# 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_xuj008
_database_code_depnum_ccdc_archive 'CCDC 2100120'
loop_
_audit_author_name
_audit_author_address
'Yuqiao Zhou'
;College of Chemistry, Sichuan University, Chengdu, China
China
;
_audit_update_record             
;
2021-07-29 deposited with the CCDC.	2021-12-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H16 Br N O3'
_chemical_formula_sum            'C14 H16 Br N O3'
_chemical_formula_weight         326.19

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'
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'
Br Br -0.2901 2.4595 '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                   9.8997(3)
_cell_length_b                   10.1961(3)
_cell_length_c                   14.3871(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1452.21(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    8664
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      27.50

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.492
_exptl_crystal_F_000             664
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.328
_exptl_crystal_size_mid          0.272
_exptl_crystal_size_min          0.262
_exptl_absorpt_coefficient_mu    2.834
_shelx_estimated_absorpt_T_min   0.457
_shelx_estimated_absorpt_T_max   0.524
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.4385
_exptl_absorpt_correction_T_max  0.6424
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture Photon II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10060
_diffrn_reflns_av_unetI/netI     0.0365
_diffrn_reflns_av_R_equivalents  0.0184
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.448
_diffrn_reflns_theta_max         27.521
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measured_fraction_theta_full 0.968
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_Laue_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_point_group_measured_fraction_full 0.941
_reflns_number_total             3175
_reflns_number_gt                3048
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.701
_reflns_Friedel_fraction_max     0.916
_reflns_Friedel_fraction_full    0.904

_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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+0.1558P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1213 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.031(3)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3175
_refine_ls_number_parameters     183
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0199
_refine_ls_R_factor_gt           0.0188
_refine_ls_wR_factor_ref         0.0484
_refine_ls_wR_factor_gt          0.0479
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_refine_ls_shift/su_max          0.001
_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 0.39883(3) 0.14928(2) 0.41095(2) 0.03859(9) Uani 1 1 d . . . . .
O1 O 0.18986(15) 0.84842(15) 0.50511(11) 0.0262(3) Uani 1 1 d D . . . .
H1O H 0.137(3) 0.811(3) 0.4699(19) 0.048(9) Uiso 1 1 d D . . . .
O2 O 0.42667(15) 0.83258(13) 0.37980(10) 0.0271(3) Uani 1 1 d . . . . .
O3 O 0.51239(14) 0.78693(14) 0.60211(11) 0.0251(3) Uani 1 1 d . . . . .
N1 N 0.34941(17) 0.93979(17) 0.62901(12) 0.0221(4) Uani 1 1 d D . . . .
H1N H 0.267(2) 0.960(2) 0.6092(17) 0.022(6) Uiso 1 1 d D . . . .
C1 C 0.3031(2) 0.76654(19) 0.51942(14) 0.0203(4) Uani 1 1 d . . . . .
C2 C 0.3810(2) 0.74471(19) 0.42736(13) 0.0213(4) Uani 1 1 d . . . . .
C3 C 0.3887(2) 0.60296(18) 0.41001(14) 0.0202(4) Uani 1 1 d . . . . .
C4 C 0.4457(2) 0.5377(2) 0.33500(15) 0.0270(5) Uani 1 1 d . . . . .
H4 H 0.483870 0.585353 0.284685 0.032 Uiso 1 1 calc R U . . .
C5 C 0.4459(2) 0.4019(2) 0.33488(16) 0.0292(5) Uani 1 1 d . . . . .
H5 H 0.482181 0.354808 0.283653 0.035 Uiso 1 1 calc R U . . .
C6 C 0.3924(2) 0.33548(18) 0.41084(14) 0.0263(4) Uani 1 1 d . . . . .
C7 C 0.3331(2) 0.3991(2) 0.48557(15) 0.0244(4) Uani 1 1 d . . . . .
H7 H 0.295656 0.351461 0.536117 0.029 Uiso 1 1 calc R U . . .
C8 C 0.33068(19) 0.5357(2) 0.48365(14) 0.0199(4) Uani 1 1 d . . . . .
C9 C 0.2682(2) 0.62640(19) 0.55455(14) 0.0227(4) Uani 1 1 d . . . . .
H9A H 0.307136 0.610856 0.616973 0.027 Uiso 1 1 calc R U . . .
H9B H 0.169180 0.613638 0.557643 0.027 Uiso 1 1 calc R U . . .
C11 C 0.3987(2) 0.83425(17) 0.58806(13) 0.0200(3) Uani 1 1 d . . . . .
C12 C 0.4160(2) 1.02381(19) 0.70001(13) 0.0215(4) Uani 1 1 d . . . . .
C13 C 0.5468(2) 1.0803(2) 0.66186(18) 0.0309(5) Uani 1 1 d . . . . .
H13A H 0.607315 1.008654 0.643927 0.046 Uiso 1 1 calc R U . . .
H13B H 0.590288 1.134146 0.709701 0.046 Uiso 1 1 calc R U . . .
H13C H 0.526977 1.134699 0.607353 0.046 Uiso 1 1 calc R U . . .
C14 C 0.4435(3) 0.9448(2) 0.78767(16) 0.0329(5) Uani 1 1 d . . . . .
H14A H 0.513120 0.878980 0.774907 0.049 Uiso 1 1 calc R U . . .
H14B H 0.360249 0.900975 0.807542 0.049 Uiso 1 1 calc R U . . .
H14C H 0.474699 1.003709 0.837038 0.049 Uiso 1 1 calc R U . . .
C15 C 0.3140(2) 1.1320(2) 0.72092(17) 0.0318(5) Uani 1 1 d . . . . .
H15A H 0.231019 1.092981 0.745723 0.048 Uiso 1 1 calc R U . . .
H15B H 0.293301 1.179933 0.663632 0.048 Uiso 1 1 calc R U . . .
H15C H 0.352174 1.192528 0.766842 0.048 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 C6 1.8995(18) . ?
O1 C1 1.413(2) . ?
O1 H1O 0.82(2) . ?
O2 C2 1.215(2) . ?
O3 C11 1.241(2) . ?
N1 C11 1.320(2) . ?
N1 C12 1.487(3) . ?
N1 H1N 0.887(19) . ?
C1 C11 1.532(3) . ?
C1 C2 1.548(3) . ?
C1 C9 1.555(3) . ?
C2 C3 1.469(3) . ?
C3 C8 1.387(3) . ?
C3 C4 1.388(3) . ?
C4 C5 1.385(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.391(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.386(3) . ?
C7 C8 1.393(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.509(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C12 C13 1.520(3) . ?
C12 C14 1.521(3) . ?
C12 C15 1.525(3) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?

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
C1 O1 H1O 109(2) . . ?
C11 N1 C12 127.77(17) . . ?
C11 N1 H1N 112.6(16) . . ?
C12 N1 H1N 119.6(16) . . ?
O1 C1 C11 108.52(15) . . ?
O1 C1 C2 110.80(16) . . ?
C11 C1 C2 107.99(16) . . ?
O1 C1 C9 114.46(17) . . ?
C11 C1 C9 110.00(16) . . ?
C2 C1 C9 104.87(15) . . ?
O2 C2 C3 127.65(19) . . ?
O2 C2 C1 124.14(17) . . ?
C3 C2 C1 108.22(17) . . ?
C8 C3 C4 121.71(18) . . ?
C8 C3 C2 109.60(17) . . ?
C4 C3 C2 128.68(19) . . ?
C5 C4 C3 118.7(2) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C4 C5 C6 119.0(2) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 H5 120.5 . . ?
C7 C6 C5 122.88(19) . . ?
C7 C6 Br1 118.78(16) . . ?
C5 C6 Br1 118.33(15) . . ?
C6 C7 C8 117.4(2) . . ?
C6 C7 H7 121.3 . . ?
C8 C7 H7 121.3 . . ?
C3 C8 C7 120.16(18) . . ?
C3 C8 C9 112.52(17) . . ?
C7 C8 C9 127.31(19) . . ?
C8 C9 C1 104.62(16) . . ?
C8 C9 H9A 110.8 . . ?
C1 C9 H9A 110.8 . . ?
C8 C9 H9B 110.8 . . ?
C1 C9 H9B 110.8 . . ?
H9A C9 H9B 108.9 . . ?
O3 C11 N1 125.39(18) . . ?
O3 C11 C1 119.33(16) . . ?
N1 C11 C1 115.28(17) . . ?
N1 C12 C13 110.36(16) . . ?
N1 C12 C14 110.11(17) . . ?
C13 C12 C14 110.36(19) . . ?
N1 C12 C15 105.00(16) . . ?
C13 C12 C15 111.15(18) . . ?
C14 C12 C15 109.73(18) . . ?
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 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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
O1 C1 C2 O2 57.0(2) . . . . ?
C11 C1 C2 O2 -61.7(2) . . . . ?
C9 C1 C2 O2 -179.02(18) . . . . ?
O1 C1 C2 C3 -123.25(17) . . . . ?
C11 C1 C2 C3 118.02(17) . . . . ?
C9 C1 C2 C3 0.7(2) . . . . ?
O2 C2 C3 C8 176.56(19) . . . . ?
C1 C2 C3 C8 -3.2(2) . . . . ?
O2 C2 C3 C4 -2.0(4) . . . . ?
C1 C2 C3 C4 178.2(2) . . . . ?
C8 C3 C4 C5 -0.9(3) . . . . ?
C2 C3 C4 C5 177.5(2) . . . . ?
C3 C4 C5 C6 -1.7(3) . . . . ?
C4 C5 C6 C7 2.8(3) . . . . ?
C4 C5 C6 Br1 -178.07(18) . . . . ?
C5 C6 C7 C8 -1.2(3) . . . . ?
Br1 C6 C7 C8 179.64(15) . . . . ?
C4 C3 C8 C7 2.5(3) . . . . ?
C2 C3 C8 C7 -176.21(18) . . . . ?
C4 C3 C8 C9 -176.77(19) . . . . ?
C2 C3 C8 C9 4.5(2) . . . . ?
C6 C7 C8 C3 -1.4(3) . . . . ?
C6 C7 C8 C9 177.8(2) . . . . ?
C3 C8 C9 C1 -3.9(2) . . . . ?
C7 C8 C9 C1 176.9(2) . . . . ?
O1 C1 C9 C8 123.34(18) . . . . ?
C11 C1 C9 C8 -114.19(18) . . . . ?
C2 C1 C9 C8 1.7(2) . . . . ?
C12 N1 C11 O3 -0.5(3) . . . . ?
C12 N1 C11 C1 178.37(18) . . . . ?
O1 C1 C11 O3 -171.41(17) . . . . ?
C2 C1 C11 O3 -51.2(2) . . . . ?
C9 C1 C11 O3 62.7(2) . . . . ?
O1 C1 C11 N1 9.7(2) . . . . ?
C2 C1 C11 N1 129.83(18) . . . . ?
C9 C1 C11 N1 -116.26(19) . . . . ?
C11 N1 C12 C13 59.2(3) . . . . ?
C11 N1 C12 C14 -62.9(3) . . . . ?
C11 N1 C12 C15 179.0(2) . . . . ?

_refine_diff_density_max         0.356
_refine_diff_density_min         -0.390
_refine_diff_density_rms         0.036


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: DCM, PE'
