# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_mo_220822peng_0ma
_database_code_depnum_ccdc_archive 'CCDC 2234192'
loop_
_audit_author_name
_audit_author_address
'Andrei Astachkine'
;University of Arizona
United States of America
;
_audit_update_record             
;
2023-01-04 deposited with the CCDC.	2023-02-28 downloaded from the CCDC.
;
_audit_creation_date             2022-08-23
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C8 H9 Br N2 O2'
_chemical_formula_sum            'C8 H9 Br N2 O2'
_chemical_formula_weight         245.08
_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      orthorhombic
_space_group_IT_number           56
_space_group_name_H-M_alt        'P c c n'
_space_group_name_Hall           '-P 2ab 2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-x, y+1/2, -z+1/2'
'x+1/2, -y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'x, -y-1/2, z-1/2'
'-x-1/2, y, z-1/2'

_cell_length_a                   13.2630(13)
_cell_length_b                   24.954(2)
_cell_length_c                   5.6399(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1866.6(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6364
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.38
_cell_measurement_theta_min      2.89
_shelx_estimated_absorpt_T_max   0.811
_shelx_estimated_absorpt_T_min   0.274
_exptl_absorpt_coefficient_mu    4.372
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5007
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1059 before and 0.0293 after correction.
The Ratio of minimum to maximum transmission is 0.6717.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.744
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0190
_diffrn_reflns_av_unetI/netI     0.0128
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            11450
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.383
_diffrn_reflns_theta_min         1.632
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_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                1743
_reflns_number_total             1899
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.424
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         1899
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0213
_refine_ls_R_factor_gt           0.0185
_refine_ls_restrained_S_all      1.042
_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)+(0.0244P)²+1.3127P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0462
_refine_ls_wR_factor_ref         0.0473
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C3(H3B,H3A)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C5(H5), C8(H8)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_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 0.35984(2) 0.70010(2) -0.11847(3) 0.01781(7) Uani 1 1 d . . . . .
O1 O 0.38383(9) 0.32447(5) 0.5371(2) 0.0186(2) Uani 1 1 d . . . . .
O2 O 0.34373(8) 0.40060(5) 0.7275(2) 0.0197(3) Uani 1 1 d . . . . .
N1 N 0.37078(9) 0.55118(6) 0.1510(2) 0.0144(3) Uani 1 1 d . . . . .
N2 N 0.38917(10) 0.57828(6) 0.3556(2) 0.0163(3) Uani 1 1 d . . . . .
C4 C 0.39531(11) 0.46430(6) 0.3285(3) 0.0153(3) Uani 1 1 d . . . . .
H4 H 0.412315 0.481467 0.473385 0.018 Uiso 1 1 calc R U . . .
C3 C 0.39858(12) 0.40419(6) 0.3180(3) 0.0157(3) Uani 1 1 d . . . . .
H3B H 0.467279 0.392727 0.271742 0.019 Uiso 1 1 calc R U . . .
H3A H 0.351287 0.391629 0.194122 0.019 Uiso 1 1 calc R U . . .
C6 C 0.35769(11) 0.58440(7) -0.0372(3) 0.0144(3) Uani 1 1 d . . . . .
H6 H 0.344066 0.574399 -0.196536 0.017 Uiso 1 1 calc R U . . .
C7 C 0.36823(11) 0.63539(6) 0.0503(3) 0.0143(3) Uani 1 1 d . . . . .
C5 C 0.36996(11) 0.49425(7) 0.1461(3) 0.0156(3) Uani 1 1 d . . . . .
H5 H 0.350064 0.476914 0.003601 0.019 Uiso 1 1 calc R U . . .
C2 C 0.37129(11) 0.37815(7) 0.5508(3) 0.0144(3) Uani 1 1 d . . . . .
C8 C 0.38721(12) 0.62978(7) 0.2930(3) 0.0163(3) Uani 1 1 d . . . . .
H8 H 0.397365 0.658830 0.399250 0.020 Uiso 1 1 calc R U . . .
C1 C 0.36878(13) 0.29621(7) 0.7582(3) 0.0233(4) Uani 1 1 d . . . . .
H1A H 0.382810 0.258013 0.735071 0.035 Uiso 1 1 calc R U . . .
H1B H 0.298851 0.300798 0.810537 0.035 Uiso 1 1 calc R U . . .
H1C H 0.414483 0.310683 0.878803 0.035 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 C7 1.8778(16) . ?
O1 C2 1.3519(19) . ?
O1 C1 1.446(2) . ?
O2 C2 1.200(2) . ?
N1 N2 1.3597(18) . ?
N1 C6 1.358(2) . ?
N1 C5 1.421(2) . ?
N2 C8 1.333(2) . ?
C4 H4 0.9500 . ?
C4 C3 1.502(2) . ?
C4 C5 1.315(2) . ?
C3 H3B 0.9900 . ?
C3 H3A 0.9900 . ?
C3 C2 1.509(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.372(2) . ?
C7 C8 1.399(2) . ?
C5 H5 0.9500 . ?
C8 H8 0.9500 . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 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
C2 O1 C1 114.65(13) . . ?
N2 N1 C5 121.00(13) . . ?
C6 N1 N2 112.50(13) . . ?
C6 N1 C5 126.46(14) . . ?
C8 N2 N1 104.56(13) . . ?
C3 C4 H4 118.5 . . ?
C5 C4 H4 118.5 . . ?
C5 C4 C3 122.98(15) . . ?
C4 C3 H3B 109.0 . . ?
C4 C3 H3A 109.0 . . ?
C4 C3 C2 112.90(14) . . ?
H3B C3 H3A 107.8 . . ?
C2 C3 H3B 109.0 . . ?
C2 C3 H3A 109.0 . . ?
N1 C6 H6 127.1 . . ?
N1 C6 C7 105.79(14) . . ?
C7 C6 H6 127.1 . . ?
C6 C7 Br1 127.53(13) . . ?
C6 C7 C8 106.11(15) . . ?
C8 C7 Br1 126.36(13) . . ?
N1 C5 H5 118.3 . . ?
C4 C5 N1 123.44(15) . . ?
C4 C5 H5 118.3 . . ?
O1 C2 C3 110.35(14) . . ?
O2 C2 O1 123.17(16) . . ?
O2 C2 C3 126.47(15) . . ?
N2 C8 C7 111.05(15) . . ?
N2 C8 H8 124.5 . . ?
C7 C8 H8 124.5 . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 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
Br1 C7 C8 N2 -179.38(11) . . . . ?
N1 N2 C8 C7 -0.30(18) . . . . ?
N1 C6 C7 Br1 179.49(10) . . . . ?
N1 C6 C7 C8 -0.21(16) . . . . ?
N2 N1 C6 C7 0.04(17) . . . . ?
N2 N1 C5 C4 -6.3(2) . . . . ?
C4 C3 C2 O1 -174.75(12) . . . . ?
C4 C3 C2 O2 4.1(2) . . . . ?
C3 C4 C5 N1 -177.21(14) . . . . ?
C6 N1 N2 C8 0.16(17) . . . . ?
C6 N1 C5 C4 171.33(15) . . . . ?
C6 C7 C8 N2 0.33(18) . . . . ?
C5 N1 N2 C8 178.12(13) . . . . ?
C5 N1 C6 C7 -177.78(13) . . . . ?
C5 C4 C3 C2 -147.55(15) . . . . ?
C1 O1 C2 O2 -4.5(2) . . . . ?
C1 O1 C2 C3 174.43(12) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
