# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
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data_10
_database_code_depnum_ccdc_archive 'CCDC 2113745'
loop_
_audit_author_name
_audit_author_address
'Kenta Kato'
;Waseda University
Japan
;
_audit_update_record             
;
2021-11-04 deposited with the CCDC.	2021-12-21 downloaded from the CCDC.
;
_audit_creation_date             2021-09-27
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.07.19 svn.r715e62df for OlexSys, GUI svn.r6380)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H9 Br F N3 O'
_chemical_formula_sum            'C12 H9 Br F N3 O'
_chemical_formula_weight         310.13
_chemical_absolute_configuration ad
_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 0.0181 0.0091 '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 -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   8.0916(6)
_cell_length_b                   6.0738(5)
_cell_length_c                   12.9097(10)
_cell_angle_alpha                90
_cell_angle_beta                 105.671(7)
_cell_angle_gamma                90
_cell_volume                     610.89(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4610
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      136.47
_cell_measurement_theta_min      7.11
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.651
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.6435
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'JABSCOR (Rigaku, 1995)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.686
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             308
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0427
_diffrn_reflns_av_unetI/netI     0.0383
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7095
_diffrn_reflns_point_group_measured_fraction_full 0.953
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_theta_full        67.680
_diffrn_reflns_theta_max         68.228
_diffrn_reflns_theta_min         3.556
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 10
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  RAPID
_diffrn_measurement_method       'w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.5418
_diffrn_source                   ?
_diffrn_source_current           100.0
_diffrn_source_power             5.0
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.725
_reflns_Friedel_fraction_full    0.894
_reflns_Friedel_fraction_max     0.890
_reflns_number_gt                2108
_reflns_number_total             2127
_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       'Rigaku RAPID-AUTO'
_computing_data_collection       'Rigaku RAPID-AUTO'
_computing_data_reduction        'Rigaku RAPID-AUTO'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.405
_refine_diff_density_min         -1.047
_refine_diff_density_rms         0.151
_refine_ls_abs_structure_details 
;
 Flack x determined using 868 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.031(11)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.148
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2127
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0324
_refine_ls_R_factor_gt           0.0323
_refine_ls_restrained_S_all      1.147
_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)+(0.0554P)²+0.0210P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0846
_refine_ls_wR_factor_ref         0.0847
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C2(H2), C5(H5), C3(H3), C11(H11), C10(H10), C12(H12)
1.b X=CH2 refined with riding coordinates:
 N1(H1A,H1B)
;
_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 0.84769(5) 0.14938(9) 0.38712(3) 0.0392(2) Uani 1 1 d . . . . .
F1 F 0.5869(3) 0.8080(4) 0.73109(16) 0.0192(5) Uani 1 1 d . . . . .
O1 O 0.9038(4) 0.5131(6) 0.9184(2) 0.0311(7) Uani 1 1 d . . . . .
N2 N 0.4475(5) 0.6022(6) 0.8637(2) 0.0263(8) Uani 1 1 d . . . . .
N1 N 0.8502(4) 0.8787(8) 0.8859(2) 0.0281(9) Uani 1 1 d . . . . .
H1A H 0.934514 0.920653 0.941054 0.034 Uiso 1 1 calc R U . . .
H1B H 0.785250 0.977883 0.844365 0.034 Uiso 1 1 calc R U . . .
N3 N 0.5282(5) 0.2657(6) 0.8001(3) 0.0335(9) Uani 1 1 d . . . . .
C9 C 0.5375(5) 0.4801(6) 0.8134(3) 0.0185(8) Uani 1 1 d . . . . .
C8 C 0.8210(4) 0.6669(10) 0.8656(3) 0.0209(8) Uani 1 1 d . . . . .
C6 C 0.8599(5) 0.2063(7) 0.6075(3) 0.0258(9) Uani 1 1 d . . . . .
H6 H 0.929529 0.077892 0.618501 0.031 Uiso 1 1 calc R U . . .
C2 C 0.6975(5) 0.4808(8) 0.4880(3) 0.0251(9) Uani 1 1 d . . . . .
H2 H 0.657706 0.539994 0.417519 0.030 Uiso 1 1 calc R U . . .
C5 C 0.8216(5) 0.3120(7) 0.6935(3) 0.0224(8) Uani 1 1 d . . . . .
H5 H 0.866060 0.255652 0.764237 0.027 Uiso 1 1 calc R U . . .
C4 C 0.7194(5) 0.4986(6) 0.6775(3) 0.0167(7) Uani 1 1 d . . . . .
C3 C 0.6583(5) 0.5836(6) 0.5738(3) 0.0216(8) Uani 1 1 d . . . . .
H3 H 0.589460 0.712742 0.562152 0.026 Uiso 1 1 calc R U . . .
C7 C 0.6672(5) 0.6095(6) 0.7699(3) 0.0162(8) Uani 1 1 d . . . . .
C1 C 0.7945(5) 0.2924(7) 0.5057(3) 0.0235(8) Uani 1 1 d . . . . .
C11 C 0.2987(6) 0.2750(8) 0.8831(3) 0.0273(9) Uani 1 1 d . . . . .
H11 H 0.208998 0.203501 0.904707 0.033 Uiso 1 1 calc R U . . .
C10 C 0.3277(6) 0.4967(9) 0.8979(3) 0.0309(11) Uani 1 1 d . . . . .
H10 H 0.259789 0.578270 0.933946 0.037 Uiso 1 1 calc R U . . .
C12 C 0.4060(6) 0.1607(10) 0.8354(4) 0.0378(10) Uani 1 1 d . . . . .
H12 H 0.394022 0.005616 0.827226 0.045 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 C1 1.907(4) . ?
F1 C7 1.397(4) . ?
O1 C8 1.240(6) . ?
N2 C9 1.325(5) . ?
N2 C10 1.333(6) . ?
N1 H1A 0.8800 . ?
N1 H1B 0.8800 . ?
N1 C8 1.322(8) . ?
N3 C9 1.313(5) . ?
N3 C12 1.355(6) . ?
C9 C7 1.535(5) . ?
C8 C7 1.539(5) . ?
C6 H6 0.9500 . ?
C6 C5 1.388(5) . ?
C6 C1 1.381(6) . ?
C2 H2 0.9500 . ?
C2 C3 1.381(5) . ?
C2 C1 1.372(6) . ?
C5 H5 0.9500 . ?
C5 C4 1.385(6) . ?
C4 C3 1.395(5) . ?
C4 C7 1.526(5) . ?
C3 H3 0.9500 . ?
C11 H11 0.9500 . ?
C11 C10 1.371(7) . ?
C11 C12 1.380(6) . ?
C10 H10 0.9500 . ?
C12 H12 0.9500 . ?

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
C9 N2 C10 116.0(4) . . ?
H1A N1 H1B 120.0 . . ?
C8 N1 H1A 120.0 . . ?
C8 N1 H1B 120.0 . . ?
C9 N3 C12 116.4(4) . . ?
N2 C9 C7 114.4(3) . . ?
N3 C9 N2 126.8(4) . . ?
N3 C9 C7 118.7(3) . . ?
O1 C8 N1 125.7(4) . . ?
O1 C8 C7 118.1(5) . . ?
N1 C8 C7 116.2(4) . . ?
C5 C6 H6 120.8 . . ?
C1 C6 H6 120.8 . . ?
C1 C6 C5 118.4(4) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C1 C2 C3 119.3(4) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 C6 120.8(4) . . ?
C4 C5 H5 119.6 . . ?
C5 C4 C3 119.3(3) . . ?
C5 C4 C7 121.6(3) . . ?
C3 C4 C7 119.0(3) . . ?
C2 C3 C4 120.2(4) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
F1 C7 C9 106.0(3) . . ?
F1 C7 C8 106.8(3) . . ?
F1 C7 C4 107.5(3) . . ?
C9 C7 C8 107.9(3) . . ?
C4 C7 C9 114.9(3) . . ?
C4 C7 C8 113.2(3) . . ?
C6 C1 Br1 118.7(3) . . ?
C2 C1 Br1 119.3(3) . . ?
C2 C1 C6 121.9(4) . . ?
C10 C11 H11 121.6 . . ?
C10 C11 C12 116.8(5) . . ?
C12 C11 H11 121.6 . . ?
N2 C10 C11 122.6(4) . . ?
N2 C10 H10 118.7 . . ?
C11 C10 H10 118.7 . . ?
N3 C12 C11 121.2(5) . . ?
N3 C12 H12 119.4 . . ?
C11 C12 H12 119.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C8 C7 F1 174.3(3) . . . . ?
O1 C8 C7 C9 60.8(4) . . . . ?
O1 C8 C7 C4 -67.5(4) . . . . ?
N2 C9 C7 F1 -38.4(4) . . . . ?
N2 C9 C7 C8 75.7(4) . . . . ?
N2 C9 C7 C4 -157.1(3) . . . . ?
N1 C8 C7 F1 -3.8(4) . . . . ?
N1 C8 C7 C9 -117.4(3) . . . . ?
N1 C8 C7 C4 114.3(4) . . . . ?
N3 C9 C7 F1 142.9(4) . . . . ?
N3 C9 C7 C8 -103.0(5) . . . . ?
N3 C9 C7 C4 24.3(5) . . . . ?
C9 N2 C10 C11 0.4(7) . . . . ?
C9 N3 C12 C11 -0.3(7) . . . . ?
C6 C5 C4 C3 -1.7(6) . . . . ?
C6 C5 C4 C7 176.4(4) . . . . ?
C5 C6 C1 Br1 179.6(3) . . . . ?
C5 C6 C1 C2 1.8(6) . . . . ?
C5 C4 C3 C2 0.9(6) . . . . ?
C5 C4 C7 F1 171.5(3) . . . . ?
C5 C4 C7 C9 -70.7(4) . . . . ?
C5 C4 C7 C8 53.8(5) . . . . ?
C3 C2 C1 Br1 179.7(3) . . . . ?
C3 C2 C1 C6 -2.5(6) . . . . ?
C3 C4 C7 F1 -10.4(4) . . . . ?
C3 C4 C7 C9 107.4(4) . . . . ?
C3 C4 C7 C8 -128.1(4) . . . . ?
C7 C4 C3 C2 -177.2(3) . . . . ?
C1 C6 C5 C4 0.4(6) . . . . ?
C1 C2 C3 C4 1.1(6) . . . . ?
C10 N2 C9 N3 -4.6(7) . . . . ?
C10 N2 C9 C7 176.8(3) . . . . ?
C10 C11 C12 N3 -3.3(7) . . . . ?
C12 N3 C9 N2 4.6(7) . . . . ?
C12 N3 C9 C7 -176.9(4) . . . . ?
C12 C11 C10 N2 3.3(7) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
