# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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. 
# 
#######################################################################

data_mo_d8v191167_0m
_database_code_depnum_ccdc_archive 'CCDC 2184389'
loop_
_audit_author_name
_audit_author_address
'Xuebing Leng'
;Shanghai Institute of Organic Chemistry
China
;
_audit_update_record             
;
2022-07-06 deposited with the CCDC.	2022-08-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H12 Br N O2'
_chemical_formula_weight         294.15

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   9.3599(9)
_cell_length_b                   11.1041(9)
_cell_length_c                   11.8507(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1231.68(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1877
_cell_measurement_theta_min      5.027
_cell_measurement_theta_max      49.582

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.586
_exptl_crystal_F_000             592
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    3.326
_shelx_estimated_absorpt_T_min   0.586
_shelx_estimated_absorpt_T_max   0.711
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4528
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5815
_diffrn_reflns_av_unetI/netI     0.0560
_diffrn_reflns_av_R_equivalents  0.0410
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.514
_diffrn_reflns_theta_max         25.470
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2290
_reflns_number_gt                1624
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.715
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.999

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0498P)²+0.5678P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 548 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.467(9)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         2290
_refine_ls_number_parameters     156
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0727
_refine_ls_R_factor_gt           0.0451
_refine_ls_wR_factor_ref         0.1135
_refine_ls_wR_factor_gt          0.1023
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.46208(11) 0.88329(6) 0.43464(8) 0.0747(4) Uani 1 1 d . . . . .
O1 O 0.3928(7) 0.3200(5) 0.6911(4) 0.0627(16) Uani 1 1 d . . . . .
O2 O 0.4631(7) 0.1597(4) 0.3760(4) 0.0597(14) Uani 1 1 d . . . . .
N1 N 0.3620(6) 0.3504(5) 0.5047(4) 0.0411(14) Uani 1 1 d . . . . .
C1 C 0.3979(8) 0.4753(6) 0.5030(6) 0.0398(16) Uani 1 1 d . . . . .
C2 C 0.4651(9) 0.5441(6) 0.5829(6) 0.0500(18) Uani 1 1 d . . . . .
H2 H 0.4961 0.5096 0.6501 0.060 Uiso 1 1 calc R U . . .
C3 C 0.4864(8) 0.6661(6) 0.5625(7) 0.0542(19) Uani 1 1 d . . . . .
H3 H 0.5331 0.7138 0.6154 0.065 Uiso 1 1 calc R U . . .
C4 C 0.4373(8) 0.7158(6) 0.4624(6) 0.050(2) Uani 1 1 d . . . . .
C5 C 0.3688(8) 0.6489(6) 0.3823(6) 0.0454(18) Uani 1 1 d . . . . .
H5 H 0.3364 0.6839 0.3158 0.055 Uiso 1 1 calc R U . . .
C6 C 0.3490(8) 0.5268(6) 0.4030(5) 0.0390(16) Uani 1 1 d . . . . .
C7 C 0.2811(8) 0.4353(6) 0.3302(6) 0.0431(17) Uani 1 1 d . . . . .
H7 H 0.2996 0.4359 0.2488 0.052 Uiso 1 1 calc R U . . .
C8 C 0.1530(8) 0.3714(7) 0.3748(6) 0.0491(18) Uani 1 1 d . . . . .
H8A H 0.0918 0.3308 0.3208 0.059 Uiso 1 1 calc R U . . .
H8B H 0.1032 0.4076 0.4380 0.059 Uiso 1 1 calc R U . . .
C9 C 0.2977(8) 0.3177(6) 0.3969(6) 0.0422(18) Uani 1 1 d . . . . .
C10 C 0.3572(9) 0.2084(6) 0.3405(6) 0.0471(18) Uani 1 1 d . . . . .
C11 C 0.2796(10) 0.1623(8) 0.2374(6) 0.064(2) Uani 1 1 d . . . . .
H11A H 0.2821 0.2224 0.1792 0.097 Uiso 1 1 calc R U . . .
H11B H 0.1821 0.1450 0.2566 0.097 Uiso 1 1 calc R U . . .
H11C H 0.3251 0.0902 0.2108 0.097 Uiso 1 1 calc R U . . .
C12 C 0.3454(9) 0.2851(6) 0.6021(6) 0.0480(19) Uani 1 1 d . . . . .
C13 C 0.2624(9) 0.1697(7) 0.5922(7) 0.062(2) Uani 1 1 d . . . . .
H13A H 0.3215 0.1090 0.5581 0.093 Uiso 1 1 calc R U . . .
H13B H 0.1794 0.1828 0.5462 0.093 Uiso 1 1 calc R U . . .
H13C H 0.2334 0.1435 0.6659 0.093 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 C4 1.902(6) . ?
O1 C12 1.208(9) . ?
O2 C10 1.204(9) . ?
N1 C12 1.372(8) . ?
N1 C1 1.426(9) . ?
N1 C9 1.458(8) . ?
C1 C2 1.370(10) . ?
C1 C6 1.394(10) . ?
C2 C3 1.390(10) . ?
C2 H2 0.9300 . ?
C3 C4 1.388(10) . ?
C3 H3 0.9300 . ?
C4 C5 1.365(9) . ?
C5 C6 1.390(9) . ?
C5 H5 0.9300 . ?
C6 C7 1.476(9) . ?
C7 C8 1.490(10) . ?
C7 C9 1.535(9) . ?
C7 H7 0.9800 . ?
C8 C9 1.503(10) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.494(10) . ?
C10 C11 1.511(10) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.503(11) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?

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 N1 C1 123.5(6) . . ?
C12 N1 C9 123.9(6) . . ?
C1 N1 C9 109.1(5) . . ?
C2 C1 C6 120.6(6) . . ?
C2 C1 N1 129.9(7) . . ?
C6 C1 N1 109.5(6) . . ?
C1 C2 C3 119.3(7) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
C4 C3 C2 119.3(7) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C5 C4 C3 122.2(6) . . ?
C5 C4 Br1 118.0(6) . . ?
C3 C4 Br1 119.8(5) . . ?
C4 C5 C6 118.1(7) . . ?
C4 C5 H5 120.9 . . ?
C6 C5 H5 120.9 . . ?
C5 C6 C1 120.4(6) . . ?
C5 C6 C7 128.7(6) . . ?
C1 C6 C7 110.8(6) . . ?
C6 C7 C8 117.8(6) . . ?
C6 C7 C9 104.0(6) . . ?
C8 C7 C9 59.6(5) . . ?
C6 C7 H7 119.6 . . ?
C8 C7 H7 119.6 . . ?
C9 C7 H7 119.6 . . ?
C7 C8 C9 61.7(4) . . ?
C7 C8 H8A 117.6 . . ?
C9 C8 H8A 117.6 . . ?
C7 C8 H8B 117.6 . . ?
C9 C8 H8B 117.6 . . ?
H8A C8 H8B 114.7 . . ?
N1 C9 C10 116.2(7) . . ?
N1 C9 C8 115.2(6) . . ?
C10 C9 C8 125.5(7) . . ?
N1 C9 C7 106.3(5) . . ?
C10 C9 C7 119.9(6) . . ?
C8 C9 C7 58.7(5) . . ?
O2 C10 C9 121.0(7) . . ?
O2 C10 C11 121.8(7) . . ?
C9 C10 C11 117.2(7) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O1 C12 N1 121.5(7) . . ?
O1 C12 C13 122.1(7) . . ?
N1 C12 C13 116.3(7) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 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
C12 N1 C1 C2 23.2(12) . . . . ?
C9 N1 C1 C2 -177.0(8) . . . . ?
C12 N1 C1 C6 -154.8(7) . . . . ?
C9 N1 C1 C6 5.0(8) . . . . ?
C6 C1 C2 C3 -1.1(12) . . . . ?
N1 C1 C2 C3 -178.9(7) . . . . ?
C1 C2 C3 C4 0.9(12) . . . . ?
C2 C3 C4 C5 -0.3(12) . . . . ?
C2 C3 C4 Br1 178.7(6) . . . . ?
C3 C4 C5 C6 -0.2(12) . . . . ?
Br1 C4 C5 C6 -179.2(6) . . . . ?
C4 C5 C6 C1 0.1(11) . . . . ?
C4 C5 C6 C7 -179.0(7) . . . . ?
C2 C1 C6 C5 0.6(12) . . . . ?
N1 C1 C6 C5 178.8(7) . . . . ?
C2 C1 C6 C7 179.8(7) . . . . ?
N1 C1 C6 C7 -2.0(8) . . . . ?
C5 C6 C7 C8 -119.8(8) . . . . ?
C1 C6 C7 C8 61.1(9) . . . . ?
C5 C6 C7 C9 177.6(8) . . . . ?
C1 C6 C7 C9 -1.6(8) . . . . ?
C6 C7 C8 C9 -90.3(7) . . . . ?
C12 N1 C9 C10 -69.8(9) . . . . ?
C1 N1 C9 C10 130.5(7) . . . . ?
C12 N1 C9 C8 91.3(8) . . . . ?
C1 N1 C9 C8 -68.4(7) . . . . ?
C12 N1 C9 C7 153.9(6) . . . . ?
C1 N1 C9 C7 -5.8(8) . . . . ?
C7 C8 C9 N1 94.4(6) . . . . ?
C7 C8 C9 C10 -106.5(7) . . . . ?
C6 C7 C9 N1 4.4(8) . . . . ?
C8 C7 C9 N1 -109.9(7) . . . . ?
C6 C7 C9 C10 -129.9(7) . . . . ?
C8 C7 C9 C10 115.7(8) . . . . ?
C6 C7 C9 C8 114.3(7) . . . . ?
N1 C9 C10 O2 -8.6(10) . . . . ?
C8 C9 C10 O2 -167.5(7) . . . . ?
C7 C9 C10 O2 121.5(8) . . . . ?
N1 C9 C10 C11 171.7(6) . . . . ?
C8 C9 C10 C11 12.8(10) . . . . ?
C7 C9 C10 C11 -58.3(10) . . . . ?
C1 N1 C12 O1 -18.2(11) . . . . ?
C9 N1 C12 O1 -175.0(7) . . . . ?
C1 N1 C12 C13 160.5(7) . . . . ?
C9 N1 C12 C13 3.7(10) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C2 H2 O1 0.93 2.37 2.880(9) 114.5 .
C5 H5 O1 0.93 2.61 3.355(9) 138.0 2_564
C8 H8A O1 0.97 2.51 3.325(9) 141.8 4_456
C8 H8B Br1 0.97 3.07 3.964(8) 154.3 4_466
C13 H13A O2 0.96 2.59 3.178(10) 119.5 .

_refine_diff_density_max         0.357
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.050

_shelxl_version_number           2013-4

