# Electronic Supplementary Material (ESI) for ChemComm.
# 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_cxy1857_0m
_database_code_depnum_ccdc_archive 'CCDC 2154295'
loop_
_audit_author_name
_audit_author_address
'Henghui Li'
;Southern University of Science and Technology
China
;
_audit_update_record             
;
2022-02-24 deposited with the CCDC.	2022-03-10 downloaded from the CCDC.
;
_audit_creation_date             2021-12-17
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.10.07 svn.r9718050b for OlexSys, GUI svn.r6410)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H10 Br N O'
_chemical_formula_sum            'C12 H10 Br N O'
_chemical_formula_weight         264.12
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   7.127(2)
_cell_length_b                   7.435(3)
_cell_length_c                   10.981(4)
_cell_angle_alpha                72.738(11)
_cell_angle_beta                 84.610(12)
_cell_angle_gamma                67.998(12)
_cell_volume                     515.1(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2539
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.30
_cell_measurement_theta_min      3.08
_shelx_estimated_absorpt_T_max   0.648
_shelx_estimated_absorpt_T_min   0.315
_exptl_absorpt_coefficient_mu    3.959
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.3803
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1387 before and 0.0768 after correction.
The Ratio of minimum to maximum transmission is 0.5100.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.703
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             264
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0637
_diffrn_reflns_av_unetI/netI     0.0590
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_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       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8229
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.375
_diffrn_reflns_theta_min         3.081
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker PHOTON 100 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2269
_reflns_number_total             2560
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.844
_refine_diff_density_min         -0.734
_refine_diff_density_rms         0.112
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         2560
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0436
_refine_ls_R_factor_gt           0.0343
_refine_ls_restrained_S_all      1.061
_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)+(0.0348P)²+0.0750P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0790
_refine_ls_wR_factor_ref         0.0828
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C7(H7), C8(H8), C9(H9), C10(H10), C11(H11)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
2.c 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 0.88395(4) 0.31716(4) 0.93186(2) 0.01805(10) Uani 1 1 d . . . . .
O1 O 0.1841(3) 0.7365(3) 0.55327(17) 0.0181(4) Uani 1 1 d . . . . .
H1 H 0.214929 0.801890 0.483005 0.027 Uiso 1 1 calc R U . . .
N1 N 0.4117(3) 0.8684(3) 0.3859(2) 0.0137(4) Uani 1 1 d . . . . .
C1 C 0.2394(4) 1.0878(4) 0.1860(3) 0.0215(6) Uani 1 1 d . . . . .
H1A H 0.215692 0.992484 0.149699 0.032 Uiso 1 1 calc R U . . .
H1B H 0.254630 1.200065 0.116937 0.032 Uiso 1 1 calc R U . . .
H1C H 0.124210 1.140512 0.238280 0.032 Uiso 1 1 calc R U . . .
C2 C 0.4288(4) 0.9812(4) 0.2675(3) 0.0161(5) Uani 1 1 d . . . . .
C3 C 0.5753(4) 0.7680(4) 0.4655(2) 0.0129(5) Uani 1 1 d . . . . .
C4 C 0.5405(4) 0.6516(4) 0.5951(2) 0.0117(5) Uani 1 1 d . . . . .
C5 C 0.6999(4) 0.5492(4) 0.6865(2) 0.0134(5) Uani 1 1 d . . . . .
H5 H 0.831234 0.551129 0.663797 0.016 Uiso 1 1 calc R U . . .
C6 C 0.6667(4) 0.4465(4) 0.8084(2) 0.0149(5) Uani 1 1 d . . . . .
C7 C 0.4778(4) 0.4364(4) 0.8443(3) 0.0166(5) Uani 1 1 d . . . . .
H7 H 0.457241 0.364162 0.928478 0.020 Uiso 1 1 calc R U . . .
C8 C 0.7630(4) 0.7809(4) 0.4274(2) 0.0153(5) Uani 1 1 d . . . . .
H8 H 0.876732 0.711399 0.484125 0.018 Uiso 1 1 calc R U . . .
C9 C 0.7812(4) 0.8966(4) 0.3054(3) 0.0174(5) Uani 1 1 d . . . . .
H9 H 0.907917 0.907118 0.277578 0.021 Uiso 1 1 calc R U . . .
C10 C 0.6135(4) 0.9969(4) 0.2244(2) 0.0171(5) Uani 1 1 d . . . . .
H10 H 0.624315 1.075630 0.140215 0.020 Uiso 1 1 calc R U . . .
C11 C 0.3205(4) 0.5331(4) 0.7557(2) 0.0157(5) Uani 1 1 d . . . . .
H11 H 0.191332 0.525634 0.779312 0.019 Uiso 1 1 calc R U . . .
C12 C 0.3478(4) 0.6421(4) 0.6318(2) 0.0144(5) Uani 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 C6 1.915(3) . ?
O1 H1 0.8400 . ?
O1 C12 1.347(3) . ?
N1 C2 1.344(3) . ?
N1 C3 1.354(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C1 C2 1.502(4) . ?
C2 C10 1.391(4) . ?
C3 C4 1.482(4) . ?
C3 C8 1.394(3) . ?
C4 C5 1.410(3) . ?
C4 C12 1.416(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.379(4) . ?
C6 C7 1.390(4) . ?
C7 H7 0.9500 . ?
C7 C11 1.381(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.385(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.384(4) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C11 C12 1.400(4) . ?

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
C12 O1 H1 109.5 . . ?
C2 N1 C3 120.2(2) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
N1 C2 C1 116.5(2) . . ?
N1 C2 C10 121.0(2) . . ?
C10 C2 C1 122.5(2) . . ?
N1 C3 C4 116.3(2) . . ?
N1 C3 C8 121.0(2) . . ?
C8 C3 C4 122.7(2) . . ?
C5 C4 C3 120.4(2) . . ?
C5 C4 C12 118.0(2) . . ?
C12 C4 C3 121.6(2) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 C4 120.6(2) . . ?
C6 C5 H5 119.7 . . ?
C5 C6 Br1 119.53(19) . . ?
C5 C6 C7 121.4(2) . . ?
C7 C6 Br1 119.1(2) . . ?
C6 C7 H7 120.6 . . ?
C11 C7 C6 118.9(2) . . ?
C11 C7 H7 120.6 . . ?
C3 C8 H8 120.5 . . ?
C9 C8 C3 119.0(2) . . ?
C9 C8 H8 120.5 . . ?
C8 C9 H9 120.2 . . ?
C10 C9 C8 119.6(2) . . ?
C10 C9 H9 120.2 . . ?
C2 C10 H10 120.4 . . ?
C9 C10 C2 119.3(3) . . ?
C9 C10 H10 120.4 . . ?
C7 C11 H11 119.4 . . ?
C7 C11 C12 121.2(2) . . ?
C12 C11 H11 119.4 . . ?
O1 C12 C4 123.2(2) . . ?
O1 C12 C11 116.9(2) . . ?
C11 C12 C4 119.8(2) . . ?

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 C6 C7 C11 178.76(19) . . . . ?
N1 C2 C10 C9 -0.8(4) . . . . ?
N1 C3 C4 C5 -177.3(2) . . . . ?
N1 C3 C4 C12 1.6(3) . . . . ?
N1 C3 C8 C9 -0.7(4) . . . . ?
C1 C2 C10 C9 179.1(2) . . . . ?
C2 N1 C3 C4 178.6(2) . . . . ?
C2 N1 C3 C8 0.6(4) . . . . ?
C3 N1 C2 C1 -179.7(2) . . . . ?
C3 N1 C2 C10 0.2(4) . . . . ?
C3 C4 C5 C6 177.8(2) . . . . ?
C3 C4 C12 O1 -0.1(4) . . . . ?
C3 C4 C12 C11 -178.9(2) . . . . ?
C3 C8 C9 C10 0.1(4) . . . . ?
C4 C3 C8 C9 -178.6(2) . . . . ?
C4 C5 C6 Br1 -177.80(18) . . . . ?
C4 C5 C6 C7 1.5(4) . . . . ?
C5 C4 C12 O1 178.9(2) . . . . ?
C5 C4 C12 C11 0.0(4) . . . . ?
C5 C6 C7 C11 -0.5(4) . . . . ?
C6 C7 C11 C12 -0.7(4) . . . . ?
C7 C11 C12 O1 -178.0(2) . . . . ?
C7 C11 C12 C4 1.0(4) . . . . ?
C8 C3 C4 C5 0.6(4) . . . . ?
C8 C3 C4 C12 179.6(2) . . . . ?
C8 C9 C10 C2 0.7(4) . . . . ?
C12 C4 C5 C6 -1.2(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
