# Electronic Supplementary Material (ESI) for ChemComm.
# 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. 
# 
#######################################################################

data_n_c_1_auto_r
_database_code_depnum_ccdc_archive 'CCDC 2215497'
loop_
_audit_author_name
_audit_author_address
N-Cl
;Southeast University
China
;
_audit_update_record             
;
2023-03-21 deposited with the CCDC.	2023-03-22 downloaded from the CCDC.
;
_audit_creation_date             2023-03-20
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Cl, C6 H6 N O2'
_chemical_formula_sum            'C6 H6 Cl N O2'
_chemical_formula_weight         159.57
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C1 H1 N1 O1 Cl1'
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'
Cl Cl 0.1484 0.1585 '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           11
_space_group_name_H-M_alt        'P 1 21/m 1'
_space_group_name_Hall           '-P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'

_cell_length_a                   7.1749(3)
_cell_length_b                   6.6728(3)
_cell_length_c                   7.4888(3)
_cell_angle_alpha                90
_cell_angle_beta                 99.545(4)
_cell_angle_gamma                90
_cell_volume                     353.58(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6064
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      30.6760
_cell_measurement_theta_min      2.7330
_shelx_estimated_absorpt_T_max   0.954
_shelx_estimated_absorpt_T_min   0.911
_exptl_absorpt_coefficient_mu    0.473
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85071
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.84a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.499
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             164
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_av_unetI/netI     0.0137
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            9039
_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         28.280
_diffrn_reflns_theta_min         2.758
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -8.00  76.00   0.50    0.50    --    4.83  77.00  60.00  168
  2  ω     12.00  77.00   0.50    0.50    --    4.83  58.00 -53.00  130
  3  ω     -9.00  18.00   0.50    0.50    --    4.83 -38.00  30.00   54
  4  ω    -48.00 -23.00   0.50    0.50    --    4.83 -58.00 165.00   50
  5  ω    -42.00  18.00   0.50    0.50    --    4.83 -31.00 120.39  120
  6  ω    -64.00  18.00   0.50    0.50    --    4.83 -19.00  60.00  164
  7  ω    -68.00  17.00   0.50    0.50    --    4.83 -19.00 -30.00  170
  8  ω    -61.00  18.00   0.50    0.50    --    4.83 -19.00-180.00  158
  9  ω    -18.00  61.00   0.50    0.50    --   -5.53  19.00 -90.00  158
 10  ω    -19.00  62.00   0.50    0.50    --   -5.53  58.00 -53.00  162
 11  ω    -56.00 -22.00   0.50    0.50    --   -5.53 -58.00 165.00   68
 12  ω     18.00  48.00   0.50    0.50    --    4.83-120.00 148.55   60
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0468791000
_diffrn_orient_matrix_UB_12      0.0794461000
_diffrn_orient_matrix_UB_13      -0.0372134000
_diffrn_orient_matrix_UB_21      0.0393517000
_diffrn_orient_matrix_UB_22      -0.0695283000
_diffrn_orient_matrix_UB_23      -0.0550139000
_diffrn_orient_matrix_UB_31      -0.0794069000
_diffrn_orient_matrix_UB_32      0.0124325000
_diffrn_orient_matrix_UB_33      -0.0693576000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                854
_reflns_number_total             943
_reflns_odcompleteness_completeness 99.47
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22
_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       'CrysAlisPro 1.171.42.84a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.84a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.84a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.315
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     67
_refine_ls_number_reflns         943
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0316
_refine_ls_R_factor_gt           0.0288
_refine_ls_restrained_S_all      1.093
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0382P)²+0.1000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0792
_refine_ls_wR_factor_ref         0.0809
_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:
 C1(H1B), C2(H2), C3(H3), C5(H5)
;
_atom_sites_solution_hydrogens   mixed
_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
Cl1 Cl 0.28102(6) 0.250000 0.85217(6) 0.04112(17) Uani 1 2 d S T P . .
O1 O 0.4449(2) 0.250000 0.52082(18) 0.0533(4) Uani 1 2 d S T P . .
H1 H 0.392(5) 0.250000 0.634(5) 0.091(10) Uiso 1 2 d S . P . .
N1 N 0.7124(2) 0.250000 0.0824(2) 0.0376(4) Uani 1 2 d S T P . .
H1A H 0.640(4) 0.250000 -0.022(3) 0.053(7) Uiso 1 2 d S . P . .
C1 C 0.8991(3) 0.250000 0.0984(3) 0.0454(5) Uani 1 2 d S T P . .
H1B H 0.956289 0.250000 -0.004348 0.055 Uiso 1 2 calc R U P . .
C2 C 1.0076(3) 0.250000 0.2674(3) 0.0518(6) Uani 1 2 d S T P . .
H2 H 1.138755 0.250000 0.280025 0.062 Uiso 1 2 calc R U P . .
O2 O 0.7182(2) 0.250000 0.70926(19) 0.0784(7) Uani 1 2 d S T P . .
C3 C 0.9204(3) 0.250000 0.4188(3) 0.0449(5) Uani 1 2 d S T P . .
H3 H 0.992227 0.250000 0.534225 0.054 Uiso 1 2 calc R U P . .
C4 C 0.7252(3) 0.250000 0.3967(2) 0.0360(4) Uani 1 2 d S T P . .
C5 C 0.6220(3) 0.250000 0.2244(2) 0.0364(4) Uani 1 2 d S T P . .
H5 H 0.490584 0.250000 0.207161 0.044 Uiso 1 2 calc R U P . .
C6 C 0.6293(3) 0.250000 0.5594(2) 0.0428(4) Uani 1 2 d S T P . .


_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
O1 H1 0.98(4) . ?
O1 C6 1.307(2) . ?
N1 H1A 0.87(3) . ?
N1 C1 1.326(3) . ?
N1 C5 1.334(2) . ?
C1 H1B 0.9300 . ?
C1 C2 1.371(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.383(3) . ?
O2 C6 1.195(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.383(3) . ?
C4 C5 1.377(2) . ?
C4 C6 1.495(2) . ?
C5 H5 0.9300 . ?

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
C6 O1 H1 109(2) . . ?
C1 N1 H1A 122.0(17) . . ?
C1 N1 C5 123.08(16) . . ?
C5 N1 H1A 114.9(17) . . ?
N1 C1 H1B 120.2 . . ?
N1 C1 C2 119.61(17) . . ?
C2 C1 H1B 120.2 . . ?
C1 C2 H2 120.3 . . ?
C1 C2 C3 119.47(18) . . ?
C3 C2 H2 120.3 . . ?
C2 C3 H3 120.4 . . ?
C4 C3 C2 119.25(17) . . ?
C4 C3 H3 120.4 . . ?
C3 C4 C6 119.74(16) . . ?
C5 C4 C3 119.27(16) . . ?
C5 C4 C6 120.99(17) . . ?
N1 C5 C4 119.32(17) . . ?
N1 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
O1 C6 C4 113.93(16) . . ?
O2 C6 O1 124.79(17) . . ?
O2 C6 C4 121.27(18) . . ?

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
N1 C1 C2 C3 0.000(0) . . . . ?
C1 N1 C5 C4 0.000(0) . . . . ?
C1 C2 C3 C4 0.000(0) . . . . ?
C2 C3 C4 C5 0.000(0) . . . . ?
C2 C3 C4 C6 180.000(0) . . . . ?
C3 C4 C5 N1 0.000(0) . . . . ?
C3 C4 C6 O1 180.000(0) . . . . ?
C3 C4 C6 O2 0.000(0) . . . . ?
C5 N1 C1 C2 0.000(0) . . . . ?
C5 C4 C6 O1 0.000(0) . . . . ?
C5 C4 C6 O2 180.000(0) . . . . ?
C6 C4 C5 N1 180.000(0) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.361
_oxdiff_exptl_absorpt_empirical_full_min 0.810
####################################################################### 
# 
# 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_111
_database_code_depnum_ccdc_archive 'CCDC 2215499'
loop_
_audit_author_name
_audit_author_address
Jie
;Southeast University
China
;
_audit_update_record             
;
2023-03-21 deposited with the CCDC.	2023-03-22 downloaded from the CCDC.
;
_audit_creation_date             2023-03-21
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Br, C6 H6 N O2'
_chemical_formula_sum            'C6 H6 Br N O2'
_chemical_formula_weight         204.03
_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      monoclinic
_space_group_IT_number           11
_space_group_name_H-M_alt        'P 1 21/m 1'
_space_group_name_Hall           '-P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'

_cell_length_a                   7.4792(5)
_cell_length_b                   6.9912(7)
_cell_length_c                   7.5202(4)
_cell_angle_alpha                90
_cell_angle_beta                 100.036(6)
_cell_angle_gamma                90
_cell_volume                     387.20(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1021
_cell_measurement_temperature    413
_cell_measurement_theta_max      29.5510
_cell_measurement_theta_min      2.7280
_shelx_estimated_absorpt_T_max   0.622
_shelx_estimated_absorpt_T_min   0.420
_exptl_absorpt_coefficient_mu    5.247
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.23639
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.750
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             200
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0151
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_Laue_measured_fraction_full 0.946
_diffrn_reflns_Laue_measured_fraction_max 0.938
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            1702
_diffrn_reflns_point_group_measured_fraction_full 0.946
_diffrn_reflns_point_group_measured_fraction_max 0.938
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.727
_diffrn_reflns_theta_min         2.751
_diffrn_ambient_temperature      413
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.946
_diffrn_measured_fraction_theta_max 0.938
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                619
_reflns_number_total             835
_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 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.830
_refine_diff_density_min         -0.442
_refine_diff_density_rms         0.075
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     74
_refine_ls_number_reflns         835
_refine_ls_number_restraints     11
_refine_ls_R_factor_all          0.0538
_refine_ls_R_factor_gt           0.0375
_refine_ls_restrained_S_all      0.987
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0710P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0996
_refine_ls_wR_factor_ref         0.1045
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 O1A-H1 = O1-H1
 0.93 with sigma of 0.003
3. Uiso/Uaniso restraints and constraints
Uanis(O1) = Uanis(O1A)
Uanis(O2A) = Uanis(O2)
4. Rigid body (RIGU) restrains
 O1, O2, C6
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(O1A)=Sof(O2A)=0.5*(1-FVAR(2))
 Sof(O1)=Sof(O2)=0.5*FVAR(2)
6.a Aromatic/amide H refined with riding coordinates:
 C1(H1B), C2(H2), C3(H3), C5(H5)
;
_atom_sites_solution_hydrogens   mixed
_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 0.28042(7) 0.750000 0.85623(7) 0.0739(3) Uani 1 2 d S T P . .
O1 O 0.453(7) 0.750000 0.508(3) 0.078(7) Uani 0.42(15) 2 d DS T P A 1
H1 H 0.423(11) 0.750000 0.623(6) 0.18(4) Uiso 1 2 d DS . P . .
O1A O 0.472(5) 0.703(8) 0.525(4) 0.078(7) Uani 0.29(7) 1 d D . P A 2
N1 N 0.7220(7) 0.750000 0.0894(7) 0.0693(14) Uani 1 2 d S T P . .
H1A H 0.663(11) 0.750000 -0.004(10) 0.09(2) Uiso 1 2 d S . P . .
C1 C 0.9014(8) 0.750000 0.1066(8) 0.0764(17) Uani 1 2 d S T P . .
H1B H 0.956498 0.750000 0.004838 0.092 Uiso 1 2 calc R U P . .
O2 O 0.736(11) 0.750000 0.714(6) 0.099(12) Uani 0.42(15) 2 d S T P A 1
O2A O 0.710(7) 0.801(14) 0.706(4) 0.099(12) Uani 0.29(7) 1 d . . P A 2
C2 C 1.0045(8) 0.750000 0.2754(8) 0.093(2) Uani 1 2 d S T P . .
H2 H 1.130524 0.750000 0.289841 0.112 Uiso 1 2 calc R U P . .
C3 C 0.9204(8) 0.750000 0.4233(8) 0.0821(19) Uani 1 2 d S T P . .
H3 H 0.988999 0.750000 0.539003 0.098 Uiso 1 2 calc R U P . .
C4 C 0.7339(8) 0.750000 0.3997(7) 0.0655(15) Uani 1 2 d S T P A .
C5 C 0.6367(8) 0.750000 0.2283(7) 0.0649(15) Uani 1 2 d S T P . .
H5 H 0.510428 0.750000 0.209767 0.078 Uiso 1 2 calc R U P . .
C6 C 0.6394(8) 0.750000 0.5592(7) 0.0782(19) Uani 1 2 d S T P . .


_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
O1 H1 0.930(3) . ?
O1 C6 1.38(5) . ?
O1A H1 0.930(3) . ?
O1A O1A 0.66(11) 4_575 ?
O1A C6 1.28(4) . ?
N1 H1A 0.76(8) . ?
N1 C1 1.325(8) . ?
N1 C5 1.316(7) . ?
C1 H1B 0.9300 . ?
C1 C2 1.366(8) . ?
O2 C6 1.26(5) . ?
O2A O2A 0.71(19) 4_575 ?
O2A C6 1.19(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.370(8) . ?
C3 H3 0.9300 . ?
C3 C4 1.375(8) . ?
C4 C5 1.365(7) . ?
C4 C6 1.494(8) . ?
C5 H5 0.9300 . ?

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
C6 O1 H1 98(6) . . ?
O1A O1A H1 69(4) 4_575 . ?
O1A O1A C6 75(2) 4_575 . ?
C6 O1A H1 105(7) . . ?
C1 N1 H1A 120(6) . . ?
C5 N1 H1A 116(6) . . ?
C5 N1 C1 123.1(6) . . ?
N1 C1 H1B 120.4 . . ?
N1 C1 C2 119.2(6) . . ?
C2 C1 H1B 120.4 . . ?
O2A O2A C6 73(4) 4_575 . ?
C1 C2 H2 120.3 . . ?
C1 C2 C3 119.4(6) . . ?
C3 C2 H2 120.3 . . ?
C2 C3 H3 120.2 . . ?
C2 C3 C4 119.6(5) . . ?
C4 C3 H3 120.2 . . ?
C3 C4 C6 120.5(5) . . ?
C5 C4 C3 118.9(5) . . ?
C5 C4 C6 120.6(5) . . ?
N1 C5 C4 119.8(5) . . ?
N1 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
O1 C6 C4 111.7(8) . . ?
O1A C6 C4 115.2(10) 4_575 . ?
O1A C6 C4 115.2(10) . . ?
O2 C6 O1 130(4) . . ?
O2 C6 O1A 125(4) . 4_575 ?
O2 C6 C4 118(3) . . ?
O2A C6 O1A 111(3) 4_575 . ?
O2A C6 O1A 121(3) . . ?
O2A C6 O2A 35(9) 4_575 . ?
O2A C6 C4 123(3) 4_575 . ?
O2A C6 C4 123(3) . . ?

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
_geom_hbond_publ_flag
N1 H1A O2 0.76(8) 2.28(9) 2.85(4) 131(8) 1_554 yes

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
O1A O1A C6 O2A 79(5) 4_575 . . . ?
O1A O1A C6 O2A 116(5) 4_575 . . 4_575 ?
O1A O1A C6 C4 -97.2(14) 4_575 . . . ?
N1 C1 C2 C3 0.000(1) . . . . ?
C1 N1 C5 C4 0.000(1) . . . . ?
C1 C2 C3 C4 0.000(1) . . . . ?
O2A O2A C6 O1A 114(3) 4_575 . . 4_575 ?
O2A O2A C6 O1A 83(3) 4_575 . . . ?
O2A O2A C6 C4 -102(3) 4_575 . . . ?
C2 C3 C4 C5 0.000(1) . . . . ?
C2 C3 C4 C6 180.000(1) . . . . ?
C3 C4 C5 N1 0.000(1) . . . . ?
C3 C4 C6 O1 180.000(8) . . . . ?
C3 C4 C6 O1A 163(3) . . . 4_575 ?
C3 C4 C6 O1A -163(3) . . . . ?
C3 C4 C6 O2 0.000(16) . . . . ?
C3 C4 C6 O2A -21(5) . . . 4_575 ?
C3 C4 C6 O2A 21(5) . . . . ?
C5 N1 C1 C2 0.000(1) . . . . ?
C5 C4 C6 O1 0.000(8) . . . . ?
C5 C4 C6 O1A -17(3) . . . 4_575 ?
C5 C4 C6 O1A 17(3) . . . . ?
C5 C4 C6 O2 180.000(16) . . . . ?
C5 C4 C6 O2A 159(5) . . . 4_575 ?
C5 C4 C6 O2A -159(5) . . . . ?
C6 C4 C5 N1 180.000(1) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
# start Validation Reply Form
_vrf_PLAT029_111                 
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.946 Why?  
RESPONSE: The high angle diffraction data were not very good since
  the structure is disordered at high temperature.
;
# end Validation Reply Form
####################################################################### 
# 
# 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_n_b_q_auto_r
_database_code_depnum_ccdc_archive 'CCDC 2215498'
loop_
_audit_author_name
_audit_author_address
JIe
;Southeast University
China
;
_audit_update_record             
;
2023-03-21 deposited with the CCDC.	2023-03-22 downloaded from the CCDC.
;
_audit_creation_date             2023-03-21
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(Br), 2(C6 H6 N O2)'
_chemical_formula_sum            'C12 H12 Br2 N2 O4'
_chemical_formula_weight         408.06
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C1 H1 N1 O1 Br1'
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.0700(7)
_cell_length_b                   7.4103(6)
_cell_length_c                   7.5264(7)
_cell_angle_alpha                79.944(7)
_cell_angle_beta                 86.365(7)
_cell_angle_gamma                68.488(8)
_cell_volume                     361.21(6)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    4031
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.5760
_cell_measurement_theta_min      2.7610
_shelx_estimated_absorpt_T_max   0.603
_shelx_estimated_absorpt_T_min   0.603
_exptl_absorpt_coefficient_mu    5.624
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.30463
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.84a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.876
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             200
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0667
_diffrn_reflns_av_unetI/netI     0.0571
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            8083
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.877
_diffrn_reflns_theta_min         2.749
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -46.00  16.00   0.50    0.50    --    4.98 -38.00 120.00  124
  2  ω    -18.00  28.00   0.50    0.50    --    4.98 -78.00  89.00   92
  3  ω    -15.00  30.00   0.50    0.50    --    4.98 -99.00   0.00   90
  4  ω     12.00  42.00   0.50    0.50    --    4.98  78.00-145.00   60
  5  ω    -61.00  18.00   0.50    0.50    --    4.98 -38.00   0.00  158
  6  ω    -69.00  17.00   0.50    0.50    --    4.98 -19.00  60.00  172
  7  ω     -8.00  48.00   0.50    0.50    --    4.98  19.00 150.00  112
  8  ω    -34.00  16.00   0.50    0.50    --   -5.77 -78.00  89.00  100
  9  ω    -75.00   5.00   0.50    0.50    --   -5.77 -38.00 -90.00  160
 10  ω    -18.00  10.00   0.50    0.50    --   -5.77  38.00-150.00   56
 11  ω     16.00  67.00   0.50    0.50    --   -5.77  38.00-150.00  102
 12  ω    -29.00  43.00   0.50    0.50    --   -5.77  78.00-145.00  144
 13  ω    -19.00  54.00   0.50    0.50    --   -5.77  38.00 -60.00  146
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0720808000
_diffrn_orient_matrix_UB_12      -0.0077607000
_diffrn_orient_matrix_UB_13      -0.0709783000
_diffrn_orient_matrix_UB_21      0.0537827000
_diffrn_orient_matrix_UB_22      -0.0993283000
_diffrn_orient_matrix_UB_23      0.0379747000
_diffrn_orient_matrix_UB_31      -0.0595022000
_diffrn_orient_matrix_UB_32      -0.0307872000
_diffrn_orient_matrix_UB_33      -0.0517768000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1474
_reflns_number_total             1695
_reflns_odcompleteness_completeness 98.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.82
_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       'CrysAlisPro 1.171.42.84a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.84a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.84a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.236
_refine_diff_density_min         -0.998
_refine_diff_density_rms         0.147
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     92
_refine_ls_number_reflns         1695
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1065
_refine_ls_R_factor_gt           0.0902
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0174P)²+7.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1632
_refine_ls_wR_factor_ref         0.1692
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1A), C1(H1B), C2(H2), C3(H3), C5(H5)
2.b Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_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 0.79666(16) 0.03791(13) 0.26480(12) 0.0354(3) Uani 1 1 d . . . . .
O1 O 0.7750(12) 0.3832(9) 0.4530(8) 0.0444(17) Uani 1 1 d . . . . .
H1 H 0.769922 0.292288 0.407631 0.067 Uiso 1 1 calc R U . . .
N1 N 0.7505(12) 0.8277(10) 0.7096(10) 0.0337(17) Uani 1 1 d . . . . .
H1A H 0.758281 0.933944 0.647850 0.040 Uiso 1 1 calc R U . . .
C1 C 0.7458(15) 0.8094(14) 0.8893(13) 0.039(2) Uani 1 1 d . . . . .
H1B H 0.749254 0.910980 0.944700 0.047 Uiso 1 1 calc R U . . .
C2 C 0.7361(15) 0.6419(14) 0.9919(12) 0.039(2) Uani 1 1 d . . . . .
H2 H 0.734544 0.627198 1.117226 0.047 Uiso 1 1 calc R U . . .
O2 O 0.6620(11) 0.2341(9) 0.6977(9) 0.0420(16) Uani 1 1 d . . . . .
C3 C 0.7285(14) 0.4949(13) 0.9058(12) 0.0329(19) Uani 1 1 d . . . . .
H3 H 0.722060 0.379681 0.973543 0.039 Uiso 1 1 calc R U . . .
C4 C 0.7304(12) 0.5180(11) 0.7186(11) 0.0253(17) Uani 1 1 d . . . . .
C5 C 0.7435(14) 0.6889(12) 0.6214(12) 0.0310(19) Uani 1 1 d . . . . .
H5 H 0.747438 0.707201 0.495997 0.037 Uiso 1 1 calc R U . . .
C6 C 0.7192(13) 0.3629(12) 0.6241(12) 0.0291(18) Uani 1 1 d . . . . .


_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
O1 H1 0.8200 . ?
O1 C6 1.322(10) . ?
N1 H1A 0.8600 . ?
N1 C1 1.335(12) . ?
N1 C5 1.335(10) . ?
C1 H1B 0.9300 . ?
C1 C2 1.365(13) . ?
C2 H2 0.9300 . ?
C2 C3 1.379(12) . ?
O2 C6 1.205(10) . ?
C3 H3 0.9300 . ?
C3 C4 1.389(12) . ?
C4 C5 1.379(10) . ?
C4 C6 1.481(11) . ?
C5 H5 0.9300 . ?

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
C6 O1 H1 109.5 . . ?
C1 N1 H1A 118.5 . . ?
C5 N1 H1A 118.5 . . ?
C5 N1 C1 123.1(7) . . ?
N1 C1 H1B 119.9 . . ?
N1 C1 C2 120.1(8) . . ?
C2 C1 H1B 119.9 . . ?
C1 C2 H2 120.7 . . ?
C1 C2 C3 118.6(8) . . ?
C3 C2 H2 120.7 . . ?
C2 C3 H3 119.8 . . ?
C2 C3 C4 120.4(8) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 C6 121.1(7) . . ?
C5 C4 C3 118.6(8) . . ?
C5 C4 C6 120.3(7) . . ?
N1 C5 C4 119.1(8) . . ?
N1 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?
O1 C6 C4 113.1(7) . . ?
O2 C6 O1 124.5(8) . . ?
O2 C6 C4 122.4(8) . . ?

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
N1 C1 C2 C3 -0.8(15) . . . . ?
C1 N1 C5 C4 0.2(14) . . . . ?
C1 C2 C3 C4 -0.1(14) . . . . ?
C2 C3 C4 C5 1.1(13) . . . . ?
C2 C3 C4 C6 -179.0(8) . . . . ?
C3 C4 C5 N1 -1.1(13) . . . . ?
C3 C4 C6 O1 -163.4(8) . . . . ?
C3 C4 C6 O2 17.5(13) . . . . ?
C5 N1 C1 C2 0.8(15) . . . . ?
C5 C4 C6 O1 16.4(12) . . . . ?
C5 C4 C6 O2 -162.7(9) . . . . ?
C6 C4 C5 N1 179.0(8) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.944
_oxdiff_exptl_absorpt_empirical_full_min 0.612
####################################################################### 
# 
# 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_n_i_sphere_auto-r
_database_code_depnum_ccdc_archive 'CCDC 2215500'
loop_
_audit_author_name
_audit_author_address
Jie
;Southeast University
China
;
_audit_update_record             
;
2023-03-21 deposited with the CCDC.	2023-03-22 downloaded from the CCDC.
;
_audit_creation_date             2023-03-20
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(I), 2(C6 H6 N O2)'
_chemical_formula_sum            'C12 H12 I2 N2 O4'
_chemical_formula_weight         502.04
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C1 H1 N1 O1 I1'
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'
I I -0.4742 1.8119 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.4174(5)
_cell_length_b                   7.4195(7)
_cell_length_c                   8.1011(7)
_cell_angle_alpha                81.904(7)
_cell_angle_beta                 79.902(6)
_cell_angle_gamma                67.021(7)
_cell_volume                     402.80(6)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    7449
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      31.1040
_cell_measurement_theta_min      2.5330
_shelx_estimated_absorpt_T_max   0.591
_shelx_estimated_absorpt_T_min   0.508
_exptl_absorpt_coefficient_mu    3.916
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.28863
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.84a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.070
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             236
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0375
_diffrn_reflns_av_unetI/netI     0.0201
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            9155
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.875
_diffrn_reflns_theta_min         2.562
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -26.00  -1.00   0.50    0.50    --    4.98 -88.00 -49.00   50
  2  ω    -31.00   1.00   0.50    0.50    --   -5.77 -88.00 -49.00   64
  3  ω    -20.00   7.00   0.50    0.50    --   -5.77  33.00 -35.92   54
  4  ω     38.00  63.00   0.50    0.50    --   -5.77  33.00 -35.92   50
  5  ω      6.00  42.00   0.50    0.50    --   -5.77  88.00  66.00   72
  6  ω    -22.00  38.00   0.50    0.50    --    4.98  88.00  66.00  120
  7  ω     -9.00  77.00   0.50    0.50    --    4.98  57.00-120.00  172
  8  ω    -10.00  17.00   0.50    0.50    --    4.98 -38.00-120.00   54
  9  ω    -64.00 -12.00   0.50    0.50    --    4.98 -38.00-120.00  104
 10  ω    -58.00 -31.00   0.50    0.50    --    4.98 -19.00-180.00   54
 11  ω    -26.00  17.00   0.50    0.50    --    4.98 -19.00-180.00   86
 12  ω    -63.00  18.00   0.50    0.50    --    4.98 -19.00 -90.00  162
 13  ω    -70.00  18.00   0.50    0.50    --    4.98 -19.00   0.00  176
 14  ω    -70.00  18.00   0.50    0.50    --    4.98 -19.00  90.00  176
 15  ω    -42.00  18.00   0.50    0.50    --    4.98 -31.00 145.67  120
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0091877000
_diffrn_orient_matrix_UB_12      -0.0523324000
_diffrn_orient_matrix_UB_13      0.0792951000
_diffrn_orient_matrix_UB_21      -0.1027455000
_diffrn_orient_matrix_UB_22      0.0570348000
_diffrn_orient_matrix_UB_23      0.0119334000
_diffrn_orient_matrix_UB_31      -0.0184134000
_diffrn_orient_matrix_UB_32      -0.0697152000
_diffrn_orient_matrix_UB_33      -0.0391133000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1785
_reflns_number_total             1903
_reflns_odcompleteness_completeness 99.11
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.82
_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       'CrysAlisPro 1.171.42.84a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.84a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.84a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         1.501
_refine_diff_density_min         -1.445
_refine_diff_density_rms         0.143
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     96
_refine_ls_number_reflns         1903
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0383
_refine_ls_R_factor_gt           0.0358
_refine_ls_restrained_S_all      1.096
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0525P)²+0.6000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0899
_refine_ls_wR_factor_ref         0.0910
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C5(H5)
2.b Idealised tetrahedral OH refined as rotating group:
 O1(H1A)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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
I1 I 0.53493(4) 1.29744(4) -0.23922(3) 0.04496(13) Uani 1 1 d . . . . .
C1 C 1.3061(8) 1.2474(8) 0.3867(7) 0.0535(12) Uani 1 1 d . . . . .
H1 H 1.405434 1.252053 0.439863 0.064 Uiso 1 1 calc R U . . .
O1 O 0.8941(6) 1.2687(7) -0.0280(5) 0.0615(10) Uani 1 1 d . . . . .
H1A H 0.804662 1.264945 -0.072533 0.092 Uiso 1 1 calc R U . . .
N1 N 1.3284(6) 1.2492(7) 0.2217(6) 0.0481(9) Uani 1 1 d . . . . .
H1B H 1.433(9) 1.252(9) 0.172(8) 0.054(16) Uiso 1 1 d . . . . .
C2 C 1.1367(8) 1.2385(9) 0.4798(7) 0.0547(12) Uani 1 1 d . . . . .
H2 H 1.119805 1.237840 0.596334 0.066 Uiso 1 1 calc R U . . .
O2 O 0.7381(5) 1.1647(6) 0.2055(5) 0.0539(8) Uani 1 1 d . . . . .
C3 C 0.9906(7) 1.2305(8) 0.3992(6) 0.0469(10) Uani 1 1 d . . . . .
H3 H 0.874814 1.223898 0.460781 0.056 Uiso 1 1 calc R U . . .
C4 C 1.0194(6) 1.2325(6) 0.2257(5) 0.0369(8) Uani 1 1 d . . . . .
C5 C 1.1920(6) 1.2434(7) 0.1373(6) 0.0427(9) Uani 1 1 d . . . . .
H5 H 1.212932 1.246554 0.020558 0.051 Uiso 1 1 calc R U . . .
C6 C 0.8678(6) 1.2176(7) 0.1341(6) 0.0409(9) Uani 1 1 d . . . . .


_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
C1 H1 0.9300 . ?
C1 N1 1.316(7) . ?
C1 C2 1.368(8) . ?
O1 H1A 0.8200 . ?
O1 C6 1.316(6) . ?
N1 H1B 0.82(6) . ?
N1 C5 1.334(6) . ?
C2 H2 0.9300 . ?
C2 C3 1.382(7) . ?
O2 C6 1.205(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.383(7) . ?
C4 C5 1.378(6) . ?
C4 C6 1.497(6) . ?
C5 H5 0.9300 . ?

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
N1 C1 H1 120.0 . . ?
N1 C1 C2 119.9(4) . . ?
C2 C1 H1 120.0 . . ?
C6 O1 H1A 109.5 . . ?
C1 N1 H1B 116(5) . . ?
C1 N1 C5 123.2(4) . . ?
C5 N1 H1B 120(5) . . ?
C1 C2 H2 120.3 . . ?
C1 C2 C3 119.5(5) . . ?
C3 C2 H2 120.3 . . ?
C2 C3 H3 120.5 . . ?
C2 C3 C4 119.0(4) . . ?
C4 C3 H3 120.5 . . ?
C3 C4 C6 120.7(4) . . ?
C5 C4 C3 119.4(4) . . ?
C5 C4 C6 119.9(4) . . ?
N1 C5 C4 119.1(4) . . ?
N1 C5 H5 120.5 . . ?
C4 C5 H5 120.5 . . ?
O1 C6 C4 112.5(4) . . ?
O2 C6 O1 125.6(4) . . ?
O2 C6 C4 121.9(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
C1 N1 C5 C4 -0.8(8) . . . . ?
C1 C2 C3 C4 -0.3(8) . . . . ?
N1 C1 C2 C3 0.3(9) . . . . ?
C2 C1 N1 C5 0.2(8) . . . . ?
C2 C3 C4 C5 -0.3(7) . . . . ?
C2 C3 C4 C6 178.0(5) . . . . ?
C3 C4 C5 N1 0.8(7) . . . . ?
C3 C4 C6 O1 164.6(5) . . . . ?
C3 C4 C6 O2 -15.1(7) . . . . ?
C5 C4 C6 O1 -17.0(6) . . . . ?
C5 C4 C6 O2 163.2(5) . . . . ?
C6 C4 C5 N1 -177.5(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.806
_oxdiff_exptl_absorpt_empirical_full_min 0.540
