns_overlapped
_twin_individual_twin_lattice_type
_twin_individual_twin_matrix_11
_twin_individual_twin_matrix_12
_twin_individual_twin_matrix_13
_twin_individual_twin_matrix_21
_twin_individual_twin_matrix_22
_twin_individual_twin_matrix_23
_twin_individual_twin_matrix_31
_twin_individual_twin_matrix_32
_twin_individual_twin_matrix_33
1 0.6132 4624 175 ref 1.0000 0.0000 0.0000 0.0000 1.0000 0.0000 0.0000 0.0000
1.0000
2 0.3868 4604 175 nmt -0.6009 -0.1931 -0.5630 -2.6234 0.2078 1.5009 -0.2563
0.2520 -0.5750

_twin_special_details            
;
Component 2 rotated by -168.2027° 
around [-0.18 0.97 0.19] (reciprocal) or [-0.70 0.36 0.62] (direct)
;
####################################################################### 
# 
# 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_comp_3
_database_code_depnum_ccdc_archive 'CCDC 2306307'
loop_
_audit_author_name
_audit_author_address
"simone d'agostino"
;university of bologna
Italy
;
_audit_update_record             
;
2023-11-07 deposited with the CCDC.	2024-05-31 downloaded from the CCDC.
;
_audit_creation_date             2023-06-14
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        Br3,5FSA_irr
_chemical_formula_moiety         'C13 H8 Br F2 N O'
_chemical_formula_sum            'C13 H8 Br F2 N O'
_chemical_formula_weight         312.11
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.9293(12)
_cell_length_b                   7.4667(9)
_cell_length_c                   12.746(2)
_cell_angle_alpha                74.781(13)
_cell_angle_beta                 84.546(14)
_cell_angle_gamma                69.627(14)
_cell_volume                     596.53(17)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1336
_cell_measurement_temperature    293.00
_cell_measurement_theta_max      25.7190
_cell_measurement_theta_min      3.0120
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.457
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75784
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.75a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.738
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             308
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_unetI/netI     0.0628
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.821
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4559
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.821
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         29.452
_diffrn_reflns_theta_min         3.002
_diffrn_ambient_temperature      293.00
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1385
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.821
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -45.00  37.00   1.00   66.50    --  -16.68  77.00-150.00   82
  2  ω    -25.00   8.00   1.00   66.50    --  -16.68 -77.00  90.00   33
  3  ω     -7.00  34.00   1.00   66.50    --   17.62  77.00 -30.00   41
  4  ω    -52.00  50.00   1.00   66.50    --   17.62 -19.00 -90.00  102
  5  ω     -1.00  86.00   1.00   66.50    --   17.62  57.00  90.00   87
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0902876000
_diffrn_orient_matrix_UB_12      -0.0241168000
_diffrn_orient_matrix_UB_13      -0.0321275000
_diffrn_orient_matrix_UB_21      0.0128117000
_diffrn_orient_matrix_UB_22      -0.1015433000
_diffrn_orient_matrix_UB_23      0.0196329000
_diffrn_orient_matrix_UB_31      -0.0600600000
_diffrn_orient_matrix_UB_32      0.0060314000
_diffrn_orient_matrix_UB_33      -0.0436849000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1734
_reflns_number_total             2731
_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 1.171.42.75a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.75a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.75a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.479
_refine_diff_density_min         -0.305
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         2731
_refine_ls_number_restraints     135
_refine_ls_R_factor_all          0.0979
_refine_ls_R_factor_gt           0.0518
_refine_ls_restrained_S_all      1.012
_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)+(0.0343P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0848
_refine_ls_wR_factor_ref         0.1001
_refine_special_details          ?
_olex2_refinement_description    
;
1. Rigid body (RIGU) restrains
 C4, Br1, C11, C10, C12, C9, F1, C13, F2, C8, H9, H13, N1, C7, C1, H7, C2, C6,
 C3, O1, C5, H6, H3, H1, H5, H4
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
;
_atom_sites_solution_hydrogens   difmap
_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 0.87728(7) 0.67140(7) 0.87088(3) 0.0749(2) Uani 1 1 d . . . . .
C1 C 0.3867(6) 0.7667(6) 0.2823(3) 0.0508(9) Uani 1 1 d . . . . .
C2 C 0.1743(6) 0.8176(6) 0.2828(3) 0.0553(10) Uani 1 1 d . . . . .
C3 C 0.0755(8) 0.8330(7) 0.1888(4) 0.0701(13) Uani 1 1 d . . . . .
H3 H -0.066(7) 0.869(6) 0.197(3) 0.079(15) Uiso 1 1 d . . . . .
C4 C 0.1836(9) 0.8004(7) 0.0986(4) 0.0767(14) Uani 1 1 d . . . . .
H4 H 0.117(6) 0.807(6) 0.038(3) 0.074(12) Uiso 1 1 d . . . . .
C5 C 0.3931(10) 0.7497(8) 0.0961(4) 0.0884(16) Uani 1 1 d . . . . .
H5 H 0.471(8) 0.721(8) 0.033(4) 0.12(2) Uiso 1 1 d . . . . .
C6 C 0.4954(9) 0.7315(8) 0.1865(3) 0.0815(15) Uani 1 1 d . . . . .
H6 H 0.639(8) 0.701(8) 0.190(4) 0.12(2) Uiso 1 1 d . . . . .
C7 C 0.4994(7) 0.7468(6) 0.3771(3) 0.0545(10) Uani 1 1 d . . . . .
H7 H 0.642(6) 0.713(6) 0.367(3) 0.081(14) Uiso 1 1 d . . . . .
C8 C 0.5313(5) 0.7484(5) 0.5573(3) 0.0416(8) Uani 1 1 d . . . . .
C9 C 0.7424(6) 0.6876(6) 0.5586(3) 0.0526(10) Uani 1 1 d . . . . .
H9 H 0.831(6) 0.666(6) 0.498(3) 0.073(13) Uiso 1 1 d . . . . .
C10 C 0.8390(6) 0.6666(6) 0.6521(3) 0.0556(10) Uani 1 1 d . . . . .
C11 C 0.7359(6) 0.7039(5) 0.7455(3) 0.0493(9) Uani 1 1 d . . . . .
C12 C 0.5260(6) 0.7662(6) 0.7408(3) 0.0556(10) Uani 1 1 d . . . . .
C13 C 0.4222(6) 0.7883(6) 0.6489(3) 0.0524(10) Uani 1 1 d . . . . .
H13 H 0.280(6) 0.835(5) 0.652(3) 0.054(11) Uiso 1 1 d . . . . .
F1 F 1.0462(4) 0.6052(5) 0.6523(2) 0.0934(9) Uani 1 1 d . . . . .
F2 F 0.4173(4) 0.8050(5) 0.83001(18) 0.0994(10) Uani 1 1 d . . . . .
N1 N 0.4133(4) 0.7715(4) 0.4666(2) 0.0439(7) Uani 1 1 d . . . . .
O1 O 0.0628(5) 0.8497(5) 0.3723(3) 0.0788(10) Uani 1 1 d . . . . .
H1 H 0.132(8) 0.839(8) 0.419(4) 0.10(2) Uiso 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
Br1 C11 1.872(3) . ?
C1 C2 1.386(5) . ?
C1 C6 1.409(6) . ?
C1 C7 1.447(5) . ?
C2 C3 1.396(5) . ?
C2 O1 1.342(5) . ?
C3 H3 0.93(4) . ?
C3 C4 1.340(7) . ?
C4 H4 0.92(4) . ?
C4 C5 1.366(7) . ?
C5 H5 0.95(5) . ?
C5 C6 1.362(6) . ?
C6 H6 0.94(5) . ?
C7 H7 0.93(4) . ?
C7 N1 1.264(5) . ?
C8 C9 1.373(5) . ?
C8 C13 1.372(5) . ?
C8 N1 1.418(4) . ?
C9 H9 0.95(4) . ?
C9 C10 1.369(5) . ?
C10 C11 1.371(5) . ?
C10 F1 1.347(4) . ?
C11 C12 1.365(5) . ?
C12 C13 1.376(5) . ?
C12 F2 1.342(4) . ?
C13 H13 0.92(4) . ?
O1 H1 0.77(5) . ?

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 118.6(4) . . ?
C2 C1 C7 122.1(4) . . ?
C6 C1 C7 119.3(4) . . ?
C1 C2 C3 119.1(4) . . ?
O1 C2 C1 121.2(3) . . ?
O1 C2 C3 119.6(4) . . ?
C2 C3 H3 112(3) . . ?
C4 C3 C2 120.7(5) . . ?
C4 C3 H3 127(3) . . ?
C3 C4 H4 120(3) . . ?
C3 C4 C5 121.2(4) . . ?
C5 C4 H4 119(3) . . ?
C4 C5 H5 122(3) . . ?
C6 C5 C4 119.8(5) . . ?
C6 C5 H5 119(3) . . ?
C1 C6 H6 115(3) . . ?
C5 C6 C1 120.5(5) . . ?
C5 C6 H6 124(3) . . ?
C1 C7 H7 114(2) . . ?
N1 C7 C1 123.0(4) . . ?
N1 C7 H7 123(2) . . ?
C9 C8 N1 124.4(3) . . ?
C13 C8 C9 119.5(3) . . ?
C13 C8 N1 116.1(3) . . ?
C8 C9 H9 126(2) . . ?
C10 C9 C8 118.9(4) . . ?
C10 C9 H9 115(2) . . ?
C9 C10 C11 123.4(4) . . ?
F1 C10 C9 118.2(4) . . ?
F1 C10 C11 118.4(3) . . ?
C10 C11 Br1 121.3(3) . . ?
C12 C11 Br1 122.6(3) . . ?
C12 C11 C10 116.1(3) . . ?
C11 C12 C13 122.6(4) . . ?
F2 C12 C11 118.6(3) . . ?
F2 C12 C13 118.8(4) . . ?
C8 C13 C12 119.5(4) . . ?
C8 C13 H13 123(2) . . ?
C12 C13 H13 117(2) . . ?
C7 N1 C8 120.7(3) . . ?
C2 O1 H1 111(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 C11 C12 C13 -179.4(3) . . . . ?
Br1 C11 C12 F2 -0.2(5) . . . . ?
C1 C2 C3 C4 -0.4(7) . . . . ?
C1 C7 N1 C8 179.4(3) . . . . ?
C2 C1 C6 C5 0.8(7) . . . . ?
C2 C1 C7 N1 1.0(6) . . . . ?
C2 C3 C4 C5 0.5(7) . . . . ?
C3 C4 C5 C6 0.0(8) . . . . ?
C4 C5 C6 C1 -0.7(8) . . . . ?
C6 C1 C2 C3 -0.3(6) . . . . ?
C6 C1 C2 O1 178.9(4) . . . . ?
C6 C1 C7 N1 -178.3(4) . . . . ?
C7 C1 C2 C3 -179.6(4) . . . . ?
C7 C1 C2 O1 -0.5(6) . . . . ?
C7 C1 C6 C5 -179.8(5) . . . . ?
C8 C9 C10 C11 -0.2(6) . . . . ?
C8 C9 C10 F1 179.5(3) . . . . ?
C9 C8 C13 C12 -0.2(6) . . . . ?
C9 C8 N1 C7 -4.1(6) . . . . ?
C9 C10 C11 Br1 179.8(3) . . . . ?
C9 C10 C11 C12 -0.5(6) . . . . ?
C10 C11 C12 C13 0.9(6) . . . . ?
C10 C11 C12 F2 -180.0(4) . . . . ?
C11 C12 C13 C8 -0.6(6) . . . . ?
C13 C8 C9 C10 0.6(6) . . . . ?
C13 C8 N1 C7 176.8(4) . . . . ?
F1 C10 C11 Br1 0.1(5) . . . . ?
F1 C10 C11 C12 179.8(3) . . . . ?
F2 C12 C13 C8 -179.7(4) . . . . ?
N1 C8 C9 C10 -178.5(3) . . . . ?
N1 C8 C13 C12 179.0(3) . . . . ?
O1 C2 C3 C4 -179.5(4) . . . . ?

_olex2_submission_original_sample_id Br3_5FSAirr
_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 1.433
_oxdiff_exptl_absorpt_empirical_full_min 0.836
####################################################################### 
# 
# 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_comp_4
_database_code_depnum_ccdc_archive 'CCDC 2306308'
loop_
_audit_author_name
_audit_author_address
"simone d'agostino"
;university of bologna
Italy
;
_audit_update_record             
;
2023-11-07 deposited with the CCDC.	2024-05-31 downloaded from the CCDC.
;
_audit_creation_date             2023-01-18
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        2,6_Sa
_chemical_formula_moiety         'C13 H8 Br F2 N O'
_chemical_formula_sum            'C13 H8 Br F2 N O'
_chemical_formula_weight         312.11
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.2141(6)
_cell_length_b                   7.5974(6)
_cell_length_c                   11.6575(8)
_cell_angle_alpha                79.343(6)
_cell_angle_beta                 79.021(6)
_cell_angle_gamma                71.454(7)
_cell_volume                     589.33(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1961
_cell_measurement_temperature    298
_cell_measurement_theta_max      24.8140
_cell_measurement_theta_min      2.8570
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.499
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59717
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.75a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.759
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             308
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_av_unetI/netI     0.0524
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6198
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         27.021
_diffrn_reflns_theta_min         2.854
_diffrn_ambient_temperature      298
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1385
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -55.00 -30.00   1.00    8.50    --  -16.68 122.00-135.00   25
  2  ω    -75.00 -50.00   1.00    8.50    --  -16.68 152.00  24.00   25
  3  ω     16.00  89.00   1.00    8.50    --   17.46-152.00 -17.00   73
  4  ω     31.00  68.00   1.00    8.50    --   17.46-122.00 142.00   37
  5  ω    -35.00  52.00   1.00    8.50    --  -16.68  57.00   0.00   87
  6  ω    -49.00   1.00   1.00    8.50    --  -16.68 -57.00-150.00   50
  7  ω    -84.00 -50.00   1.00    8.50    --  -16.68 -57.00-150.00   34
  8  ω    -17.00  23.00   1.00    8.50    --  -16.68 -99.00-180.00   40
  9  ω      4.00  54.00   1.00    8.50    --  -16.68  38.00  60.00   50
 10  ω      3.00  79.00   1.00    8.50    --   17.46  57.00 150.00   76
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0163910000
_diffrn_orient_matrix_UB_12      0.0013199000
_diffrn_orient_matrix_UB_13      -0.0620685000
_diffrn_orient_matrix_UB_21      -0.0932873000
_diffrn_orient_matrix_UB_22      0.0677941000
_diffrn_orient_matrix_UB_23      -0.0040938000
_diffrn_orient_matrix_UB_31      0.0447563000
_diffrn_orient_matrix_UB_32      0.0726347000
_diffrn_orient_matrix_UB_33      -0.0064819000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1826
_reflns_number_total             2521
_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 1.171.42.75a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.75a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.75a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.291
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       0.0042(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         2521
_refine_ls_number_restraints     135
_refine_ls_R_factor_all          0.0811
_refine_ls_R_factor_gt           0.0514
_refine_ls_restrained_S_all      1.068
_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)+(0.0309P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0803
_refine_ls_wR_factor_ref         0.0897
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All O(H) groups
2. Rigid body (RIGU) restrains
 C1, Br1, C11, C10, C12, C9, H10, C13, H12, F003, C8, F002, N1, C7, H7, C6, C2,
  C5, H6, O1, C3, C4, H5, H1, H3, H4
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3.a Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   mixed
_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 0.11564(6) 0.71069(5) 0.01904(4) 0.0704(2) Uani 1 1 d . . . . .
C1 C 0.6118(5) 0.1269(4) 0.6230(3) 0.0416(8) Uani 1 1 d . . . . .
C2 C 0.4596(5) 0.0784(4) 0.7048(3) 0.0465(8) Uani 1 1 d . . . . .
C3 C 0.4992(7) -0.0142(5) 0.8167(4) 0.0570(10) Uani 1 1 d . . . . .
H3 H 0.394(6) -0.047(5) 0.869(3) 0.085(13) Uiso 1 1 d . . . . .
C4 C 0.6847(7) -0.0588(5) 0.8467(4) 0.0598(10) Uani 1 1 d . . . . .
H4 H 0.707(6) -0.129(6) 0.924(4) 0.096(14) Uiso 1 1 d . . . . .
C5 C 0.8361(6) -0.0133(5) 0.7666(4) 0.0568(10) Uani 1 1 d . . . . .
H5 H 0.961(5) -0.050(4) 0.783(3) 0.054(10) Uiso 1 1 d . . . . .
C6 C 0.7972(6) 0.0783(5) 0.6570(3) 0.0503(9) Uani 1 1 d . . . . .
H6 H 0.894(5) 0.112(4) 0.603(3) 0.059(11) Uiso 1 1 d . . . . .
C7 C 0.5761(6) 0.2252(4) 0.5068(3) 0.0451(8) Uani 1 1 d . . . . .
H7 H 0.690(6) 0.245(4) 0.456(3) 0.071(12) Uiso 1 1 d . . . . .
C8 C 0.3546(5) 0.3751(4) 0.3669(3) 0.0391(7) Uani 1 1 d . . . . .
C9 C 0.4722(5) 0.4474(4) 0.2724(3) 0.0462(8) Uani 1 1 d . . . . .
C10 C 0.4073(5) 0.5446(5) 0.1697(3) 0.0469(8) Uani 1 1 d . . . . .
H10 H 0.498(5) 0.588(4) 0.108(3) 0.056(10) Uiso 1 1 d . . . . .
C11 C 0.2135(5) 0.5740(4) 0.1585(3) 0.0455(8) Uani 1 1 d . . . . .
C12 C 0.0875(6) 0.5076(5) 0.2469(3) 0.0468(8) Uani 1 1 d . . . . .
H12 H -0.036(5) 0.526(4) 0.239(3) 0.049(10) Uiso 1 1 d . . . . .
C13 C 0.1610(5) 0.4111(4) 0.3477(3) 0.0431(8) Uani 1 1 d . . . . .
F002 F 0.0383(3) 0.3438(3) 0.43489(17) 0.0609(6) Uani 1 1 d . . . . .
F003 F 0.6626(3) 0.4202(3) 0.28296(19) 0.0734(6) Uani 1 1 d . . . . .
N1 N 0.4052(4) 0.2766(3) 0.4760(2) 0.0431(7) Uani 1 1 d . . . . .
O1 O 0.2763(4) 0.1168(4) 0.6786(2) 0.0641(7) Uani 1 1 d . . . . .
H1 H 0.271881 0.168953 0.610535 0.096 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 C11 1.889(3) . ?
C1 C2 1.407(5) . ?
C1 C6 1.384(5) . ?
C1 C7 1.448(5) . ?
C2 C3 1.397(5) . ?
C2 O1 1.343(4) . ?
C3 H3 0.94(4) . ?
C3 C4 1.368(6) . ?
C4 H4 0.97(4) . ?
C4 C5 1.384(5) . ?
C5 H5 0.90(3) . ?
C5 C6 1.370(5) . ?
C6 H6 0.91(4) . ?
C7 H7 0.95(4) . ?
C7 N1 1.270(4) . ?
C8 C9 1.397(4) . ?
C8 C13 1.388(4) . ?
C8 N1 1.401(4) . ?
C9 C10 1.365(4) . ?
C9 F003 1.349(4) . ?
C10 H10 0.96(3) . ?
C10 C11 1.372(5) . ?
C11 C12 1.373(5) . ?
C12 H12 0.88(3) . ?
C12 C13 1.368(4) . ?
C13 F002 1.354(3) . ?
O1 H1 0.8200 . ?

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 C7 121.2(3) . . ?
C6 C1 C2 118.0(3) . . ?
C6 C1 C7 120.8(3) . . ?
C3 C2 C1 119.5(3) . . ?
O1 C2 C1 122.0(3) . . ?
O1 C2 C3 118.5(3) . . ?
C2 C3 H3 117(3) . . ?
C4 C3 C2 120.5(4) . . ?
C4 C3 H3 122(2) . . ?
C3 C4 H4 118(3) . . ?
C3 C4 C5 120.6(4) . . ?
C5 C4 H4 122(3) . . ?
C4 C5 H5 121(2) . . ?
C6 C5 C4 119.0(4) . . ?
C6 C5 H5 119(2) . . ?
C1 C6 H6 117(2) . . ?
C5 C6 C1 122.5(4) . . ?
C5 C6 H6 121(2) . . ?
C1 C7 H7 115(2) . . ?
N1 C7 C1 121.4(3) . . ?
N1 C7 H7 124(2) . . ?
C9 C8 N1 128.9(3) . . ?
C13 C8 C9 113.7(3) . . ?
C13 C8 N1 117.3(3) . . ?
C10 C9 C8 124.4(3) . . ?
F003 C9 C8 118.1(3) . . ?
F003 C9 C10 117.5(3) . . ?
C9 C10 H10 119(2) . . ?
C9 C10 C11 117.9(3) . . ?
C11 C10 H10 123(2) . . ?
C10 C11 Br1 119.5(3) . . ?
C10 C11 C12 121.6(3) . . ?
C12 C11 Br1 118.9(3) . . ?
C11 C12 H12 121(2) . . ?
C13 C12 C11 117.8(3) . . ?
C13 C12 H12 121(2) . . ?
C12 C13 C8 124.6(3) . . ?
F002 C13 C8 117.2(3) . . ?
F002 C13 C12 118.2(3) . . ?
C7 N1 C8 125.9(3) . . ?
C2 O1 H1 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 C11 C12 C13 -179.1(2) . . . . ?
C1 C2 C3 C4 -0.5(5) . . . . ?
C1 C7 N1 C8 178.8(3) . . . . ?
C2 C1 C6 C5 -0.4(5) . . . . ?
C2 C1 C7 N1 2.4(5) . . . . ?
C2 C3 C4 C5 -0.1(6) . . . . ?
C3 C4 C5 C6 0.5(5) . . . . ?
C4 C5 C6 C1 -0.2(5) . . . . ?
C6 C1 C2 C3 0.7(4) . . . . ?
C6 C1 C2 O1 -178.7(3) . . . . ?
C6 C1 C7 N1 -177.3(3) . . . . ?
C7 C1 C2 C3 -179.1(3) . . . . ?
C7 C1 C2 O1 1.5(5) . . . . ?
C7 C1 C6 C5 179.4(3) . . . . ?
C8 C9 C10 C11 0.2(5) . . . . ?
C9 C8 C13 C12 0.1(5) . . . . ?
C9 C8 C13 F002 179.3(2) . . . . ?
C9 C8 N1 C7 -4.2(5) . . . . ?
C9 C10 C11 Br1 179.1(2) . . . . ?
C9 C10 C11 C12 -0.4(5) . . . . ?
C10 C11 C12 C13 0.4(5) . . . . ?
C11 C12 C13 C8 -0.2(5) . . . . ?
C11 C12 C13 F002 -179.5(3) . . . . ?
C13 C8 C9 C10 -0.1(5) . . . . ?
C13 C8 C9 F003 179.7(3) . . . . ?
C13 C8 N1 C7 177.0(3) . . . . ?
F003 C9 C10 C11 -179.6(3) . . . . ?
N1 C8 C9 C10 -178.9(3) . . . . ?
N1 C8 C9 F003 0.9(5) . . . . ?
N1 C8 C13 C12 179.0(3) . . . . ?
N1 C8 C13 F002 -1.7(4) . . . . ?
O1 C2 C3 C4 179.0(3) . . . . ?

_olex2_date_sample_completion    2022-12-02
_olex2_date_sample_data_collection 2022-12-02
_olex2_submission_original_sample_id 2,6Sa
_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 1.570
_oxdiff_exptl_absorpt_empirical_full_min 0.771
####################################################################### 
# 
# 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_comp-5
_database_code_depnum_ccdc_archive 'CCDC 2306309'
loop_
_audit_author_name
_audit_author_address
"simone d'agostino"
;university of bologna
Italy
;
_audit_update_record             
;
2023-11-07 deposited with the CCDC.	2024-05-31 downloaded from the CCDC.
;
_audit_creation_date             2023-06-14
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H6 Br F4 N O'
_chemical_formula_sum            'C13 H6 Br F4 N O'
_chemical_formula_weight         348.10
_chemical_absolute_configuration ?
_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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   6.0196(6)
_cell_length_b                   7.4659(9)
_cell_length_c                   13.8518(9)
_cell_angle_alpha                90
_cell_angle_beta                 95.881(7)
_cell_angle_gamma                90
_cell_volume                     619.25(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    834
_cell_measurement_temperature    300
_cell_measurement_theta_max      24.3780
_cell_measurement_theta_min      4.0150
_shelx_estimated_absorpt_T_max   0.936
_shelx_estimated_absorpt_T_min   0.850
_exptl_absorpt_coefficient_mu    3.363
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54358
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.867
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             340
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0422
_diffrn_reflns_av_unetI/netI     0.0795
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.890
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            4719
_diffrn_reflns_point_group_measured_fraction_full 0.857
_diffrn_reflns_point_group_measured_fraction_max 0.720
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         29.028
_diffrn_reflns_theta_min         3.402
_diffrn_ambient_temperature      300
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1340
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.890
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -34.00  52.00   1.00   75.00    --  -16.52  57.00 120.00   86
  2  ω     -2.00  24.00   1.00   75.00    --  -16.52 -99.00   0.00   26
  3  ω    -21.00  10.00   1.00   75.00    --  -16.52 -99.00 150.00   31
  4  ω    -33.00  45.00   1.00   75.00    --  -16.52  57.00-120.00   78
  5  ω    -68.00 -43.00   1.00   75.00    --  -16.52-178.00  60.00   25
  6  ω     -5.00  21.00   1.00   75.00    --  -16.52 -99.00-120.00   26
  7  ω    -85.00  -4.00   1.00   75.00    --  -16.52 -57.00 -30.00   81
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1015841000
_diffrn_orient_matrix_UB_12      0.0480539000
_diffrn_orient_matrix_UB_13      0.0094247000
_diffrn_orient_matrix_UB_21      0.0472444000
_diffrn_orient_matrix_UB_22      -0.0506353000
_diffrn_orient_matrix_UB_23      -0.0360814000
_diffrn_orient_matrix_UB_31      -0.0385691000
_diffrn_orient_matrix_UB_32      0.0643780000
_diffrn_orient_matrix_UB_33      -0.0354969000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.508
_reflns_Friedel_fraction_full    0.692
_reflns_Friedel_fraction_max     0.524
_reflns_number_gt                1301
_reflns_number_total             2383
_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 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.430
_refine_diff_density_min         -0.371
_refine_diff_density_rms         0.060
_refine_ls_abs_structure_details 
;
 Flack x determined using 334 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.040(15)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         2383
_refine_ls_number_restraints     154
_refine_ls_R_factor_all          0.1198
_refine_ls_R_factor_gt           0.0504
_refine_ls_restrained_S_all      0.976
_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)+(0.0345P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0860
_refine_ls_wR_factor_ref         0.1100
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Rigid body (RIGU) restrains
 Br1, C1, C2, C3, H3, C4, H4, C5, H5, C6, H6, C7, H7, C8, C9, C10, C11, C12,
 C13, F1, F2, F3, F4, N1, O1, H1
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C7(H7)
;
_atom_sites_solution_hydrogens   mixed
_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 0.69282(15) 0.3159(2) 0.52556(5) 0.1025(5) Uani 1 1 d . . . . .
C1 C 1.0159(10) 0.2811(11) 1.1218(5) 0.0406(17) Uani 1 1 d . . . . .
C2 C 1.2318(10) 0.3404(13) 1.1475(5) 0.048(2) Uani 1 1 d . . . . .
C3 C 1.3113(12) 0.3582(11) 1.2452(6) 0.055(2) Uani 1 1 d . . . . .
H3 H 1.453222 0.404389 1.262591 0.066 Uiso 1 1 calc R U . . .
C4 C 1.1799(12) 0.3075(17) 1.3152(5) 0.062(2) Uani 1 1 d . . . . .
H4 H 1.233375 0.319196 1.380342 0.074 Uiso 1 1 calc R U . . .
C5 C 0.9683(13) 0.2390(10) 1.2905(5) 0.057(2) Uani 1 1 d . . . . .
H5 H 0.881973 0.200443 1.338449 0.068 Uiso 1 1 calc R U . . .
C6 C 0.8872(12) 0.2285(10) 1.1946(5) 0.051(2) Uani 1 1 d . . . . .
H6 H 0.743416 0.185378 1.177909 0.061 Uiso 1 1 calc R U . . .
C7 C 0.9253(11) 0.2647(9) 1.0220(5) 0.0436(19) Uani 1 1 d . . . . .
H7 H 0.780058 0.222760 1.008013 0.052 Uiso 1 1 calc R U . . .
C8 C 0.9424(10) 0.2991(13) 0.8549(4) 0.0400(15) Uani 1 1 d . . . . .
C9 C 0.7361(11) 0.3685(9) 0.8213(5) 0.0415(19) Uani 1 1 d . . . . .
C10 C 0.6635(11) 0.3743(11) 0.7248(5) 0.047(2) Uani 1 1 d . . . . .
C11 C 0.7925(11) 0.3093(16) 0.6572(4) 0.0507(17) Uani 1 1 d . . . . .
C12 C 0.9952(13) 0.2374(11) 0.6891(5) 0.053(2) Uani 1 1 d . . . . .
C13 C 1.0714(11) 0.2334(10) 0.7853(6) 0.0458(19) Uani 1 1 d . . . . .
F1 F 0.6077(6) 0.4415(6) 0.8846(3) 0.0544(12) Uani 1 1 d . . . . .
F2 F 0.4658(6) 0.4492(7) 0.6968(3) 0.0632(13) Uani 1 1 d . . . . .
F3 F 1.1286(8) 0.1672(8) 0.6250(4) 0.0777(15) Uani 1 1 d . . . . .
F4 F 1.2717(7) 0.1633(7) 0.8146(3) 0.0639(13) Uani 1 1 d . . . . .
N1 N 1.0387(8) 0.3062(11) 0.9518(4) 0.0470(14) Uani 1 1 d . . . . .
O1 O 1.3688(8) 0.3931(8) 1.0813(4) 0.0629(18) Uani 1 1 d . . . . .
H1 H 1.296(11) 0.378(11) 1.019(5) 0.07(3) Uiso 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
Br1 C11 1.862(6) . ?
C1 C2 1.385(9) . ?
C1 C6 1.389(9) . ?
C1 C7 1.438(9) . ?
C2 C3 1.394(9) . ?
C2 O1 1.353(8) . ?
C3 H3 0.9300 . ?
C3 C4 1.367(11) . ?
C4 H4 0.9300 . ?
C4 C5 1.382(10) . ?
C5 H5 0.9300 . ?
C5 C6 1.370(9) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C7 N1 1.282(8) . ?
C8 C9 1.382(8) . ?
C8 C13 1.389(9) . ?
C8 N1 1.407(7) . ?
C9 C10 1.364(9) . ?
C9 F1 1.343(7) . ?
C10 C11 1.365(10) . ?
C10 F2 1.336(7) . ?
C11 C12 1.364(10) . ?
C12 C13 1.363(10) . ?
C12 F3 1.362(9) . ?
C13 F4 1.338(7) . ?
O1 H1 0.93(7) . ?

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 118.8(6) . . ?
C2 C1 C7 121.9(6) . . ?
C6 C1 C7 119.2(6) . . ?
C1 C2 C3 120.0(7) . . ?
O1 C2 C1 122.7(6) . . ?
O1 C2 C3 117.2(7) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 C2 119.8(7) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 119.6 . . ?
C3 C4 C5 120.8(7) . . ?
C5 C4 H4 119.6 . . ?
C4 C5 H5 120.3 . . ?
C6 C5 C4 119.3(7) . . ?
C6 C5 H5 120.3 . . ?
C1 C6 H6 119.4 . . ?
C5 C6 C1 121.2(7) . . ?
C5 C6 H6 119.4 . . ?
C1 C7 H7 119.0 . . ?
N1 C7 C1 122.0(6) . . ?
N1 C7 H7 119.0 . . ?
C9 C8 C13 116.5(6) . . ?
C9 C8 N1 125.1(7) . . ?
C13 C8 N1 118.1(6) . . ?
C10 C9 C8 121.9(6) . . ?
F1 C9 C8 119.3(6) . . ?
F1 C9 C10 118.6(6) . . ?
C9 C10 C11 120.8(6) . . ?
F2 C10 C9 119.0(7) . . ?
F2 C10 C11 120.2(6) . . ?
C10 C11 Br1 120.9(6) . . ?
C12 C11 Br1 121.0(6) . . ?
C12 C11 C10 118.1(6) . . ?
C13 C12 C11 121.7(7) . . ?
F3 C12 C11 120.5(7) . . ?
F3 C12 C13 117.8(7) . . ?
C12 C13 C8 121.0(7) . . ?
F4 C13 C8 118.5(6) . . ?
F4 C13 C12 120.5(7) . . ?
C7 N1 C8 121.0(6) . . ?
C2 O1 H1 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 C11 C12 C13 179.3(7) . . . . ?
Br1 C11 C12 F3 -0.6(12) . . . . ?
C1 C2 C3 C4 3.6(14) . . . . ?
C1 C7 N1 C8 -176.3(7) . . . . ?
C2 C1 C6 C5 1.7(12) . . . . ?
C2 C1 C7 N1 -0.9(12) . . . . ?
C2 C3 C4 C5 -0.2(16) . . . . ?
C3 C4 C5 C6 -2.5(15) . . . . ?
C4 C5 C6 C1 1.7(12) . . . . ?
C6 C1 C2 C3 -4.4(12) . . . . ?
C6 C1 C2 O1 179.6(8) . . . . ?
C6 C1 C7 N1 -177.9(8) . . . . ?
C7 C1 C2 C3 178.5(8) . . . . ?
C7 C1 C2 O1 2.5(13) . . . . ?
C7 C1 C6 C5 178.9(7) . . . . ?
C8 C9 C10 C11 0.7(12) . . . . ?
C8 C9 C10 F2 -177.5(7) . . . . ?
C9 C8 C13 C12 -0.3(12) . . . . ?
C9 C8 C13 F4 -179.4(7) . . . . ?
C9 C8 N1 C7 46.8(13) . . . . ?
C9 C10 C11 Br1 179.6(6) . . . . ?
C9 C10 C11 C12 0.4(14) . . . . ?
C10 C11 C12 C13 -1.5(14) . . . . ?
C10 C11 C12 F3 178.6(8) . . . . ?
C11 C12 C13 C8 1.5(12) . . . . ?
C11 C12 C13 F4 -179.5(8) . . . . ?
C13 C8 C9 C10 -0.7(11) . . . . ?
C13 C8 C9 F1 -177.0(7) . . . . ?
C13 C8 N1 C7 -139.9(8) . . . . ?
F1 C9 C10 C11 177.0(8) . . . . ?
F1 C9 C10 F2 -1.2(10) . . . . ?
F2 C10 C11 Br1 -2.2(12) . . . . ?
F2 C10 C11 C12 178.6(8) . . . . ?
F3 C12 C13 C8 -178.6(7) . . . . ?
F3 C12 C13 F4 0.4(11) . . . . ?
N1 C8 C9 C10 172.7(8) . . . . ?
N1 C8 C9 F1 -3.6(12) . . . . ?
N1 C8 C13 C12 -174.3(8) . . . . ?
N1 C8 C13 F4 6.7(12) . . . . ?
O1 C2 C3 C4 179.8(9) . . . . ?

_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 1.549
_oxdiff_exptl_absorpt_empirical_full_min 0.782

# end

