# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_n01
_database_code_depnum_ccdc_archive 'CCDC 2041337'
loop_
_audit_author_name
_audit_author_address
Duan
;Nanjingxiaozhuang university
China
;
_audit_update_record             
;
2020-10-29 deposited with the CCDC.	2021-09-01 downloaded from the CCDC.
;
_audit_creation_date             2019-04-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'I3, C5 H7 N2'
_chemical_formula_sum            'C5 H7 I3 N2'
_chemical_formula_weight         475.83
_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'
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'

_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                   7.9381(6)
_cell_length_b                   8.3518(9)
_cell_length_c                   9.1264(9)
_cell_angle_alpha                79.736(9)
_cell_angle_beta                 88.578(7)
_cell_angle_gamma                64.587(9)
_cell_volume                     536.86(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2247
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      29.3260
_cell_measurement_theta_min      2.8600
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    8.677
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.37950
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            bronze
_exptl_crystal_density_diffrn    2.944
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_av_unetI/netI     0.0436
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.833
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            4033
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.833
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.442
_diffrn_reflns_theta_min         2.272
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.833
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -53.00  40.00   1.00    1.00    --   11.74 -57.00  90.00   93
  2  ω    -13.00  79.00   1.00    1.00    --   11.74  77.00   0.00   92
  3  ω     -8.00  83.00   1.00    1.00    --   11.74  57.00-120.00   91
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0269978000
_diffrn_orient_matrix_UB_12      0.0731083000
_diffrn_orient_matrix_UB_13      0.0385598000
_diffrn_orient_matrix_UB_21      0.0920961000
_diffrn_orient_matrix_UB_22      -0.0363842000
_diffrn_orient_matrix_UB_23      0.0325741000
_diffrn_orient_matrix_UB_31      0.0246771000
_diffrn_orient_matrix_UB_32      0.0498735000
_diffrn_orient_matrix_UB_33      -0.0609229000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2158
_reflns_number_total             2480
_reflns_odcompleteness_completeness 99.73
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.002
_refine_diff_density_min         -1.237
_refine_diff_density_rms         0.225
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     92
_refine_ls_number_reflns         2480
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0369
_refine_ls_R_factor_gt           0.0302
_refine_ls_restrained_S_all      1.050
_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)+(0.0223P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0618
_refine_ls_wR_factor_ref         0.0664
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
2.a Rotating group:
 N2(H2A,H2B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C5(H5), C3(H3), C4(H4), C2(H2)
;
_atom_sites_solution_hydrogens   mixed
_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
I2 I 0.18630(4) 0.64472(4) 0.42317(4) 0.01296(10) Uani 1 1 d . . . . .
I3 I 0.27223(5) 0.75378(4) 0.69453(4) 0.01849(10) Uani 1 1 d . . . . .
I1 I 0.10925(5) 0.55676(4) 0.14793(4) 0.01707(10) Uani 1 1 d . . . . .
N1 N 0.3241(6) 0.0120(5) 0.2829(5) 0.0143(9) Uani 1 1 d . . . . .
N2 N 0.2577(6) 0.1184(5) 0.3950(5) 0.0179(10) Uani 1 1 d . . . . .
H2A H 0.170820 0.222231 0.356681 0.021 Uiso 1 1 d GR . . . .
H2B H 0.213914 0.065368 0.464452 0.021 Uiso 1 1 d GR . . . .
C1 C 0.2229(7) 0.0499(6) 0.1555(6) 0.0176(11) Uani 1 1 d . . . . .
H1 H 0.106334 0.148292 0.137936 0.021 Uiso 1 1 calc R . . . .
C5 C 0.4951(7) -0.1310(6) 0.3128(6) 0.0188(11) Uani 1 1 d . . . . .
H5 H 0.563024 -0.152497 0.401460 0.023 Uiso 1 1 calc R . . . .
C3 C 0.4655(8) -0.2082(7) 0.0792(6) 0.0206(12) Uani 1 1 d . . . . .
H3 H 0.512030 -0.283928 0.010059 0.025 Uiso 1 1 calc R . . . .
C4 C 0.5666(8) -0.2430(7) 0.2117(7) 0.0219(12) Uani 1 1 d . . . . .
H4 H 0.682528 -0.341859 0.231922 0.026 Uiso 1 1 calc R . . . .
C2 C 0.2937(7) -0.0590(7) 0.0510(6) 0.0199(12) Uani 1 1 d . . . . .
H2 H 0.226087 -0.032282 -0.038915 0.024 Uiso 1 1 calc R . . . .


_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
I2 I3 2.9747(5) . ?
I2 I1 2.8885(5) . ?
N1 N2 1.418(6) . ?
N1 C1 1.340(7) . ?
N1 C5 1.361(6) . ?
C1 C2 1.377(7) . ?
C5 C4 1.369(7) . ?
C3 C4 1.383(8) . ?
C3 C2 1.387(7) . ?

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
I1 I2 I3 176.182(13) . . ?
C1 N1 N2 121.6(4) . . ?
C1 N1 C5 122.2(5) . . ?
C5 N1 N2 116.3(4) . . ?
N1 C1 C2 119.1(5) . . ?
N1 C5 C4 119.7(5) . . ?
C2 C3 C4 119.1(5) . . ?
C5 C4 C3 119.6(5) . . ?
C1 C2 C3 120.3(5) . . ?

_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 1.959
_oxdiff_exptl_absorpt_empirical_full_min 0.677
####################################################################### 
# 
# 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_d2
_database_code_depnum_ccdc_archive 'CCDC 2041340'
loop_
_audit_author_name
_audit_author_address
Duan
;Nanjingxiaozhuang university
China
;
_audit_update_record             
;
2020-10-29 deposited with the CCDC.	2021-09-01 downloaded from the CCDC.
;
_audit_creation_date             2019-09-20
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r5938)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'I3, C12 H10 Br N2'
_chemical_formula_sum            'C12 H10 Br I3 N2'
_chemical_formula_weight         642.83
_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'
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'

_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                   12.8074(5)
_cell_length_b                   14.9333(6)
_cell_length_c                   8.4726(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.583(3)
_cell_angle_gamma                90
_cell_volume                     1619.82(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3657
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      28.9750
_cell_measurement_theta_min      2.7740
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    8.241
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63506
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.636
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1160
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_av_unetI/netI     0.0451
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            6678
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         2.095
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -15.00  78.00   1.00    1.30    --   11.74  57.00-180.00   93
  2  ω    -60.00  29.00   1.00    1.30    --   11.74 -57.00  30.00   89
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0319239000
_diffrn_orient_matrix_UB_12      0.0359215000
_diffrn_orient_matrix_UB_13      -0.0273413000
_diffrn_orient_matrix_UB_21      -0.0359835000
_diffrn_orient_matrix_UB_22      -0.0091361000
_diffrn_orient_matrix_UB_23      0.0601466000
_diffrn_orient_matrix_UB_31      0.0274782000
_diffrn_orient_matrix_UB_32      0.0297158000
_diffrn_orient_matrix_UB_33      0.0514483000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2520
_reflns_number_total             2839
_reflns_odcompleteness_completeness 99.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS n/a (Sheldrick, 2008)'
_refine_diff_density_max         1.162
_refine_diff_density_min         -0.866
_refine_diff_density_rms         0.180
_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     163
_refine_ls_number_reflns         2839
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0337
_refine_ls_R_factor_gt           0.0284
_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)+(0.0207P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0575
_refine_ls_wR_factor_ref         0.0605
_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:
 C8(H8), C11(H11), C12(H12), C10(H10), C9(H9), C7(H7), C3(H3), C5(H5), C4(H4),
 C6(H6)
;
_atom_sites_solution_hydrogens   geom
_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
I2 I 0.92863(2) 0.68125(2) 0.96818(4) 0.01279(10) Uani 1 1 d . . . . .
I1 I 0.72522(3) 0.71696(2) 0.82451(4) 0.01425(11) Uani 1 1 d . . . . .
I3 I 1.13822(3) 0.64597(2) 1.10594(4) 0.01712(11) Uani 1 1 d . . . . .
Br1 Br 0.46584(4) 0.70116(3) 0.59541(7) 0.01785(14) Uani 1 1 d . . . . .
N2 N 0.7761(3) 0.4817(3) 0.5141(5) 0.0115(10) Uani 1 1 d . . . . .
N1 N 0.6903(3) 0.4715(3) 0.6156(5) 0.0124(10) Uani 1 1 d . . . . .
C8 C 0.8172(4) 0.5614(3) 0.4735(6) 0.0119(11) Uani 1 1 d . . . . .
H8 H 0.791564 0.614180 0.515917 0.014 Uiso 1 1 calc R U . . .
C11 C 0.8953(4) 0.4039(3) 0.3579(6) 0.0153(12) Uani 1 1 d . . . . .
H11 H 0.922382 0.350507 0.320004 0.018 Uiso 1 1 calc R U . . .
C12 C 0.8152(4) 0.4028(3) 0.4636(6) 0.0128(12) Uani 1 1 d . . . . .
H12 H 0.788610 0.348787 0.499519 0.015 Uiso 1 1 calc R U . . .
C10 C 0.9348(4) 0.4849(3) 0.3090(6) 0.0148(12) Uani 1 1 d . . . . .
H10 H 0.987157 0.486277 0.235193 0.018 Uiso 1 1 calc R U . . .
C9 C 0.8967(4) 0.5637(3) 0.3694(6) 0.0128(12) Uani 1 1 d . . . . .
H9 H 0.925038 0.618269 0.339504 0.015 Uiso 1 1 calc R U . . .
C7 C 0.6203(4) 0.5321(3) 0.6034(6) 0.0118(11) Uani 1 1 d . . . . .
H7 H 0.628001 0.580042 0.534682 0.014 Uiso 1 1 calc R U . . .
C2 C 0.4534(4) 0.5931(3) 0.7122(6) 0.0122(12) Uani 1 1 d . . . . .
C3 C 0.3675(4) 0.5840(4) 0.8078(7) 0.0169(12) Uani 1 1 d . . . . .
H3 H 0.321544 0.631505 0.820444 0.020 Uiso 1 1 calc R U . . .
C5 C 0.4206(4) 0.4333(3) 0.8687(6) 0.0170(12) Uani 1 1 d . . . . .
H5 H 0.407644 0.378861 0.917911 0.020 Uiso 1 1 calc R U . . .
C4 C 0.3513(4) 0.5038(3) 0.8834(7) 0.0188(13) Uani 1 1 d . . . . .
H4 H 0.292932 0.496843 0.945177 0.023 Uiso 1 1 calc R U . . .
C1 C 0.5272(4) 0.5246(3) 0.6999(6) 0.0121(12) Uani 1 1 d . . . . .
C6 C 0.5088(4) 0.4440(3) 0.7809(6) 0.0152(12) Uani 1 1 d . . . . .
H6 H 0.556718 0.397384 0.775061 0.018 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
I2 I1 2.8943(5) . ?
I2 I3 2.9450(5) . ?
Br1 C2 1.902(5) . ?
N2 N1 1.421(5) . ?
N2 C8 1.350(6) . ?
N2 C12 1.355(6) . ?
N1 C7 1.276(6) . ?
C8 H8 0.9300 . ?
C8 C9 1.366(7) . ?
C11 H11 0.9300 . ?
C11 C12 1.380(7) . ?
C11 C10 1.379(7) . ?
C12 H12 0.9300 . ?
C10 H10 0.9300 . ?
C10 C9 1.379(7) . ?
C9 H9 0.9300 . ?
C7 H7 0.9300 . ?
C7 C1 1.468(7) . ?
C2 C3 1.391(7) . ?
C2 C1 1.399(7) . ?
C3 H3 0.9300 . ?
C3 C4 1.377(7) . ?
C5 H5 0.9300 . ?
C5 C4 1.385(7) . ?
C5 C6 1.379(7) . ?
C4 H4 0.9300 . ?
C1 C6 1.408(7) . ?
C6 H6 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
I1 I2 I3 178.419(16) . . ?
C8 N2 N1 124.2(4) . . ?
C8 N2 C12 122.4(4) . . ?
C12 N2 N1 113.4(4) . . ?
C7 N1 N2 115.4(4) . . ?
N2 C8 H8 120.3 . . ?
N2 C8 C9 119.4(5) . . ?
C9 C8 H8 120.3 . . ?
C12 C11 H11 120.3 . . ?
C12 C11 C10 119.4(5) . . ?
C10 C11 H11 120.3 . . ?
N2 C12 C11 118.9(5) . . ?
N2 C12 H12 120.6 . . ?
C11 C12 H12 120.6 . . ?
C11 C10 H10 120.0 . . ?
C9 C10 C11 120.1(5) . . ?
C9 C10 H10 120.0 . . ?
C8 C9 C10 119.7(5) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 H9 120.1 . . ?
N1 C7 H7 120.6 . . ?
N1 C7 C1 118.7(5) . . ?
C1 C7 H7 120.6 . . ?
C3 C2 Br1 117.7(4) . . ?
C3 C2 C1 121.3(5) . . ?
C1 C2 Br1 121.0(4) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 C2 119.2(5) . . ?
C4 C3 H3 120.4 . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C6 C5 C4 119.8(5) . . ?
C3 C4 C5 121.0(5) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C2 C1 C7 123.1(5) . . ?
C2 C1 C6 117.8(5) . . ?
C6 C1 C7 119.1(4) . . ?
C5 C6 C1 120.8(5) . . ?
C5 C6 H6 119.6 . . ?
C1 C6 H6 119.6 . . ?

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 C2 C3 C4 174.5(4) . . . . ?
Br1 C2 C1 C7 2.7(7) . . . . ?
Br1 C2 C1 C6 -175.4(4) . . . . ?
N2 N1 C7 C1 177.7(4) . . . . ?
N2 C8 C9 C10 -0.8(8) . . . . ?
N1 N2 C8 C9 -177.1(4) . . . . ?
N1 N2 C12 C11 176.7(4) . . . . ?
N1 C7 C1 C2 170.7(5) . . . . ?
N1 C7 C1 C6 -11.2(7) . . . . ?
C8 N2 N1 C7 35.6(7) . . . . ?
C8 N2 C12 C11 -4.7(7) . . . . ?
C11 C10 C9 C8 -2.4(8) . . . . ?
C12 N2 N1 C7 -145.9(4) . . . . ?
C12 N2 C8 C9 4.4(7) . . . . ?
C12 C11 C10 C9 2.1(8) . . . . ?
C10 C11 C12 N2 1.3(8) . . . . ?
C7 C1 C6 C5 -177.9(5) . . . . ?
C2 C3 C4 C5 1.7(8) . . . . ?
C2 C1 C6 C5 0.3(8) . . . . ?
C3 C2 C1 C7 -178.6(5) . . . . ?
C3 C2 C1 C6 3.3(8) . . . . ?
C4 C5 C6 C1 -2.8(8) . . . . ?
C1 C2 C3 C4 -4.3(8) . . . . ?
C6 C5 C4 C3 1.9(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 1.289
_oxdiff_exptl_absorpt_empirical_full_min 0.795
####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 2041343'
loop_
_audit_author_name
_audit_author_address
DHB
;NJXZC
China
;
_audit_update_record             
;
2021-08-25 deposited with the CCDC.	2021-09-01 downloaded from the CCDC.
;
_audit_creation_date             2021-08-24
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.09.11 svn.r3730fd0d for OlexSys, GUI svn.r6159)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'I3, C12 H10 Br N2'
_chemical_formula_sum            'C12 H10 Br I3 N2'
_chemical_formula_weight         642.83
_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'
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'

_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                   8.0318(12)
_cell_length_b                   11.7511(7)
_cell_length_c                   18.3130(12)
_cell_angle_alpha                104.739(6)
_cell_angle_beta                 93.199(10)
_cell_angle_gamma                91.627(9)
_cell_volume                     1667.3(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4736
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      29.1290
_cell_measurement_theta_min      2.3000
_shelx_estimated_absorpt_T_max   0.533
_shelx_estimated_absorpt_T_min   0.473
_exptl_absorpt_coefficient_mu    8.006
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.40469
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.561
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1160
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0567
_diffrn_reflns_av_unetI/netI     0.0946
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.831
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            13949
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.831
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.575
_diffrn_reflns_theta_min         2.305
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.831
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -59.00  38.00   1.00    8.00    --   11.74 -57.00  90.00   97
  2  ω    -16.00  79.00   1.00    8.00    --   11.74  77.00   0.00   95
  3  ω     36.00  62.00   1.00    8.00    --   11.74 178.00  60.00   26
  4  ω    -14.00  80.00   1.00    5.00    --   11.74  57.00-120.00   94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0001189000
_diffrn_orient_matrix_UB_12      -0.0387958000
_diffrn_orient_matrix_UB_13      -0.0366693000
_diffrn_orient_matrix_UB_21      -0.0083344000
_diffrn_orient_matrix_UB_22      0.0484072000
_diffrn_orient_matrix_UB_23      -0.0162761000
_diffrn_orient_matrix_UB_31      0.0881423000
_diffrn_orient_matrix_UB_32      0.0073972000
_diffrn_orient_matrix_UB_33      0.0011386000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6004
_reflns_number_total             7775
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         3.291
_refine_diff_density_min         -3.537
_refine_diff_density_rms         0.923
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         7775
_refine_ls_number_restraints     102
_refine_ls_R_factor_all          0.0841
_refine_ls_R_factor_gt           0.0788
_refine_ls_restrained_S_all      1.087
_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)+(0.1835P)²+807.3906P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.01844
_refine_ls_wR_factor_ref         0.1920
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C1) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(C3) \\sim Ueq, Uanis(C4) \\sim
Ueq, Uanis(C5) \\sim Ueq, Uanis(C6) \\sim Ueq: with sigma of 0.002 and sigma
for terminal atoms of 0.004
Uanis(N1) \\sim Ueq, Uanis(C9) \\sim Ueq: with sigma of 0.002 and sigma for
terminal atoms of 0.004
Uanis(C13) \\sim Ueq, Uanis(C14) \\sim Ueq, Uanis(C15) \\sim Ueq, Uanis(C17)
\\sim Ueq, Uanis(C18) \\sim Ueq, Uanis(C19) \\sim Ueq: with sigma of 0.002 and
sigma for terminal atoms of 0.004
Uanis(C21) \\sim Ueq, Uanis(C22) \\sim Ueq, Uanis(C23) \\sim Ueq: with sigma of
0.002 and sigma for terminal atoms of 0.004
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C11(H11),
 C12(H12), C14(H14), C15(H15), C16(H16), C18(H18), C19(H19), C20(H20), C21(H21),
  C22(H22), C23(H23), C24(H24)
;
_atom_sites_solution_hydrogens   geom
_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 0.2712(3) 0.3854(2) 0.57402(15) 0.0247(6) Uani 1 1 d . . . . .
I2 I 0.1645(3) 0.2025(2) 0.64647(14) 0.0213(6) Uani 1 1 d . . . . .
I3 I 0.0407(3) 0.0168(2) 0.71119(15) 0.0256(6) Uani 1 1 d . . . . .
I4 I 0.5579(3) 0.4512(2) 0.79209(15) 0.0256(6) Uani 1 1 d . . . . .
I5 I 0.6895(3) 0.2711(2) 0.86271(14) 0.0233(6) Uani 1 1 d . . . . .
I6 I 0.7992(4) 0.0926(2) 0.93788(16) 0.0290(6) Uani 1 1 d . . . . .
Br1 Br 0.3537(5) -0.1510(4) 0.8650(3) 0.0291(9) Uani 1 1 d . . . . .
N1 N 0.687(4) 0.125(3) 0.5678(19) 0.021(6) Uani 1 1 d . U . . .
N2 N 0.617(4) 0.017(3) 0.5834(17) 0.019(6) Uani 1 1 d . . . . .
C1 C 0.424(4) -0.172(3) 0.765(2) 0.015(6) Uani 1 1 d . U . . .
C2 C 0.405(5) -0.280(3) 0.712(2) 0.021(7) Uani 1 1 d . U . . .
H2 H 0.359862 -0.344407 0.726363 0.025 Uiso 1 1 calc R U . . .
C3 C 0.450(6) -0.293(4) 0.641(3) 0.032(9) Uani 1 1 d . U . . .
H3 H 0.438449 -0.365648 0.606026 0.038 Uiso 1 1 calc R U . . .
C4 C 0.518(5) -0.190(4) 0.620(2) 0.024(8) Uani 1 1 d . U . . .
H4 H 0.548811 -0.196710 0.571189 0.029 Uiso 1 1 calc R U . . .
C5 C 0.537(5) -0.085(4) 0.672(2) 0.023(8) Uani 1 1 d . U . . .
C6 C 0.489(4) -0.072(3) 0.746(2) 0.016(6) Uani 1 1 d . U . . .
H6 H 0.500341 0.000773 0.781585 0.019 Uiso 1 1 calc R U . . .
C7 C 0.614(5) 0.024(4) 0.654(2) 0.028(8) Uani 1 1 d . . . . .
H7 H 0.655514 0.090038 0.691861 0.033 Uiso 1 1 calc R U . . .
C8 C 0.658(5) 0.232(4) 0.611(3) 0.031(9) Uani 1 1 d . . . . .
H8 H 0.596767 0.240877 0.653506 0.037 Uiso 1 1 calc R U . . .
C9 C 0.722(5) 0.326(4) 0.590(2) 0.023(7) Uani 1 1 d . U . . .
H9 H 0.700170 0.401549 0.618176 0.028 Uiso 1 1 calc R U . . .
C10 C 0.821(5) 0.312(4) 0.527(2) 0.027(8) Uani 1 1 d . . . . .
H10 H 0.872202 0.377121 0.515692 0.032 Uiso 1 1 calc R U . . .
C11 C 0.839(6) 0.198(4) 0.484(2) 0.031(9) Uani 1 1 d . . . . .
H11 H 0.896369 0.185930 0.439620 0.037 Uiso 1 1 calc R U . . .
C12 C 0.773(5) 0.103(4) 0.505(2) 0.025(8) Uani 1 1 d . . . . .
H12 H 0.787983 0.026198 0.477791 0.030 Uiso 1 1 calc R U . . .
Br2 Br 0.8933(5) 0.6417(4) 0.6219(2) 0.0271(9) Uani 1 1 d . . . . .
N3 N 1.139(5) 0.474(3) 0.9185(19) 0.025(7) Uani 1 1 d . . . . .
N4 N 1.207(4) 0.369(3) 0.9326(17) 0.019(6) Uani 1 1 d . . . . .
C13 C 0.934(4) 0.652(3) 0.727(2) 0.018(7) Uani 1 1 d . U . . .
C14 C 0.874(5) 0.749(4) 0.777(2) 0.027(8) Uani 1 1 d . U . . .
H14 H 0.814478 0.806206 0.760702 0.032 Uiso 1 1 calc R U . . .
C15 C 0.913(5) 0.754(4) 0.856(2) 0.024(8) Uani 1 1 d . U . . .
H15 H 0.881015 0.819501 0.892213 0.029 Uiso 1 1 calc R U . . .
C16 C 0.993(6) 0.669(4) 0.880(2) 0.029(9) Uani 1 1 d . . . . .
H16 H 1.016555 0.675960 0.931712 0.034 Uiso 1 1 calc R U . . .
C17 C 1.037(4) 0.570(3) 0.826(2) 0.016(6) Uani 1 1 d . U . . .
C18 C 1.014(5) 0.559(3) 0.746(2) 0.022(7) Uani 1 1 d . U . . .
H18 H 1.049944 0.495138 0.710375 0.026 Uiso 1 1 calc R U . . .
C19 C 1.114(4) 0.471(3) 0.849(2) 0.018(7) Uani 1 1 d . U . . .
H19 H 1.145483 0.406110 0.811773 0.022 Uiso 1 1 calc R U . . .
C20 C 1.311(5) 0.392(3) 0.998(2) 0.022(8) Uani 1 1 d . . . . .
H20 H 1.333226 0.468279 1.026947 0.027 Uiso 1 1 calc R U . . .
C21 C 1.380(6) 0.301(4) 1.018(3) 0.032(9) Uani 1 1 d . U . . .
H21 H 1.449325 0.314582 1.061947 0.039 Uiso 1 1 calc R U . . .
C22 C 1.351(5) 0.193(4) 0.976(3) 0.030(9) Uani 1 1 d . U . . .
H22 H 1.402486 0.131248 0.991023 0.036 Uiso 1 1 calc R U . . .
C23 C 1.247(5) 0.168(4) 0.911(2) 0.026(8) Uani 1 1 d . U . . .
H23 H 1.228481 0.090742 0.882247 0.032 Uiso 1 1 calc R U . . .
C24 C 1.169(6) 0.260(4) 0.889(2) 0.029(9) Uani 1 1 d . . . . .
H24 H 1.094033 0.246653 0.846976 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
I1 I2 2.931(3) . ?
I2 I3 2.912(4) . ?
I4 I5 2.939(4) . ?
I5 I6 2.917(4) . ?
Br1 C1 1.90(3) . ?
N1 N2 1.47(4) . ?
N1 C8 1.34(5) . ?
N1 C12 1.34(5) . ?
N2 C7 1.29(5) . ?
C1 C2 1.39(5) . ?
C1 C6 1.40(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.35(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.46(6) . ?
C4 H4 0.9300 . ?
C4 C5 1.34(6) . ?
C5 C6 1.41(5) . ?
C5 C7 1.53(6) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C8 C9 1.36(6) . ?
C9 H9 0.9300 . ?
C9 C10 1.42(6) . ?
C10 H10 0.9300 . ?
C10 C11 1.39(6) . ?
C11 H11 0.9300 . ?
C11 C12 1.38(6) . ?
C12 H12 0.9300 . ?
Br2 C13 1.91(4) . ?
N3 N4 1.44(4) . ?
N3 C19 1.28(5) . ?
N4 C20 1.38(5) . ?
N4 C24 1.33(5) . ?
C13 C14 1.38(5) . ?
C13 C18 1.39(5) . ?
C14 H14 0.9300 . ?
C14 C15 1.46(6) . ?
C15 H15 0.9300 . ?
C15 C16 1.36(6) . ?
C16 H16 0.9300 . ?
C16 C17 1.39(5) . ?
C17 C18 1.43(5) . ?
C17 C19 1.47(5) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C20 C21 1.34(6) . ?
C21 H21 0.9300 . ?
C21 C22 1.31(6) . ?
C22 H22 0.9300 . ?
C22 C23 1.38(6) . ?
C23 H23 0.9300 . ?
C23 C24 1.40(6) . ?
C24 H24 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
I3 I2 I1 176.33(12) . . ?
I6 I5 I4 176.14(12) . . ?
C8 N1 N2 122(3) . . ?
C8 N1 C12 125(4) . . ?
C12 N1 N2 113(3) . . ?
C7 N2 N1 113(3) . . ?
C2 C1 Br1 121(3) . . ?
C2 C1 C6 121(3) . . ?
C6 C1 Br1 117(3) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 C1 121(4) . . ?
C3 C2 H2 119.6 . . ?
C2 C3 H3 120.7 . . ?
C2 C3 C4 119(4) . . ?
C4 C3 H3 120.7 . . ?
C3 C4 H4 119.9 . . ?
C5 C4 C3 120(4) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 C6 121(4) . . ?
C4 C5 C7 123(4) . . ?
C6 C5 C7 116(3) . . ?
C1 C6 C5 118(3) . . ?
C1 C6 H6 121.2 . . ?
C5 C6 H6 121.2 . . ?
N2 C7 C5 114(4) . . ?
N2 C7 H7 123.2 . . ?
C5 C7 H7 123.2 . . ?
N1 C8 H8 121.3 . . ?
N1 C8 C9 117(4) . . ?
C9 C8 H8 121.3 . . ?
C8 C9 H9 119.3 . . ?
C8 C9 C10 121(4) . . ?
C10 C9 H9 119.3 . . ?
C9 C10 H10 121.4 . . ?
C11 C10 C9 117(4) . . ?
C11 C10 H10 121.4 . . ?
C10 C11 H11 119.9 . . ?
C12 C11 C10 120(4) . . ?
C12 C11 H11 119.9 . . ?
N1 C12 C11 118(4) . . ?
N1 C12 H12 121.0 . . ?
C11 C12 H12 121.0 . . ?
C19 N3 N4 114(3) . . ?
C20 N4 N3 113(3) . . ?
C24 N4 N3 124(3) . . ?
C24 N4 C20 123(3) . . ?
C14 C13 Br2 116(3) . . ?
C14 C13 C18 126(4) . . ?
C18 C13 Br2 117(3) . . ?
C13 C14 H14 123.0 . . ?
C13 C14 C15 114(4) . . ?
C15 C14 H14 123.0 . . ?
C14 C15 H15 118.1 . . ?
C16 C15 C14 124(4) . . ?
C16 C15 H15 118.1 . . ?
C15 C16 H16 121.0 . . ?
C15 C16 C17 118(4) . . ?
C17 C16 H16 121.0 . . ?
C16 C17 C18 123(4) . . ?
C16 C17 C19 121(3) . . ?
C18 C17 C19 116(3) . . ?
C13 C18 C17 115(3) . . ?
C13 C18 H18 122.5 . . ?
C17 C18 H18 122.5 . . ?
N3 C19 C17 120(3) . . ?
N3 C19 H19 120.0 . . ?
C17 C19 H19 120.0 . . ?
N4 C20 H20 120.8 . . ?
C21 C20 N4 118(4) . . ?
C21 C20 H20 120.8 . . ?
C20 C21 H21 119.5 . . ?
C22 C21 C20 121(4) . . ?
C22 C21 H21 119.5 . . ?
C21 C22 H22 119.3 . . ?
C21 C22 C23 121(5) . . ?
C23 C22 H22 119.3 . . ?
C22 C23 H23 120.3 . . ?
C22 C23 C24 119(4) . . ?
C24 C23 H23 120.3 . . ?
N4 C24 C23 116(4) . . ?
N4 C24 H24 121.9 . . ?
C23 C24 H24 121.9 . . ?

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 C1 C2 C3 178(3) . . . . ?
Br1 C1 C6 C5 -178(3) . . . . ?
N1 N2 C7 C5 178(3) . . . . ?
N1 C8 C9 C10 -3(6) . . . . ?
N2 N1 C8 C9 -177(3) . . . . ?
N2 N1 C12 C11 177(3) . . . . ?
C1 C2 C3 C4 -1(6) . . . . ?
C2 C1 C6 C5 -1(5) . . . . ?
C2 C3 C4 C5 1(6) . . . . ?
C3 C4 C5 C6 -1(6) . . . . ?
C3 C4 C5 C7 177(4) . . . . ?
C4 C5 C6 C1 1(6) . . . . ?
C4 C5 C7 N2 18(6) . . . . ?
C6 C1 C2 C3 1(6) . . . . ?
C6 C5 C7 N2 -164(4) . . . . ?
C7 C5 C6 C1 -177(3) . . . . ?
C8 N1 N2 C7 -37(5) . . . . ?
C8 N1 C12 C11 0(6) . . . . ?
C8 C9 C10 C11 5(6) . . . . ?
C9 C10 C11 C12 -5(6) . . . . ?
C10 C11 C12 N1 2(6) . . . . ?
C12 N1 N2 C7 146(4) . . . . ?
C12 N1 C8 C9 0(6) . . . . ?
Br2 C13 C14 C15 -178(3) . . . . ?
Br2 C13 C18 C17 -178(3) . . . . ?
N3 N4 C20 C21 179(4) . . . . ?
N3 N4 C24 C23 180(4) . . . . ?
N4 N3 C19 C17 177(3) . . . . ?
N4 C20 C21 C22 1(7) . . . . ?
C13 C14 C15 C16 -3(6) . . . . ?
C14 C13 C18 C17 -1(6) . . . . ?
C14 C15 C16 C17 -1(6) . . . . ?
C15 C16 C17 C18 5(6) . . . . ?
C15 C16 C17 C19 -176(4) . . . . ?
C16 C17 C18 C13 -4(5) . . . . ?
C16 C17 C19 N3 1(6) . . . . ?
C18 C13 C14 C15 5(6) . . . . ?
C18 C17 C19 N3 -180(4) . . . . ?
C19 N3 N4 C20 147(4) . . . . ?
C19 N3 N4 C24 -35(5) . . . . ?
C19 C17 C18 C13 177(3) . . . . ?
C20 N4 C24 C23 -3(6) . . . . ?
C20 C21 C22 C23 -1(7) . . . . ?
C21 C22 C23 C24 -1(7) . . . . ?
C22 C23 C24 N4 3(6) . . . . ?
C24 N4 C20 C21 1(6) . . . . ?

_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.226
_oxdiff_exptl_absorpt_empirical_full_min 0.563
####################################################################### 
# 
# 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_d1
_database_code_depnum_ccdc_archive 'CCDC 2041339'
loop_
_audit_author_name
_audit_author_address
Duan
;Nanjingxiaozhuang university
China
;
_audit_update_record             
;
2020-10-29 deposited with the CCDC.	2021-09-01 downloaded from the CCDC.
;
_audit_creation_date             2019-09-20
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r5938)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'I3, C12 H10 Cl N2'
_chemical_formula_sum            'C12 H10 Cl I3 N2'
_chemical_formula_weight         598.37
_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'
Cl Cl 0.1484 0.1585 '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'

_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                   12.8734(5)
_cell_length_b                   14.7359(6)
_cell_length_c                   8.5326(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.977(3)
_cell_angle_gamma                90
_cell_volume                     1617.68(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3505
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      29.2800
_cell_measurement_theta_min      2.7360
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    5.947
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83535
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    2.457
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_av_unetI/netI     0.0423
_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       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            6509
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.101
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -10.00  27.00   1.00    1.50    --  -11.59 -99.00 -30.00   37
  2  ω     44.00  71.00   1.00    1.50    --   11.74-178.00 120.00   27
  3  ω    -85.00  11.00   1.00    1.50    --  -11.59 -37.00  90.00   96
  4  ω    -92.00 -69.00   1.00    1.50    --  -11.59 -19.00-150.00   23
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0106379000
_diffrn_orient_matrix_UB_12      -0.0181686000
_diffrn_orient_matrix_UB_13      -0.0748337000
_diffrn_orient_matrix_UB_21      -0.0525115000
_diffrn_orient_matrix_UB_22      -0.0140540000
_diffrn_orient_matrix_UB_23      -0.0093734000
_diffrn_orient_matrix_UB_31      -0.0129183000
_diffrn_orient_matrix_UB_32      0.0422665000
_diffrn_orient_matrix_UB_33      -0.0352507000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2505
_reflns_number_total             2850
_reflns_odcompleteness_completeness 99.62
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS n/a (Sheldrick, 2008)'
_refine_diff_density_max         0.550
_refine_diff_density_min         -0.732
_refine_diff_density_rms         0.142
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2850
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0304
_refine_ls_R_factor_gt           0.0243
_refine_ls_restrained_S_all      1.039
_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)+(0.0039P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0414
_refine_ls_wR_factor_ref         0.0449
_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:
 C6(H6), C3(H3), C4(H4), C5(H5), C2(H2), C1(H1), C11(H11), C12(H12), C9(H9),
 C10(H10)
;
_atom_sites_solution_hydrogens   geom
_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
I2 I 0.56957(2) 0.32113(2) 1.02772(3) 0.01432(8) Uani 1 1 d . . . . .
I3 I 0.77283(2) 0.28434(2) 1.17107(3) 0.01639(9) Uani 1 1 d . . . . .
I1 I 0.36040(2) 0.35866(2) 0.89167(3) 0.01844(9) Uani 1 1 d . . . . .
Cl1 Cl -0.02897(9) 0.69336(8) 0.61092(13) 0.0220(3) Uani 1 1 d . . . . .
N2 N 0.1900(3) 0.4678(2) 0.6122(4) 0.0126(8) Uani 1 1 d . . . . .
N1 N 0.2753(3) 0.4787(2) 0.5115(4) 0.0142(8) Uani 1 1 d . . . . .
C6 C 0.1211(3) 0.5308(3) 0.6037(4) 0.0141(10) Uani 1 1 d . . . . .
H6 H 0.129125 0.580716 0.538562 0.017 Uiso 1 1 calc R U . . .
C3 C 0.4336(3) 0.4834(3) 0.3091(4) 0.0169(10) Uani 1 1 d . . . . .
H3 H 0.485968 0.485208 0.236755 0.020 Uiso 1 1 calc R U . . .
C4 C 0.3931(3) 0.4018(3) 0.3532(4) 0.0153(10) Uani 1 1 d . . . . .
H4 H 0.419160 0.347978 0.313266 0.018 Uiso 1 1 calc R U . . .
C5 C 0.3132(3) 0.3999(3) 0.4576(4) 0.0146(10) Uani 1 1 d . . . . .
H5 H 0.285936 0.344831 0.490106 0.018 Uiso 1 1 calc R U . . .
C2 C 0.3965(3) 0.5636(3) 0.3723(4) 0.0163(10) Uani 1 1 d . . . . .
H2 H 0.424879 0.619194 0.344759 0.020 Uiso 1 1 calc R U . . .
C1 C 0.3173(3) 0.5596(3) 0.4762(5) 0.0151(10) Uani 1 1 d . . . . .
H1 H 0.292794 0.612406 0.521817 0.018 Uiso 1 1 calc R U . . .
C7 C 0.0297(3) 0.5217(3) 0.6997(4) 0.0137(10) Uani 1 1 d . . . . .
C11 C -0.0767(3) 0.4291(3) 0.8661(5) 0.0176(10) Uani 1 1 d . . . . .
H11 H -0.089301 0.373895 0.914676 0.021 Uiso 1 1 calc R U . . .
C12 C 0.0104(3) 0.4402(3) 0.7768(5) 0.0167(10) Uani 1 1 d . . . . .
H12 H 0.056884 0.392315 0.768194 0.020 Uiso 1 1 calc R U . . .
C8 C -0.0423(3) 0.5916(3) 0.7139(5) 0.0146(10) Uani 1 1 d . . . . .
C9 C -0.1284(3) 0.5822(3) 0.8082(5) 0.0194(10) Uani 1 1 d . . . . .
H9 H -0.173957 0.630420 0.820523 0.023 Uiso 1 1 calc R U . . .
C10 C -0.1449(3) 0.5012(3) 0.8822(5) 0.0194(11) Uani 1 1 d . . . . .
H10 H -0.202487 0.494402 0.943938 0.023 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
I2 I3 2.9011(4) . ?
I2 I1 2.9475(4) . ?
Cl1 C8 1.749(4) . ?
N2 N1 1.426(4) . ?
N2 C6 1.283(5) . ?
N1 C5 1.347(5) . ?
N1 C1 1.347(5) . ?
C6 H6 0.9300 . ?
C6 C7 1.463(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.368(6) . ?
C3 C2 1.391(6) . ?
C4 H4 0.9300 . ?
C4 C5 1.385(5) . ?
C5 H5 0.9300 . ?
C2 H2 0.9300 . ?
C2 C1 1.376(5) . ?
C1 H1 0.9300 . ?
C7 C12 1.396(6) . ?
C7 C8 1.394(6) . ?
C11 H11 0.9300 . ?
C11 C12 1.386(6) . ?
C11 C10 1.387(6) . ?
C12 H12 0.9300 . ?
C8 C9 1.398(6) . ?
C9 H9 0.9300 . ?
C9 C10 1.371(6) . ?
C10 H10 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
I3 I2 I1 178.257(12) . . ?
C6 N2 N1 115.5(3) . . ?
C5 N1 N2 113.9(3) . . ?
C5 N1 C1 122.3(4) . . ?
C1 N1 N2 123.8(3) . . ?
N2 C6 H6 121.0 . . ?
N2 C6 C7 118.0(4) . . ?
C7 C6 H6 121.0 . . ?
C4 C3 H3 120.0 . . ?
C4 C3 C2 120.1(4) . . ?
C2 C3 H3 120.0 . . ?
C3 C4 H4 120.2 . . ?
C3 C4 C5 119.5(4) . . ?
C5 C4 H4 120.2 . . ?
N1 C5 C4 119.2(4) . . ?
N1 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?
C3 C2 H2 120.5 . . ?
C1 C2 C3 119.0(4) . . ?
C1 C2 H2 120.5 . . ?
N1 C1 C2 119.6(4) . . ?
N1 C1 H1 120.2 . . ?
C2 C1 H1 120.2 . . ?
C12 C7 C6 120.2(4) . . ?
C8 C7 C6 122.1(4) . . ?
C8 C7 C12 117.7(4) . . ?
C12 C11 H11 120.3 . . ?
C12 C11 C10 119.4(4) . . ?
C10 C11 H11 120.3 . . ?
C7 C12 H12 119.3 . . ?
C11 C12 C7 121.4(4) . . ?
C11 C12 H12 119.3 . . ?
C7 C8 Cl1 120.8(3) . . ?
C7 C8 C9 121.3(4) . . ?
C9 C8 Cl1 117.9(3) . . ?
C8 C9 H9 120.3 . . ?
C10 C9 C8 119.3(4) . . ?
C10 C9 H9 120.3 . . ?
C11 C10 H10 119.6 . . ?
C9 C10 C11 120.8(4) . . ?
C9 C10 H10 119.6 . . ?

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
Cl1 C8 C9 C10 175.7(3) . . . . ?
N2 N1 C5 C4 177.2(3) . . . . ?
N2 N1 C1 C2 -177.1(4) . . . . ?
N2 C6 C7 C12 -10.4(6) . . . . ?
N2 C6 C7 C8 171.6(4) . . . . ?
N1 N2 C6 C7 177.7(3) . . . . ?
C6 N2 N1 C5 -146.4(4) . . . . ?
C6 N2 N1 C1 35.6(5) . . . . ?
C6 C7 C12 C11 -178.8(4) . . . . ?
C6 C7 C8 Cl1 2.3(6) . . . . ?
C6 C7 C8 C9 -179.0(4) . . . . ?
C3 C4 C5 N1 1.3(6) . . . . ?
C3 C2 C1 N1 -1.8(6) . . . . ?
C4 C3 C2 C1 -1.6(6) . . . . ?
C5 N1 C1 C2 5.0(6) . . . . ?
C2 C3 C4 C5 1.8(6) . . . . ?
C1 N1 C5 C4 -4.8(6) . . . . ?
C7 C8 C9 C10 -3.1(6) . . . . ?
C12 C7 C8 Cl1 -175.7(3) . . . . ?
C12 C7 C8 C9 3.0(6) . . . . ?
C12 C11 C10 C9 1.5(6) . . . . ?
C8 C7 C12 C11 -0.7(6) . . . . ?
C8 C9 C10 C11 0.8(6) . . . . ?
C10 C11 C12 C7 -1.5(6) . . . . ?

_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 1.308
_oxdiff_exptl_absorpt_empirical_full_min 0.838
####################################################################### 
# 
# 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_d2_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2041428'
loop_
_audit_author_name
_audit_author_address
Duan
;Nanjingxiaozhuang university
China
;
_audit_update_record             
;
2020-10-30 deposited with the CCDC.	2021-09-01 downloaded from the CCDC.
;
_audit_creation_date             2018-11-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(I1.5), C12 H10 I N2'
_chemical_formula_sum            'C12 H10 I4 N2'
_chemical_formula_weight         689.82
_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'
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'

_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                   9.2552(5)
_cell_length_b                   9.4866(7)
_cell_length_c                   11.8244(10)
_cell_angle_alpha                67.613(7)
_cell_angle_beta                 79.570(6)
_cell_angle_gamma                61.575(7)
_cell_volume                     844.21(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5505
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      29.2760
_cell_measurement_theta_min      2.5040
_shelx_estimated_absorpt_T_max   0.590
_shelx_estimated_absorpt_T_min   0.472
_exptl_absorpt_coefficient_mu    7.369
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62971
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    2.714
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0381
_diffrn_reflns_av_unetI/netI     0.0418
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9524
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         1.863
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -40.00  62.00   1.00    1.00    --  -11.59  57.00-180.00  102
  2  ω    -88.00  21.00   1.00    1.00    --  -11.59 -77.00 -90.00  109
  3  ω    -85.00  17.00   1.00    1.00    --  -11.59 -57.00  30.00  102
  4  ω    -86.00 -47.00   1.00    1.00    --  -11.59 -37.00 120.00   39
  5  ω    -20.00  53.00   1.00    1.00    --   11.74 -99.00 -30.00   73
  6  ω     35.00 101.00   1.00    1.00    --   11.74 178.00 150.00   66
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0244004000
_diffrn_orient_matrix_UB_12      0.0593423000
_diffrn_orient_matrix_UB_13      -0.0454095000
_diffrn_orient_matrix_UB_21      0.0033282000
_diffrn_orient_matrix_UB_22      0.0310550000
_diffrn_orient_matrix_UB_23      0.0448866000
_diffrn_orient_matrix_UB_31      0.0835925000
_diffrn_orient_matrix_UB_32      -0.0607586000
_diffrn_orient_matrix_UB_33      0.0114895000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2686
_reflns_number_total             2966
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.786
_refine_diff_density_min         -0.831
_refine_diff_density_rms         0.144
_refine_ls_extinction_coef       0.00134(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         2966
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0270
_refine_ls_R_factor_gt           0.0233
_refine_ls_restrained_S_all      1.007
_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)+(0.0078P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0403
_refine_ls_wR_factor_ref         0.0422
_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:
 C6(H6), C8(H8), C5(H5), C10(H10), C1(H1), C2(H2), C11(H11), C12(H12), C3(H3),
 C4(H4)
;
_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
I3 I 0.500000 1.500000 0.000000 0.01525(11) Uani 1 2 d S T P . .
I5 I 0.500000 0.000000 0.500000 0.01718(11) Uani 1 2 d S T P . .
I4 I 0.59327(3) 0.27649(4) 0.39794(3) 0.01991(9) Uani 1 1 d . . . . .
I2 I 0.24367(3) 1.45430(4) -0.07139(3) 0.02055(9) Uani 1 1 d . . . . .
I1 I 0.74239(4) 1.01703(4) 0.13757(3) 0.02260(10) Uani 1 1 d . . . . .
N1 N 0.8545(4) 0.1639(4) 0.6470(3) 0.0157(8) Uani 1 1 d . . . . .
N2 N 0.9354(4) 0.2457(4) 0.5525(3) 0.0173(9) Uani 1 1 d . . . . .
C7 C 0.9190(5) 0.4936(5) 0.3873(4) 0.0148(10) Uani 1 1 d . . . . .
C6 C 0.8479(5) 0.4025(5) 0.4907(4) 0.0150(10) Uani 1 1 d . . . . .
H6 H 0.738749 0.458314 0.512004 0.018 Uiso 1 1 calc R . . . .
C9 C 0.8857(5) 0.7554(5) 0.2267(4) 0.0157(10) Uani 1 1 d . . . . .
C8 C 0.8225(5) 0.6660(6) 0.3257(4) 0.0170(10) Uani 1 1 d . . . . .
H8 H 0.715419 0.720824 0.351331 0.020 Uiso 1 1 calc R . . . .
C5 C 0.9347(5) -0.0073(5) 0.6845(4) 0.0201(11) Uani 1 1 d . . . . .
H5 H 1.035818 -0.060631 0.650112 0.024 Uiso 1 1 calc R . . . .
C10 C 1.0441(5) 0.6737(6) 0.1863(4) 0.0210(11) Uani 1 1 d . . . . .
H10 H 1.084996 0.733447 0.117763 0.025 Uiso 1 1 calc R . . . .
C1 C 0.7097(5) 0.2425(6) 0.6988(4) 0.0220(11) Uani 1 1 d . . . . .
H1 H 0.656928 0.360879 0.674223 0.026 Uiso 1 1 calc R . . . .
C2 C 0.6406(5) 0.1510(6) 0.7860(4) 0.0246(12) Uani 1 1 d . . . . .
H2 H 0.540503 0.206337 0.820572 0.029 Uiso 1 1 calc R . . . .
C11 C 1.1412(5) 0.5026(6) 0.2483(4) 0.0223(11) Uani 1 1 d . . . . .
H11 H 1.247679 0.448127 0.221573 0.027 Uiso 1 1 calc R . . . .
C12 C 1.0811(5) 0.4128(6) 0.3493(4) 0.0183(10) Uani 1 1 d . . . . .
H12 H 1.147829 0.298992 0.392048 0.022 Uiso 1 1 calc R . . . .
C3 C 0.7193(6) -0.0245(6) 0.8232(4) 0.0240(11) Uani 1 1 d . . . . .
H3 H 0.672101 -0.088812 0.881730 0.029 Uiso 1 1 calc R . . . .
C4 C 0.8690(6) -0.1029(6) 0.7723(4) 0.0257(12) Uani 1 1 d . . . . .
H4 H 0.925289 -0.221220 0.797885 0.031 Uiso 1 1 calc R . . . .


_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
I3 I2 2.9175(3) . ?
I3 I2 2.9175(3) 2_685 ?
I5 I4 2.9067(4) 2_656 ?
I5 I4 2.9067(4) . ?
I1 C9 2.100(4) . ?
N1 N2 1.415(5) . ?
N1 C5 1.344(5) . ?
N1 C1 1.351(5) . ?
N2 C6 1.282(5) . ?
C7 C6 1.456(6) . ?
C7 C8 1.393(6) . ?
C7 C12 1.402(5) . ?
C9 C8 1.378(6) . ?
C9 C10 1.388(6) . ?
C5 C4 1.360(6) . ?
C10 C11 1.387(6) . ?
C1 C2 1.354(6) . ?
C2 C3 1.378(6) . ?
C11 C12 1.377(6) . ?
C3 C4 1.376(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
I2 I3 I2 180.0 . 2_685 ?
I4 I5 I4 180.0 2_656 . ?
C5 N1 N2 113.9(3) . . ?
C5 N1 C1 120.2(4) . . ?
C1 N1 N2 125.9(3) . . ?
C6 N2 N1 116.6(3) . . ?
C8 C7 C6 118.6(4) . . ?
C8 C7 C12 119.6(4) . . ?
C12 C7 C6 121.8(4) . . ?
N2 C6 C7 120.2(4) . . ?
C8 C9 I1 119.9(3) . . ?
C8 C9 C10 120.3(4) . . ?
C10 C9 I1 119.8(3) . . ?
C9 C8 C7 120.0(4) . . ?
N1 C5 C4 120.4(4) . . ?
C11 C10 C9 119.8(4) . . ?
N1 C1 C2 120.8(4) . . ?
C1 C2 C3 119.7(4) . . ?
C12 C11 C10 120.5(4) . . ?
C11 C12 C7 119.7(4) . . ?
C4 C3 C2 118.8(4) . . ?
C5 C4 C3 120.0(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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.790
_oxdiff_exptl_absorpt_empirical_full_min 0.736
####################################################################### 
# 
# 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_11
_database_code_depnum_ccdc_archive 'CCDC 2041342'
loop_
_audit_author_name
_audit_author_address
Duan
;Nanjingxiaozhuang university
China
;
_audit_update_record             
;
2020-10-29 deposited with the CCDC.	2021-09-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H10 Cl I3 N2'
_chemical_formula_weight         598.37

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'
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'

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   7.4762(5)
_cell_length_b                   8.8528(7)
_cell_length_c                   25.417(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.563(6)
_cell_angle_gamma                90.00
_cell_volume                     1628.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    8230
_cell_measurement_theta_max      29.2850
_cell_measurement_theta_min      2.350

_exptl_crystal_description       needel
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.441
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1088
_exptl_absorpt_coefficient_mu    5.909
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3845
_exptl_absorpt_correction_T_max  0.7566
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9808
_diffrn_reflns_av_R_equivalents  0.1017
_diffrn_reflns_av_sigmaI/netI    0.1144
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.83
_diffrn_reflns_theta_max         28.69
_reflns_number_total             3776
_reflns_number_gt                2336
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0877P)²+7.8868P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3776
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1240
_refine_ls_R_factor_gt           0.0783
_refine_ls_wR_factor_ref         0.2244
_refine_ls_wR_factor_gt          0.1812
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.4164(6) 0.6752(5) 0.52947(15) 0.0437(10) Uani 1 1 d . . .
N1 N 0.4303(13) 0.6086(12) 0.7984(4) 0.024(2) Uani 1 1 d . . .
N2 N 0.3925(14) 0.6123(12) 0.7387(4) 0.024(2) Uani 1 1 d . . .
C1 C 0.1616(19) 0.3640(15) 0.6309(6) 0.031(3) Uani 1 1 d . . .
H1 H 0.1109 0.2991 0.6520 0.037 Uiso 1 1 calc R . .
C2 C 0.1206(19) 0.3450(15) 0.5753(6) 0.033(3) Uani 1 1 d . . .
H2 H 0.0405 0.2690 0.5585 0.039 Uiso 1 1 calc R . .
C3 C 0.2042(19) 0.4448(15) 0.5441(7) 0.035(3) Uani 1 1 d . . .
H3 H 0.1804 0.4331 0.5066 0.042 Uiso 1 1 calc R . .
C4 C 0.3196(18) 0.5579(15) 0.5697(6) 0.030(3) Uani 1 1 d . . .
C5 C 0.3612(16) 0.5747(15) 0.6242(4) 0.023(3) Uani 1 1 d . . .
H5 H 0.4442 0.6487 0.6411 0.027 Uiso 1 1 calc R . .
C6 C 0.2777(18) 0.4790(15) 0.6553(5) 0.028(3) Uani 1 1 d . . .
C7 C 0.3205(17) 0.4943(16) 0.7157(6) 0.031(3) Uani 1 1 d . . .
H7 H 0.2933 0.4151 0.7365 0.037 Uiso 1 1 calc R . .
C8 C 0.3516(17) 0.7174(14) 0.8219(5) 0.024(3) Uani 1 1 d . . .
H8 H 0.2743 0.7884 0.8006 0.029 Uiso 1 1 calc R . .
C9 C 0.386(2) 0.7228(15) 0.8764(6) 0.032(3) Uani 1 1 d . . .
H9 H 0.3326 0.7977 0.8933 0.039 Uiso 1 1 calc R . .
C10 C 0.499(2) 0.6163(19) 0.9068(6) 0.043(4) Uani 1 1 d . . .
H10 H 0.5218 0.6177 0.9445 0.051 Uiso 1 1 calc R . .
C11 C 0.582(2) 0.5056(15) 0.8816(5) 0.033(3) Uani 1 1 d . . .
H11 H 0.6632 0.4358 0.9021 0.040 Uiso 1 1 calc R . .
C12 C 0.5405(18) 0.5022(14) 0.8263(6) 0.028(3) Uani 1 1 d . . .
H12 H 0.5884 0.4268 0.8084 0.034 Uiso 1 1 calc R . .
I1 I 0.11391(11) 0.08216(11) 0.75336(3) 0.0288(3) Uani 1 1 d . . .
I2 I 0.11938(11) 0.25471(10) 0.85381(3) 0.0267(3) Uani 1 1 d . . .
I3 I 0.11138(13) 0.42347(11) 0.94959(4) 0.0344(3) 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
Cl1 C4 1.737(14) . ?
N1 C12 1.332(16) . ?
N1 C8 1.344(15) . ?
N1 N2 1.473(14) . ?
N2 C7 1.250(17) . ?
C1 C2 1.38(2) . ?
C1 C6 1.380(19) . ?
C1 H1 0.9300 . ?
C2 C3 1.432(19) . ?
C2 H2 0.9300 . ?
C3 C4 1.374(19) . ?
C3 H3 0.9300 . ?
C4 C5 1.351(17) . ?
C5 C6 1.405(17) . ?
C5 H5 0.9300 . ?
C6 C7 1.496(19) . ?
C7 H7 0.9300 . ?
C8 C9 1.347(18) . ?
C8 H8 0.9300 . ?
C9 C10 1.37(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.40(2) . ?
C10 H10 0.9300 . ?
C11 C12 1.361(19) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
I1 I2 2.9668(11) . ?
I2 I3 2.8698(12) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 N1 C8 123.5(12) . . ?
C12 N1 N2 119.9(10) . . ?
C8 N1 N2 116.7(10) . . ?
C7 N2 N1 114.2(11) . . ?
C2 C1 C6 120.2(13) . . ?
C2 C1 H1 119.9 . . ?
C6 C1 H1 119.9 . . ?
C1 C2 C3 118.5(13) . . ?
C1 C2 H2 120.8 . . ?
C3 C2 H2 120.8 . . ?
C4 C3 C2 119.8(14) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C5 C4 C3 121.4(13) . . ?
C5 C4 Cl1 121.1(10) . . ?
C3 C4 Cl1 117.5(11) . . ?
C4 C5 C6 119.3(12) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C1 C6 C5 120.7(12) . . ?
C1 C6 C7 118.4(12) . . ?
C5 C6 C7 120.8(12) . . ?
N2 C7 C6 120.7(12) . . ?
N2 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
N1 C8 C9 119.5(12) . . ?
N1 C8 H8 120.3 . . ?
C9 C8 H8 120.3 . . ?
C8 C9 C10 119.0(13) . . ?
C8 C9 H9 120.5 . . ?
C10 C9 H9 120.5 . . ?
C9 C10 C11 120.5(13) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C12 C11 C10 118.5(14) . . ?
C12 C11 H11 120.7 . . ?
C10 C11 H11 120.7 . . ?
N1 C12 C11 118.9(13) . . ?
N1 C12 H12 120.5 . . ?
C11 C12 H12 120.5 . . ?
I3 I2 I1 178.04(4) . . ?

_diffrn_measured_fraction_theta_max 0.901
_diffrn_reflns_theta_full        28.69
_diffrn_measured_fraction_theta_full 0.901
_refine_diff_density_max         2.194
_refine_diff_density_min         -2.251
_refine_diff_density_rms         0.378
####################################################################### 
# 
# 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_01-3
_database_code_depnum_ccdc_archive 'CCDC 2041341'
loop_
_audit_author_name
_audit_author_address
DHB
;NJXZC
China
;
_audit_update_record             
;
2021-08-25 deposited with the CCDC.	2021-09-01 downloaded from the CCDC.
;
_audit_creation_date             2021-08-24
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.09.11 svn.r3730fd0d for OlexSys, GUI svn.r6159)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'I3, C12 H10 F N2'
_chemical_formula_sum            'C12 H10 F I3 N2'
_chemical_formula_weight         581.92
_chemical_absolute_configuration ?
_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'
F F 0.0171 0.0103 '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'

_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           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
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                   7.1679(3)
_cell_length_b                   10.8199(4)
_cell_length_c                   20.5129(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1590.90(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7153
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      29.0480
_cell_measurement_theta_min      2.7190
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    5.890
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69035
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            black
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    2.430
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_av_unetI/netI     0.0335
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            10991
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         2.128
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -31.00  62.00   1.00    1.30    --  -11.59  57.00   0.00   93
  2  ω    -87.00  16.00   1.00    1.30    --  -11.59 -77.00-120.00  103
  3  ω    -16.00  86.00   1.00    1.30    --   11.74  77.00 120.00  102
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0005657000
_diffrn_orient_matrix_UB_12      -0.0310353000
_diffrn_orient_matrix_UB_13      -0.0304665000
_diffrn_orient_matrix_UB_21      -0.0860516000
_diffrn_orient_matrix_UB_22      -0.0283867000
_diffrn_orient_matrix_UB_23      0.0082021000
_diffrn_orient_matrix_UB_31      -0.0487959000
_diffrn_orient_matrix_UB_32      0.0503433000
_diffrn_orient_matrix_UB_33      -0.0141179000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.713
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                2752
_reflns_number_total             2819
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.785
_refine_diff_density_min         -0.568
_refine_diff_density_rms         0.107
_refine_ls_abs_structure_details 
;
 Flack x determined using 1110 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2819
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0219
_refine_ls_R_factor_gt           0.0209
_refine_ls_restrained_S_all      1.039
_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)+(0.0157P)²+0.5240P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0420
_refine_ls_wR_factor_ref         0.0425
_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:
 C2(H2), C4(H4), C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C11(H11),
 C12(H12)
;
_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
I1 I 0.83706(5) 0.60700(4) 0.18503(2) 0.02123(12) Uani 1 1 d . . . . .
I2 I 0.77916(5) 0.75733(3) 0.30181(2) 0.01496(10) Uani 1 1 d . . . . .
I3 I 0.71907(6) 0.91680(4) 0.41356(2) 0.02396(12) Uani 1 1 d . . . . .
F1 F 0.8717(5) 0.5841(4) 0.4482(2) 0.0367(11) Uani 1 1 d . . . . .
N1 N 0.7215(7) 0.1951(4) 0.2139(3) 0.0156(12) Uani 1 1 d . . . . .
N2 N 0.7340(7) 0.2755(5) 0.2687(3) 0.0179(12) Uani 1 1 d . . . . .
C1 C 0.6640(8) 0.3083(6) 0.3802(3) 0.0165(14) Uani 1 1 d . . . . .
C2 C 0.7676(8) 0.4165(5) 0.3846(3) 0.0179(14) Uani 1 1 d . . . . .
H2 H 0.834481 0.445703 0.348879 0.021 Uiso 1 1 calc R U . . .
C3 C 0.7692(9) 0.4793(5) 0.4426(3) 0.0195(15) Uani 1 1 d . . . . .
C4 C 0.6718(8) 0.4399(6) 0.4976(4) 0.0247(16) Uani 1 1 d . . . . .
H4 H 0.675780 0.484556 0.536365 0.030 Uiso 1 1 calc R U . . .
C5 C 0.5685(9) 0.3315(6) 0.4926(4) 0.0240(17) Uani 1 1 d . . . . .
H5 H 0.501404 0.303074 0.528367 0.029 Uiso 1 1 calc R U . . .
C6 C 0.5644(9) 0.2656(6) 0.4350(3) 0.0214(15) Uani 1 1 d . . . . .
H6 H 0.495843 0.192797 0.432372 0.026 Uiso 1 1 calc R U . . .
C7 C 0.6549(7) 0.2358(6) 0.3204(3) 0.0166(14) Uani 1 1 d . . . . .
H7 H 0.591542 0.160764 0.319906 0.020 Uiso 1 1 calc R U . . .
C8 C 0.7343(8) 0.0706(5) 0.2182(3) 0.0181(14) Uani 1 1 d . . . . .
H8 H 0.746156 0.032809 0.258712 0.022 Uiso 1 1 calc R U . . .
C9 C 0.7296(9) 0.0004(6) 0.1625(3) 0.0212(15) Uani 1 1 d . . . . .
H9 H 0.736311 -0.085249 0.165083 0.025 Uiso 1 1 calc R U . . .
C10 C 0.7150(9) 0.0574(6) 0.1028(3) 0.0189(15) Uani 1 1 d . . . . .
H10 H 0.710916 0.010407 0.064865 0.023 Uiso 1 1 calc R U . . .
C11 C 0.7063(9) 0.1848(6) 0.0995(3) 0.0216(15) Uani 1 1 d . . . . .
H11 H 0.697523 0.224006 0.059248 0.026 Uiso 1 1 calc R U . . .
C12 C 0.7106(8) 0.2535(6) 0.1559(3) 0.0181(14) Uani 1 1 d . . . . .
H12 H 0.705979 0.339366 0.154042 0.022 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
I1 I2 2.9251(6) . ?
I2 I3 2.9014(6) . ?
F1 C3 1.356(7) . ?
N1 N2 1.425(7) . ?
N1 C8 1.353(8) . ?
N1 C12 1.350(8) . ?
N2 C7 1.277(8) . ?
C1 C2 1.389(8) . ?
C1 C6 1.410(9) . ?
C1 C7 1.458(9) . ?
C2 H2 0.9300 . ?
C2 C3 1.370(9) . ?
C3 C4 1.395(9) . ?
C4 H4 0.9300 . ?
C4 C5 1.392(9) . ?
C5 H5 0.9300 . ?
C5 C6 1.379(9) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C8 C9 1.373(9) . ?
C9 H9 0.9300 . ?
C9 C10 1.374(9) . ?
C10 H10 0.9300 . ?
C10 C11 1.382(9) . ?
C11 H11 0.9300 . ?
C11 C12 1.375(9) . ?
C12 H12 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
I3 I2 I1 177.209(19) . . ?
C8 N1 N2 123.5(5) . . ?
C12 N1 N2 114.4(5) . . ?
C12 N1 C8 121.9(5) . . ?
C7 N2 N1 115.0(5) . . ?
C2 C1 C6 119.7(6) . . ?
C2 C1 C7 122.1(6) . . ?
C6 C1 C7 118.1(6) . . ?
C1 C2 H2 120.7 . . ?
C3 C2 C1 118.6(6) . . ?
C3 C2 H2 120.7 . . ?
F1 C3 C2 119.6(6) . . ?
F1 C3 C4 117.2(6) . . ?
C2 C3 C4 123.2(6) . . ?
C3 C4 H4 121.2 . . ?
C5 C4 C3 117.6(7) . . ?
C5 C4 H4 121.2 . . ?
C4 C5 H5 119.6 . . ?
C6 C5 C4 120.7(7) . . ?
C6 C5 H5 119.6 . . ?
C1 C6 H6 119.9 . . ?
C5 C6 C1 120.2(6) . . ?
C5 C6 H6 119.9 . . ?
N2 C7 C1 119.8(6) . . ?
N2 C7 H7 120.1 . . ?
C1 C7 H7 120.1 . . ?
N1 C8 H8 120.2 . . ?
N1 C8 C9 119.6(6) . . ?
C9 C8 H8 120.2 . . ?
C8 C9 H9 120.1 . . ?
C8 C9 C10 119.7(6) . . ?
C10 C9 H9 120.1 . . ?
C9 C10 H10 120.2 . . ?
C9 C10 C11 119.6(6) . . ?
C11 C10 H10 120.2 . . ?
C10 C11 H11 120.1 . . ?
C12 C11 C10 119.8(6) . . ?
C12 C11 H11 120.1 . . ?
N1 C12 C11 119.3(6) . . ?
N1 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?

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
F1 C3 C4 C5 -179.1(5) . . . . ?
N1 N2 C7 C1 177.9(5) . . . . ?
N1 C8 C9 C10 1.0(10) . . . . ?
N2 N1 C8 C9 -176.9(5) . . . . ?
N2 N1 C12 C11 177.2(5) . . . . ?
C1 C2 C3 F1 179.0(5) . . . . ?
C1 C2 C3 C4 0.0(9) . . . . ?
C2 C1 C6 C5 0.6(9) . . . . ?
C2 C1 C7 N2 -4.6(9) . . . . ?
C2 C3 C4 C5 -0.1(9) . . . . ?
C3 C4 C5 C6 0.4(9) . . . . ?
C4 C5 C6 C1 -0.6(9) . . . . ?
C6 C1 C2 C3 -0.3(9) . . . . ?
C6 C1 C7 N2 175.8(6) . . . . ?
C7 C1 C2 C3 -179.9(6) . . . . ?
C7 C1 C6 C5 -179.8(6) . . . . ?
C8 N1 N2 C7 -38.4(8) . . . . ?
C8 N1 C12 C11 2.1(9) . . . . ?
C8 C9 C10 C11 0.4(10) . . . . ?
C9 C10 C11 C12 -0.6(10) . . . . ?
C10 C11 C12 N1 -0.6(10) . . . . ?
C12 N1 N2 C7 146.6(6) . . . . ?
C12 N1 C8 C9 -2.3(10) . . . . ?

_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 1.321
_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_01
_database_code_depnum_ccdc_archive 'CCDC 2041338'
loop_
_audit_author_name
_audit_author_address
Duan
;Nanjingxiaozhuang university
China
;
_audit_update_record             
;
2020-10-29 deposited with the CCDC.	2021-09-01 downloaded from the CCDC.
;
_audit_creation_date             2019-03-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(I1.5), C12 H10 F N2'
_chemical_formula_sum            'C12 H10 F I3 N2'
_chemical_formula_weight         581.92
_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'
F F 0.0171 0.0103 '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'

_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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   16.7765(14)
_cell_length_b                   12.5959(7)
_cell_length_c                   17.5833(16)
_cell_angle_alpha                90
_cell_angle_beta                 121.008(12)
_cell_angle_gamma                90
_cell_volume                     3184.6(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    5127
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      28.1170
_cell_measurement_theta_min      2.7150
_shelx_estimated_absorpt_T_max   0.650
_shelx_estimated_absorpt_T_min   0.539
_exptl_absorpt_coefficient_mu    5.884
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57029
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    2.427
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2112
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0642
_diffrn_reflns_av_unetI/netI     0.0551
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10189
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.115
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -59.00  38.00   1.00    1.00    --   11.74 -57.00 -30.00   97
  2  ω    -20.00  77.00   1.00    1.00    --   11.74  77.00-120.00   97
  3  ω    -14.00  82.00   1.00    1.00    --   11.74  57.00 120.00   96
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0087030000
_diffrn_orient_matrix_UB_12      -0.0066741000
_diffrn_orient_matrix_UB_13      -0.0437094000
_diffrn_orient_matrix_UB_21      0.0123638500
_diffrn_orient_matrix_UB_22      -0.0543603500
_diffrn_orient_matrix_UB_23      0.0090056000
_diffrn_orient_matrix_UB_31      -0.0469293000
_diffrn_orient_matrix_UB_32      -0.0130401000
_diffrn_orient_matrix_UB_33      -0.0149688000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2527
_reflns_number_total             2815
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         2.313
_refine_diff_density_min         -2.302
_refine_diff_density_rms         0.426
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.200
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2815
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0930
_refine_ls_R_factor_gt           0.0870
_refine_ls_restrained_S_all      1.198
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0430P)²+830.9156P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2341
_refine_ls_wR_factor_ref         0.2368
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Rigid bond restraints
 C6, C7
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
C6 \\sim C7: within 2A with sigma of 0.002 and sigma for terminal atoms of 0.004
4.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C1(H1), C9(H9), C8(H8), C4(H4), C5(H5), C11(H11), C2(H2),
 C10(H10)
;
_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
I3 I 0.000000 0.500000 0.000000 0.0148(2) Uani 1 2 d S T P . .
I1 I 0.500000 0.53007(9) 0.750000 0.0209(3) Uani 1 2 d S T P . .
I4 I 0.05424(5) 0.59769(7) 0.16937(5) 0.0260(2) Uani 1 1 d . . . . .
I2 I 0.62162(6) 0.52574(8) 0.67667(6) 0.0312(2) Uani 1 1 d . . . . .
F1 F 0.4469(5) 0.2709(7) 0.5668(5) 0.040(2) Uani 1 1 d . . . . .
N2 N 0.2735(6) 0.5170(8) 0.5141(7) 0.021(3) Uani 1 1 d . . . . .
N1 N 0.2881(6) 0.6063(8) 0.4704(6) 0.018(2) Uani 1 1 d . . . . .
C3 C 0.3019(8) 0.7845(10) 0.3936(8) 0.026(3) Uani 1 1 d . . . . .
H3 H 0.307196 0.845799 0.367059 0.031 Uiso 1 1 calc R . . . .
C6 C 0.3298(8) 0.4455(11) 0.5301(7) 0.0228(10) Uani 1 1 d . U . . .
H6 H 0.374477 0.450917 0.513913 0.027 Uiso 1 1 calc R . . . .
C1 C 0.3741(7) 0.6459(10) 0.4967(7) 0.022(3) Uani 1 1 d . . . . .
H1 H 0.427580 0.612668 0.540879 0.027 Uiso 1 1 calc R . . . .
C7 C 0.3235(7) 0.3503(11) 0.5763(7) 0.0220(10) Uani 1 1 d . U . . .
C9 C 0.2644(9) 0.2497(11) 0.6555(7) 0.027(3) Uani 1 1 d . . . . .
H9 H 0.221999 0.243249 0.674278 0.032 Uiso 1 1 calc R . . . .
C8 C 0.2629(8) 0.3409(11) 0.6089(8) 0.026(3) Uani 1 1 d . . . . .
H8 H 0.221517 0.395588 0.599596 0.031 Uiso 1 1 calc R . . . .
C12 C 0.3861(8) 0.2630(11) 0.5951(9) 0.028(3) Uani 1 1 d . . . . .
C4 C 0.2160(10) 0.7449(11) 0.3687(9) 0.032(4) Uani 1 1 d . . . . .
H4 H 0.162946 0.779189 0.324847 0.038 Uiso 1 1 calc R . . . .
C5 C 0.2073(7) 0.6544(11) 0.4081(7) 0.022(3) Uani 1 1 d . . . . .
H5 H 0.149419 0.627411 0.393061 0.027 Uiso 1 1 calc R . . . .
C11 C 0.3887(9) 0.1745(11) 0.6442(9) 0.033(4) Uani 1 1 d . . . . .
H11 H 0.430987 0.119971 0.656491 0.039 Uiso 1 1 calc R . . . .
C2 C 0.3793(8) 0.7344(11) 0.4569(8) 0.029(4) Uani 1 1 d . . . . .
H2 H 0.437431 0.761901 0.473083 0.035 Uiso 1 1 calc R . . . .
C10 C 0.3275(9) 0.1699(10) 0.6738(8) 0.029(4) Uani 1 1 d . . . . .
H10 H 0.328704 0.111595 0.706855 0.035 Uiso 1 1 calc R . . . .


_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
I3 I4 2.9016(9) . ?
I3 I4 2.9016(9) 5_565 ?
I1 I2 2.9222(11) 2_656 ?
I1 I2 2.9222(11) . ?
F1 C12 1.350(18) . ?
N2 N1 1.451(15) . ?
N2 C6 1.229(17) . ?
N1 C1 1.364(15) . ?
N1 C5 1.369(13) . ?
C3 H3 0.9300 . ?
C3 C4 1.37(2) . ?
C3 C2 1.354(16) . ?
C6 H6 0.9300 . ?
C6 C7 1.484(19) . ?
C1 H1 0.9300 . ?
C1 C2 1.34(2) . ?
C7 C8 1.41(2) . ?
C7 C12 1.436(18) . ?
C9 H9 0.9300 . ?
C9 C8 1.403(19) . ?
C9 C10 1.372(19) . ?
C8 H8 0.9300 . ?
C12 C11 1.40(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.38(2) . ?
C5 H5 0.9300 . ?
C11 H11 0.9300 . ?
C11 C10 1.37(2) . ?
C2 H2 0.9300 . ?
C10 H10 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
I4 I3 I4 180.0 . 5_565 ?
I2 I1 I2 177.86(6) . 2_656 ?
C6 N2 N1 111.7(12) . . ?
C1 N1 N2 122.8(8) . . ?
C1 N1 C5 123.2(11) . . ?
C5 N1 N2 113.6(10) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C2 C3 C4 120.0(13) . . ?
N2 C6 H6 121.5 . . ?
N2 C6 C7 117.0(13) . . ?
C7 C6 H6 121.5 . . ?
N1 C1 H1 121.0 . . ?
C2 C1 N1 118.0(10) . . ?
C2 C1 H1 121.0 . . ?
C8 C7 C6 124.2(12) . . ?
C8 C7 C12 116.0(12) . . ?
C12 C7 C6 119.7(12) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 H9 119.4 . . ?
C10 C9 C8 121.2(14) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 C7 120.4(12) . . ?
C9 C8 H8 119.8 . . ?
F1 C12 C7 117.4(12) . . ?
F1 C12 C11 119.8(12) . . ?
C11 C12 C7 122.7(14) . . ?
C3 C4 H4 119.8 . . ?
C3 C4 C5 120.4(11) . . ?
C5 C4 H4 119.8 . . ?
N1 C5 C4 116.8(11) . . ?
N1 C5 H5 121.6 . . ?
C4 C5 H5 121.6 . . ?
C12 C11 H11 120.7 . . ?
C10 C11 C12 118.5(13) . . ?
C10 C11 H11 120.7 . . ?
C3 C2 H2 119.3 . . ?
C1 C2 C3 121.5(12) . . ?
C1 C2 H2 119.3 . . ?
C9 C10 H10 119.4 . . ?
C11 C10 C9 121.1(13) . . ?
C11 C10 H10 119.4 . . ?

_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 1.583
_oxdiff_exptl_absorpt_empirical_full_min 0.669
