# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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 
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data_mo_220531_shiyuan_24br_0m
_database_code_depnum_ccdc_archive 'CCDC 2178804'
_audit_update_record             
;
2022-06-13 deposited with the CCDC.	2022-11-09 downloaded from the CCDC.
;
_audit_creation_date             2022-06-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H11 Br2 F3 N2 O'
_chemical_formula_sum            'C12 H11 Br2 F3 N2 O'
_chemical_formula_weight         416.05
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.9638(4)
_cell_length_b                   7.6176(2)
_cell_length_c                   16.0976(6)
_cell_angle_alpha                90
_cell_angle_beta                 111.5740(10)
_cell_angle_gamma                90
_cell_volume                     1364.28(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4918
_cell_measurement_temperature    169(2)
_cell_measurement_theta_max      27.10
_cell_measurement_theta_min      2.72
_shelx_estimated_absorpt_T_max   0.413
_shelx_estimated_absorpt_T_min   0.158
_exptl_absorpt_coefficient_mu    5.973
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.1566
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1487 before and 0.0684 after correction.
The Ratio of minimum to maximum transmission is 0.2101.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.026
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0580
_diffrn_reflns_av_unetI/netI     0.0644
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            9355
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.161
_diffrn_reflns_theta_min         2.663
_diffrn_ambient_temperature      169.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'zju Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2551
_reflns_number_total             3005
_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 V8.40B (Bruker Nano, Inc., 2019)'
_computing_data_collection       'Bruker Instrument Service vV6.2.14'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.152
_refine_diff_density_min         -1.985
_refine_diff_density_rms         0.269
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3005
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0567
_refine_ls_R_factor_gt           0.0494
_refine_ls_restrained_S_all      1.050
_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)+(0.0771P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1232
_refine_ls_wR_factor_ref         0.1276
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C5(H5)
;
_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 0.29401(4) 0.94984(5) 0.08104(3) 0.02480(16) Uani 1 1 d . . . . .
Br2 Br 0.61759(4) 0.97057(5) 0.43964(3) 0.02741(16) Uani 1 1 d . . . . .
F1 F 0.2329(2) 0.2187(3) 0.34180(19) 0.0356(6) Uani 1 1 d . . . . .
F2 F 0.3063(2) 0.3195(3) 0.24841(18) 0.0342(6) Uani 1 1 d . . . . .
F3 F 0.4087(2) 0.3348(3) 0.38849(19) 0.0374(6) Uani 1 1 d . . . . .
O1 O -0.0564(2) 0.9381(3) 0.3875(2) 0.0249(6) Uani 1 1 d . . . . .
N1 N 0.1565(3) 0.5300(4) 0.3573(2) 0.0176(6) Uani 1 1 d . . . . .
N2 N 0.1013(3) 0.6730(4) 0.3731(2) 0.0182(6) Uani 1 1 d . . . . .
C1 C 0.2782(3) 0.7338(4) 0.2195(2) 0.0178(7) Uani 1 1 d . . . . .
H1 H 0.211125 0.682553 0.173830 0.021 Uiso 1 1 calc R . . . .
C2 C 0.3427(3) 0.8679(5) 0.2000(2) 0.0176(7) Uani 1 1 d . . . . .
C3 C 0.4429(3) 0.9416(5) 0.2646(3) 0.0205(8) Uani 1 1 d . . . . .
H3 H 0.486199 1.033667 0.250205 0.025 Uiso 1 1 calc R . . . .
C4 C 0.4781(3) 0.8773(5) 0.3509(3) 0.0185(7) Uani 1 1 d . . . . .
C5 C 0.4147(3) 0.7454(5) 0.3736(2) 0.0171(7) Uani 1 1 d . . . . .
H5 H 0.439939 0.703727 0.433314 0.020 Uiso 1 1 calc R . . . .
C6 C 0.3136(3) 0.6753(4) 0.3076(2) 0.0157(7) Uani 1 1 d . . . . .
C7 C 0.2454(3) 0.5296(4) 0.3314(3) 0.0184(8) Uani 1 1 d . . . . .
C8 C 0.2967(3) 0.3500(5) 0.3277(3) 0.0238(8) Uani 1 1 d . . . . .
C9 C 0.1001(3) 0.8466(5) 0.3338(3) 0.0230(8) Uani 1 1 d . . . . .
H9A H 0.045904 0.845717 0.270226 0.028 Uiso 1 1 calc R . . . .
H9B H 0.181971 0.877232 0.336910 0.028 Uiso 1 1 calc R . . . .
C10 C 0.0571(4) 0.9812(5) 0.3847(3) 0.0272(9) Uani 1 1 d . . . . .
H10A H 0.116567 0.990020 0.446461 0.033 Uiso 1 1 calc R . . . .
H10B H 0.051991 1.097363 0.355937 0.033 Uiso 1 1 calc R . . . .
C11 C -0.0486(4) 0.7734(5) 0.4313(3) 0.0270(9) Uani 1 1 d . . . . .
H11A H -0.127361 0.744974 0.435075 0.032 Uiso 1 1 calc R . . . .
H11B H 0.011498 0.781492 0.492897 0.032 Uiso 1 1 calc R . . . .
C12 C -0.0132(3) 0.6293(5) 0.3819(3) 0.0250(8) Uani 1 1 d . . . . .
H12A H -0.005128 0.517322 0.414831 0.030 Uiso 1 1 calc R . . . .
H12B H -0.076324 0.614362 0.321927 0.030 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C2 1.891(4) . ?
Br2 C4 1.892(4) . ?
F1 C8 1.327(4) . ?
F2 C8 1.342(5) . ?
F3 C8 1.343(5) . ?
O1 C10 1.414(4) . ?
O1 C11 1.425(5) . ?
N1 N2 1.346(4) . ?
N1 C7 1.278(5) . ?
N2 C9 1.464(4) . ?
N2 C12 1.465(4) . ?
C1 H1 0.9500 . ?
C1 C2 1.385(5) . ?
C1 C6 1.395(5) . ?
C2 C3 1.385(5) . ?
C3 H3 0.9500 . ?
C3 C4 1.383(5) . ?
C4 C5 1.386(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.391(5) . ?
C6 C7 1.508(5) . ?
C7 C8 1.510(5) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.515(5) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.505(5) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?

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
C10 O1 C11 109.3(3) . . ?
C7 N1 N2 126.1(3) . . ?
N1 N2 C9 125.2(3) . . ?
N1 N2 C12 112.1(3) . . ?
C9 N2 C12 112.7(3) . . ?
C2 C1 H1 120.7 . . ?
C2 C1 C6 118.7(3) . . ?
C6 C1 H1 120.7 . . ?
C1 C2 Br1 118.9(3) . . ?
C1 C2 C3 122.0(3) . . ?
C3 C2 Br1 119.1(3) . . ?
C2 C3 H3 121.0 . . ?
C4 C3 C2 118.1(3) . . ?
C4 C3 H3 121.0 . . ?
C3 C4 Br2 118.9(3) . . ?
C3 C4 C5 121.8(3) . . ?
C5 C4 Br2 119.3(3) . . ?
C4 C5 H5 120.6 . . ?
C4 C5 C6 118.9(3) . . ?
C6 C5 H5 120.6 . . ?
C1 C6 C7 120.2(3) . . ?
C5 C6 C1 120.5(3) . . ?
C5 C6 C7 119.2(3) . . ?
N1 C7 C6 132.4(3) . . ?
N1 C7 C8 114.5(3) . . ?
C6 C7 C8 113.1(3) . . ?
F1 C8 F2 106.7(3) . . ?
F1 C8 F3 107.0(3) . . ?
F1 C8 C7 114.1(3) . . ?
F2 C8 F3 105.5(3) . . ?
F2 C8 C7 111.8(3) . . ?
F3 C8 C7 111.1(3) . . ?
N2 C9 H9A 109.8 . . ?
N2 C9 H9B 109.8 . . ?
N2 C9 C10 109.2(3) . . ?
H9A C9 H9B 108.3 . . ?
C10 C9 H9A 109.8 . . ?
C10 C9 H9B 109.8 . . ?
O1 C10 C9 112.4(3) . . ?
O1 C10 H10A 109.1 . . ?
O1 C10 H10B 109.1 . . ?
C9 C10 H10A 109.1 . . ?
C9 C10 H10B 109.1 . . ?
H10A C10 H10B 107.9 . . ?
O1 C11 H11A 109.4 . . ?
O1 C11 H11B 109.4 . . ?
O1 C11 C12 111.1(3) . . ?
H11A C11 H11B 108.0 . . ?
C12 C11 H11A 109.4 . . ?
C12 C11 H11B 109.4 . . ?
N2 C12 C11 109.9(3) . . ?
N2 C12 H12A 109.7 . . ?
N2 C12 H12B 109.7 . . ?
C11 C12 H12A 109.7 . . ?
C11 C12 H12B 109.7 . . ?
H12A C12 H12B 108.2 . . ?

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 C2 C3 C4 -178.8(3) . . . . ?
Br2 C4 C5 C6 -178.8(3) . . . . ?
O1 C11 C12 N2 57.1(5) . . . . ?
N1 N2 C9 C10 -165.8(4) . . . . ?
N1 N2 C12 C11 159.4(3) . . . . ?
N1 C7 C8 F1 7.5(5) . . . . ?
N1 C7 C8 F2 128.8(4) . . . . ?
N1 C7 C8 F3 -113.6(4) . . . . ?
N2 N1 C7 C6 -2.3(7) . . . . ?
N2 N1 C7 C8 174.3(3) . . . . ?
N2 C9 C10 O1 -55.7(5) . . . . ?
C1 C2 C3 C4 0.0(5) . . . . ?
C1 C6 C7 N1 -91.3(5) . . . . ?
C1 C6 C7 C8 92.1(4) . . . . ?
C2 C1 C6 C5 -2.7(5) . . . . ?
C2 C1 C6 C7 179.9(3) . . . . ?
C2 C3 C4 Br2 178.0(3) . . . . ?
C2 C3 C4 C5 -1.3(5) . . . . ?
C3 C4 C5 C6 0.6(5) . . . . ?
C4 C5 C6 C1 1.5(5) . . . . ?
C4 C5 C6 C7 178.9(3) . . . . ?
C5 C6 C7 N1 91.3(5) . . . . ?
C5 C6 C7 C8 -85.4(4) . . . . ?
C6 C1 C2 Br1 -179.2(2) . . . . ?
C6 C1 C2 C3 1.9(5) . . . . ?
C6 C7 C8 F1 -175.2(3) . . . . ?
C6 C7 C8 F2 -53.9(4) . . . . ?
C6 C7 C8 F3 63.7(4) . . . . ?
C7 N1 N2 C9 24.2(6) . . . . ?
C7 N1 N2 C12 166.9(4) . . . . ?
C9 N2 C12 C11 -53.0(4) . . . . ?
C10 O1 C11 C12 -60.9(4) . . . . ?
C11 O1 C10 C9 60.6(5) . . . . ?
C12 N2 C9 C10 51.6(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
