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

data_20211208hl_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2235710'
loop_
_audit_author_name
_audit_author_address
WANGWEIJUN
;Northwest University
China
;
_audit_update_record             
;
2023-01-12 deposited with the CCDC.	2023-06-26 downloaded from the CCDC.
;
_audit_creation_date             2022-11-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        (Z)-1-(1,2-dibromovinyl)-4-nitrobenzene
_chemical_formula_moiety         'C8 H5 Br2 N O2'
_chemical_formula_sum            'C8 H5 Br2 N O2'
_chemical_formula_weight         306.95
_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 0.0137 0.0067 '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 -0.9338 1.0006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 '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                   8.4516(5)
_cell_length_b                   12.1323(7)
_cell_length_c                   9.7322(6)
_cell_angle_alpha                90
_cell_angle_beta                 110.762(2)
_cell_angle_gamma                90
_cell_volume                     933.11(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4088
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      54.81
_cell_measurement_theta_min      4.87
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    7.132
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.5497
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0988 before and 0.0583 after correction.
The Ratio of minimum to maximum transmission is 0.7322.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.185
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    none
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.23
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0459
_diffrn_reflns_av_unetI/netI     0.0350
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            8511
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.928
_diffrn_reflns_theta_min         4.868
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_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           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1486
_reflns_number_total             1774
_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 (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.823
_refine_diff_density_min         -1.023
_refine_diff_density_rms         0.142
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         1774
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0466
_refine_ls_R_factor_gt           0.0368
_refine_ls_restrained_S_all      1.065
_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)+(0.0513P)²+1.6961P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0898
_refine_ls_wR_factor_ref         0.0958
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C2(H2), C5(H5), C8(H8)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
Br2 Br 0.00529(6) 0.69859(4) 0.06330(5) 0.02707(18) Uani 1 1 d . . . . .
Br1 Br -0.25100(7) 0.50145(4) 0.12450(5) 0.02917(18) Uani 1 1 d . . . . .
O1 O -0.4352(4) 1.2158(3) 0.1994(4) 0.0285(7) Uani 1 1 d . . . . .
N1 N -0.3578(5) 1.1877(3) 0.1195(4) 0.0228(8) Uani 1 1 d . . . . .
C3 C -0.1929(5) 0.9273(3) 0.0187(5) 0.0201(9) Uani 1 1 d . . . . .
H3 H -0.1382 0.9031 -0.0460 0.024 Uiso 1 1 calc R . . . .
C6 C -0.3530(6) 0.9981(4) 0.2092(5) 0.0226(9) Uani 1 1 d . . . . .
H6 H -0.4085 1.0231 0.2729 0.027 Uiso 1 1 calc R . . . .
O2 O -0.3163(4) 1.2519(3) 0.0410(4) 0.0304(8) Uani 1 1 d . . . . .
C2 C -0.2352(5) 1.0375(4) 0.0208(5) 0.0200(9) Uani 1 1 d . . . . .
H2 H -0.2101 1.0893 -0.0419 0.024 Uiso 1 1 calc R . . . .
C5 C -0.3088(5) 0.8882(4) 0.2076(5) 0.0216(9) Uani 1 1 d . . . . .
H5 H -0.3320 0.8375 0.2723 0.026 Uiso 1 1 calc R . . . .
C7 C -0.1910(5) 0.7329(4) 0.1071(5) 0.0207(9) Uani 1 1 d . . . . .
C4 C -0.2303(5) 0.8516(4) 0.1114(5) 0.0198(9) Uani 1 1 d . . . . .
C1 C -0.3147(5) 1.0706(3) 0.1159(5) 0.0209(9) Uani 1 1 d . . . . .
C8 C -0.2889(6) 0.6533(4) 0.1284(5) 0.0252(10) Uani 1 1 d . . . . .
H8 H -0.3870 0.6758 0.1472 0.030 Uiso 1 1 calc R . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br2 0.0225(3) 0.0271(3) 0.0340(3) 0.0008(2) 0.0130(2) 0.00468(19)
Br1 0.0440(3) 0.0186(3) 0.0292(3) 0.00139(19) 0.0182(2) 0.0028(2)
O1 0.0331(18) 0.0270(18) 0.0314(18) -0.0012(14) 0.0187(15) 0.0064(14)
N1 0.0220(19) 0.023(2) 0.025(2) -0.0030(16) 0.0099(16) -0.0020(15)
C3 0.023(2) 0.020(2) 0.020(2) -0.0005(17) 0.0103(18) -0.0004(17)
C6 0.022(2) 0.026(2) 0.021(2) -0.0017(18) 0.0079(18) 0.0006(18)
O2 0.0395(19) 0.0216(17) 0.038(2) 0.0042(15) 0.0238(16) 0.0029(15)
C2 0.020(2) 0.019(2) 0.022(2) -0.0012(18) 0.0092(18) -0.0044(18)
C5 0.023(2) 0.024(2) 0.020(2) 0.0022(18) 0.0107(18) -0.0046(19)
C7 0.021(2) 0.024(2) 0.020(2) -0.0015(17) 0.0096(17) 0.0005(18)
C4 0.018(2) 0.018(2) 0.021(2) -0.0006(17) 0.0044(18) -0.0012(17)
C1 0.021(2) 0.019(2) 0.019(2) -0.0023(17) 0.0033(17) 0.0011(18)
C8 0.031(2) 0.021(2) 0.028(3) 0.0010(19) 0.015(2) 0.004(2)

_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
Br2 C7 1.899(4) . ?
Br1 C8 1.873(4) . ?
O1 N1 1.229(5) . ?
N1 O2 1.226(5) . ?
N1 C1 1.471(5) . ?
C3 C2 1.386(6) . ?
C3 C4 1.400(6) . ?
C6 C5 1.386(6) . ?
C6 C1 1.382(6) . ?
C2 C1 1.382(6) . ?
C5 C4 1.398(6) . ?
C7 C4 1.481(6) . ?
C7 C8 1.335(6) . ?

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
O1 N1 C1 118.4(4) . . ?
O2 N1 O1 123.5(4) . . ?
O2 N1 C1 118.1(4) . . ?
C2 C3 C4 120.3(4) . . ?
C1 C6 C5 118.5(4) . . ?
C1 C2 C3 118.6(4) . . ?
C6 C5 C4 120.5(4) . . ?
C4 C7 Br2 116.2(3) . . ?
C8 C7 Br2 121.0(3) . . ?
C8 C7 C4 122.7(4) . . ?
C3 C4 C7 121.0(4) . . ?
C5 C4 C3 119.5(4) . . ?
C5 C4 C7 119.5(4) . . ?
C6 C1 N1 118.8(4) . . ?
C6 C1 C2 122.6(4) . . ?
C2 C1 N1 118.6(4) . . ?
C7 C8 Br1 126.0(4) . . ?

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
Br2 C7 C4 C3 33.2(5) . . . . ?
Br2 C7 C4 C5 -148.0(3) . . . . ?
Br2 C7 C8 Br1 1.7(6) . . . . ?
O1 N1 C1 C6 -4.1(6) . . . . ?
O1 N1 C1 C2 176.8(4) . . . . ?
C3 C2 C1 N1 179.3(4) . . . . ?
C3 C2 C1 C6 0.2(6) . . . . ?
C6 C5 C4 C3 1.5(6) . . . . ?
C6 C5 C4 C7 -177.3(4) . . . . ?
O2 N1 C1 C6 176.8(4) . . . . ?
O2 N1 C1 C2 -2.3(6) . . . . ?
C2 C3 C4 C5 -0.8(6) . . . . ?
C2 C3 C4 C7 178.0(4) . . . . ?
C5 C6 C1 N1 -178.6(4) . . . . ?
C5 C6 C1 C2 0.4(7) . . . . ?
C4 C3 C2 C1 0.0(6) . . . . ?
C4 C7 C8 Br1 179.8(3) . . . . ?
C1 C6 C5 C4 -1.3(6) . . . . ?
C8 C7 C4 C3 -144.9(5) . . . . ?
C8 C7 C4 C5 33.9(6) . . . . ?

_shelx_res_file                  
;
    20211208hl_0m_a.res created by SHELXL-2014/7

TITL
CELL 1.34139 8.4516 12.1323 9.7322 90 110.762 90
ZERR 4 0.0005 0.0007 0.0006 0 0.002 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H Br N O
DISP Br -0.9338 1.0006 7840.1
DISP C 0.0137 0.0067 57.1
DISP H 0 0 0.6
DISP N 0.0241 0.0134 109.9
DISP O 0.0389 0.0241 193.4
UNIT 32 20 8 4 8

L.S. 4
PLAN  20
TEMP -173.15
CONF
more -4
fmap 2
acta
REM <olex2.extras>
REM <HklSrc "%.\\20211208hL_0m_a.hkl">
REM </olex2.extras>

WGHT    0.051300    1.696100
FVAR       0.31301
BR2   3    0.005292    0.698593    0.063295    11.00000    0.02255    0.02710 =
         0.03399    0.00080    0.01299    0.00468
BR1   3   -0.250999    0.501446    0.124500    11.00000    0.04398    0.01858 =
         0.02920    0.00139    0.01823    0.00278
O1    5   -0.435249    1.215824    0.199427    11.00000    0.03310    0.02702 =
         0.03137   -0.00117    0.01870    0.00635
N1    4   -0.357825    1.187694    0.119485    11.00000    0.02202    0.02303 =
         0.02469   -0.00296    0.00988   -0.00195
C3    1   -0.192860    0.927313    0.018706    11.00000    0.02298    0.02007 =
         0.01961   -0.00046    0.01030   -0.00038
AFIX  43
H3    2   -0.138174    0.903050   -0.045956    11.00000   -1.20000
AFIX   0
C6    1   -0.353032    0.998134    0.209167    11.00000    0.02161    0.02575 =
         0.02083   -0.00171    0.00788    0.00063
AFIX  43
H6    2   -0.408471    1.023089    0.272934    11.00000   -1.20000
AFIX   0
O2    5   -0.316284    1.251889    0.041033    11.00000    0.03946    0.02155 =
         0.03827    0.00417    0.02379    0.00288
C2    1   -0.235222    1.037521    0.020799    11.00000    0.02030    0.01908 =
         0.02205   -0.00120    0.00917   -0.00444
AFIX  43
H2    2   -0.210141    1.089265   -0.041857    11.00000   -1.20000
AFIX   0
C5    1   -0.308777    0.888229    0.207585    11.00000    0.02305    0.02419 =
         0.01994    0.00224    0.01067   -0.00459
AFIX  43
H5    2   -0.331978    0.837459    0.272332    11.00000   -1.20000
AFIX   0
C7    1   -0.190980    0.732891    0.107086    11.00000    0.02051    0.02357 =
         0.02000   -0.00150    0.00962    0.00054
C4    1   -0.230265    0.851562    0.111421    11.00000    0.01846    0.01820 =
         0.02082   -0.00059    0.00444   -0.00121
C1    1   -0.314694    1.070551    0.115921    11.00000    0.02074    0.01921 =
         0.01949   -0.00229    0.00328    0.00106
C8    1   -0.288944    0.653331    0.128379    11.00000    0.03054    0.02103 =
         0.02792    0.00102    0.01526    0.00440
AFIX  43
H8    2   -0.386977    0.675822    0.147246    11.00000   -1.20000
AFIX   0
HKLF 4

REM
REM R1 =  0.0368 for    1486 Fo > 4sig(Fo)  and  0.0466 for all    1774 data
REM    118 parameters refined using      0 restraints

END

WGHT      0.0512      1.7062

REM Highest difference peak  0.823,  deepest hole -1.023,  1-sigma level  0.142
Q1    1   0.1079  0.7088  0.0586  11.00000  0.05    0.82
Q2    1  -0.3984  0.5845  0.0929  11.00000  0.05    0.76
Q3    1  -0.1325  0.5015  0.1444  11.00000  0.05    0.64
Q4    1  -0.1207  0.7029  0.0701  11.00000  0.05    0.47
Q5    1   0.0656  0.6917  0.2477  11.00000  0.05    0.46
Q6    1  -0.0087  0.6978 -0.0765  11.00000  0.05    0.44
Q7    1   0.1507  0.7018  0.1628  11.00000  0.05    0.44
Q8    1  -0.2873  0.7045  0.0447  11.00000  0.05    0.44
Q9    1  -0.1678  0.9574  0.3103  11.00000  0.05    0.42
Q10   1  -0.4086  0.5035  0.0839  11.00000  0.05    0.41
Q11   1  -0.3996  0.4212  0.0797  11.00000  0.05    0.40
Q12   1  -0.4013  0.9033  0.0046  11.00000  0.05    0.39
Q13   1  -0.0319  0.8068  0.3064  11.00000  0.05    0.38
Q14   1  -0.1981  0.8993 -0.1697  11.00000  0.05    0.38
Q15   1  -0.2721  0.4985 -0.0298  11.00000  0.05    0.37
Q16   1  -0.6064  1.2469  0.0887  11.00000  0.05    0.37
Q17   1  -0.2388  0.8038  0.0971  11.00000  0.05    0.37
Q18   1  -0.1759  1.1012 -0.1698  11.00000  0.05    0.36
Q19   1  -0.3186  1.0095  0.3572  11.00000  0.05    0.36
Q20   1  -0.4560  1.3573  0.0968  11.00000  0.05    0.36
;
_shelx_res_checksum              10045
_olex2_submission_special_instructions 'No special instructions were received'
