# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_preex1
_database_code_depnum_ccdc_archive 'CCDC 2086279'
loop_
_audit_author_name
_audit_author_address
'Emanuele Priola'
;University of Turin
Italy
;
_audit_update_record             
;
2021-05-27 deposited with the CCDC.	2022-03-07 downloaded from the CCDC.
;
_audit_creation_date             2020-06-15
_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         'C15 H11 Br2 Hg N3'
_chemical_formula_sum            'C15 H11 Br2 Hg N3'
_chemical_formula_weight         593.68
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
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'
Hg Hg -2.3894 9.2266 '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        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   11.7090(6)
_cell_length_b                   9.5059(5)
_cell_length_c                   13.9720(10)
_cell_angle_alpha                90
_cell_angle_beta                 95.422(6)
_cell_angle_gamma                90
_cell_volume                     1548.19(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3571
_cell_measurement_temperature    293
_cell_measurement_theta_max      29.1400
_cell_measurement_theta_min      3.9150
_shelx_estimated_absorpt_T_max   0.265
_shelx_estimated_absorpt_T_min   0.089
_exptl_absorpt_coefficient_mu    15.098
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.27116
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.547
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1088
_exptl_crystal_preparation       'slow evaporation of DMF'
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0410
_diffrn_reflns_av_unetI/netI     0.0271
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8803
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.367
_diffrn_reflns_theta_min         3.496
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1990
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -54.00  32.00   1.00   30.00    --  -29.89  37.00 -60.00   86
  2  ω    -53.00  45.00   1.00   30.00    --  -29.89  37.00  30.00   98
  3  ω     78.00 104.00   1.00   30.00    --   31.14  68.00  32.78   26
  4  ω      6.00  54.00   1.00   30.00    --   31.14 -37.00  30.00   48
  5  ω     15.00  50.00   1.00   30.00    --   31.14  70.00  77.71   35
  6  ω     10.00 101.00   1.00   30.00    --   31.14  70.00 -57.47   91
  7  ω    -21.00   4.00   1.00   30.00    --   31.14 -37.00  30.00   25
  8  ω      1.00  27.00   1.00   30.00    --   31.14  70.00-128.69   26
  9  ω      1.00  30.00   1.00   30.00    --   31.14  68.00 -89.91   29
 10  ω      0.00 102.00   1.00   30.00    --   31.14  70.00 151.79  102
 11  ω      7.00  44.00   1.00   30.00    --   31.14  68.00  32.78   37
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, AtlasS2, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0307038000
_diffrn_orient_matrix_UB_12      0.0384409000
_diffrn_orient_matrix_UB_13      -0.0376452000
_diffrn_orient_matrix_UB_21      0.0261843000
_diffrn_orient_matrix_UB_22      -0.0406888000
_diffrn_orient_matrix_UB_23      -0.0344456000
_diffrn_orient_matrix_UB_31      -0.0455407000
_diffrn_orient_matrix_UB_32      -0.0492642000
_diffrn_orient_matrix_UB_33      -0.0009189000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1483
_reflns_number_total             1587
_reflns_odcompleteness_completeness 99.70
_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 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.578
_refine_diff_density_min         -0.840
_refine_diff_density_rms         0.108
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     97
_refine_ls_number_reflns         1587
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0235
_refine_ls_R_factor_gt           0.0203
_refine_ls_restrained_S_all      1.072
_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)+(0.0220P)²+0.0194P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0459
_refine_ls_wR_factor_ref         0.0473
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C4(H4), C2(H2), C7(H7), C8(H8), C3(H3)
;
_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
Hg1 Hg 0.750000 0.23293(2) 0.500000 0.03417(8) Uani 1 2 d S T P . .
Br1 Br 0.85194(4) 0.10275(5) 0.37249(4) 0.04883(13) Uani 1 1 d . . . . .
C5 C 0.5724(3) 0.4694(4) 0.4003(3) 0.0317(8) Uani 1 1 d . . . . .
N1 N 0.5857(2) 0.3290(3) 0.4061(2) 0.0335(7) Uani 1 1 d . . . . .
C6 C 0.6637(3) 0.5567(4) 0.4524(3) 0.0316(8) Uani 1 1 d . . . . .
C1 C 0.5065(4) 0.2450(4) 0.3612(3) 0.0426(10) Uani 1 1 d . . . . .
H1 H 0.516286 0.148160 0.366769 0.051 Uiso 1 1 calc R . . . .
C4 C 0.4770(3) 0.5270(5) 0.3469(3) 0.0434(10) Uani 1 1 d . . . . .
H4 H 0.467598 0.624050 0.342619 0.052 Uiso 1 1 calc R . . . .
C2 C 0.4115(4) 0.2955(5) 0.3073(3) 0.0496(11) Uani 1 1 d . . . . .
H2 H 0.358391 0.234044 0.276223 0.059 Uiso 1 1 calc R . . . .
C7 C 0.6609(4) 0.7016(4) 0.4521(3) 0.0416(10) Uani 1 1 d . . . . .
H7 H 0.599492 0.749333 0.419834 0.050 Uiso 1 1 calc R . . . .
C8 C 0.750000 0.7747(6) 0.500000 0.0476(16) Uani 1 2 d S T P . .
H8 H 0.749999 0.872506 0.500001 0.057 Uiso 1 2 calc RS T P . .
C3 C 0.3961(3) 0.4372(5) 0.3000(3) 0.0507(12) Uani 1 1 d . . . . .
H3 H 0.332023 0.473723 0.264039 0.061 Uiso 1 1 calc R . . . .
N2 N 0.750000 0.4870(4) 0.500000 0.0280(9) Uani 1 2 d S T P . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Hg1 Br1 2.5557(5) . ?
Hg1 Br1 2.5558(5) 2_656 ?
Hg1 N1 2.404(3) . ?
Hg1 N1 2.404(3) 2_656 ?
Hg1 N2 2.415(4) . ?
C5 N1 1.345(5) . ?
C5 C6 1.487(5) . ?
C5 C4 1.396(5) . ?
N1 C1 1.334(5) . ?
C6 C7 1.378(5) . ?
C6 N2 1.332(4) . ?
C1 C2 1.371(6) . ?
C4 C3 1.392(6) . ?
C2 C3 1.362(7) . ?
C7 C8 1.374(5) . ?

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
Br1 Hg1 Br1 122.08(2) . 2_656 ?
N1 Hg1 Br1 101.89(8) . . ?
N1 Hg1 Br1 101.89(8) 2_656 2_656 ?
N1 Hg1 Br1 99.31(7) . 2_656 ?
N1 Hg1 Br1 99.31(7) 2_656 . ?
N1 Hg1 N1 135.35(15) . 2_656 ?
N1 Hg1 N2 67.67(8) . . ?
N1 Hg1 N2 67.67(7) 2_656 . ?
N2 Hg1 Br1 118.958(11) . 2_656 ?
N2 Hg1 Br1 118.959(12) . . ?
N1 C5 C6 116.8(3) . . ?
N1 C5 C4 120.2(4) . . ?
C4 C5 C6 123.0(4) . . ?
C5 N1 Hg1 119.5(2) . . ?
C1 N1 Hg1 120.9(3) . . ?
C1 N1 C5 119.6(3) . . ?
C7 C6 C5 122.7(3) . . ?
N2 C6 C5 116.3(3) . . ?
N2 C6 C7 121.0(4) . . ?
N1 C1 C2 122.7(4) . . ?
C3 C4 C5 119.1(4) . . ?
C3 C2 C1 118.8(4) . . ?
C8 C7 C6 119.2(4) . . ?
C7 C8 C7 119.2(6) 2_656 . ?
C2 C3 C4 119.5(4) . . ?
C6 N2 Hg1 119.8(2) 2_656 . ?
C6 N2 Hg1 119.8(2) . . ?
C6 N2 C6 120.4(5) . 2_656 ?

_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 2.837
_oxdiff_exptl_absorpt_empirical_full_min 0.685
####################################################################### 
# 
# 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_conass
_database_code_depnum_ccdc_archive 'CCDC 2086285'
loop_
_audit_author_name
_audit_author_address
'Emanuele Priola'
;University of Turin
Italy
;
_audit_update_record             
;
2021-05-27 deposited with the CCDC.	2022-03-07 downloaded from the CCDC.
;
_audit_creation_date             2020-03-18
_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         'Br Hg I'
_chemical_formula_sum            'Br Hg I'
_chemical_formula_weight         407.40
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Hg Hg -2.3894 9.2266 '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'

_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           36
_space_group_name_H-M_alt        'C m c 21'
_space_group_name_Hall           'C 2c -2'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, 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'
'-x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   4.6816(11)
_cell_length_b                   7.1488(15)
_cell_length_c                   13.371(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     447.48(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    307
_cell_measurement_temperature    295
_cell_measurement_theta_max      26.0230
_cell_measurement_theta_min      5.1880
_shelx_estimated_absorpt_T_max   0.032
_shelx_estimated_absorpt_T_min   0.020
_exptl_absorpt_coefficient_mu    49.995
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.13272
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    6.047
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             672
_exptl_crystal_recrystallization_method 'recrystallization from acetone'
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.22
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_av_unetI/netI     0.0434
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.895
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            876
_diffrn_reflns_point_group_measured_fraction_full 0.821
_diffrn_reflns_point_group_measured_fraction_max 0.690
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.227
_diffrn_reflns_theta_min         4.573
_diffrn_ambient_temperature      295.0
_diffrn_detector_area_resol_mean 10.2890
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.895
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     33.00  85.00   1.00    7.50    --   10.45   0.00   0.00   52
  2  ω    -54.00  31.00   1.00    7.50    --   10.45   0.00   0.00   85
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.483
_reflns_Friedel_fraction_full    0.633
_reflns_Friedel_fraction_max     0.468
_reflns_number_gt                399
_reflns_number_total             467
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         1.281
_refine_diff_density_min         -1.962
_refine_diff_density_rms         0.346
_refine_ls_abs_structure_details 
;
 Flack x determined using 120 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    undef
_refine_ls_matrix_type           full
_refine_ls_number_parameters     20
_refine_ls_number_reflns         467
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0523
_refine_ls_R_factor_gt           0.0432
_refine_ls_restrained_S_all      1.095
_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)+(0.0501P)²+6.7671P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1003
_refine_ls_wR_factor_ref         0.1116
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.45(5)
 0.55(5)
2. Shared sites
{Br1, I2}
{I1, Br2}
3. Uiso/Uaniso restraints and constraints
Uanis(Br2) = Uanis(I1)
Uanis(Br1) = Uanis(I2)
Uanis(I1) = Uanis(Br2)
4. Others
 Fixed Sof: Br2(0.25) I2(0.25) Br1(0.25) I1(0.25)
;
_atom_sites_solution_hydrogens   .
_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
Hg1 Hg -0.500000 -0.1625(3) 0.0543(2) 0.0594(6) Uani 1 2 d S T P . .
Br2 Br -0.500000 0.0962(5) 0.18763(19) 0.0455(9) Uani 0.5 2 d S T P A 2
I2 I -0.500000 -0.4217(5) -0.0759(2) 0.0457(9) Uani 0.5 2 d S T P A 2
Br1 Br -0.500000 -0.4217(5) -0.0759(2) 0.0457(9) Uani 0.5 2 d S T P A 1
I1 I -0.500000 0.0962(5) 0.18763(19) 0.0455(9) Uani 0.5 2 d S T P A 1


_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
Hg1 Br2 2.569(3) . ?
Hg1 I2 2.542(4) . ?
Hg1 Br1 2.542(4) . ?
Hg1 I1 2.569(3) . ?

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 Hg1 Br2 179.27(17) . . ?
Br1 Hg1 I1 179.27(17) . . ?

_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
;
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.45(5)
2 0.55(5)

####################################################################### 
# 
# 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_preex1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2086288'
loop_
_audit_author_name
_audit_author_address
'Emanuele Priola'
;University of Turin
Italy
;
_audit_update_record             
;
2021-05-27 deposited with the CCDC.	2022-03-07 downloaded from the CCDC.
;
_audit_creation_date             2020-07-03
_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         '0.5(C20 H16 Br2 Hg2 I2 N4)'
_chemical_formula_sum            'C10 H8 Br Hg I N2'
_chemical_formula_weight         563.58
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
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'
Hg Hg -2.3894 9.2266 '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           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'

_cell_length_a                   8.6933(5)
_cell_length_b                   9.1875(7)
_cell_length_c                   9.4039(8)
_cell_angle_alpha                118.877(8)
_cell_angle_beta                 102.032(6)
_cell_angle_gamma                96.897(5)
_cell_volume                     621.51(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2967
_cell_measurement_temperature    299
_cell_measurement_theta_max      24.4420
_cell_measurement_theta_min      3.4820
_shelx_estimated_absorpt_T_max   0.293
_shelx_estimated_absorpt_T_min   0.173
_exptl_absorpt_coefficient_mu    18.049
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51775
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    3.012
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             500
_exptl_crystal_size_max          0.15
_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  0.0665
_diffrn_reflns_av_unetI/netI     0.0990
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            17090
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.507
_diffrn_reflns_theta_min         3.471
_diffrn_ambient_temperature      299
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1990
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     20.00  46.00   1.00   25.00    --  -29.89  17.00-141.00   26
  2  ω    -27.00  -1.00   1.00   25.00    --  -29.89  17.00-141.00   26
  3  ω     64.00 112.00   1.00   25.00    --   31.14  17.00-141.00   48
  4  ω     32.00  61.00   1.00   25.00    --   31.14  17.00-141.00   29
  5  ω    -67.00 -19.00   1.00   25.00    --  -29.89 -17.00  49.00   48
  6  ω   -109.00 -79.00   1.00   25.00    --  -29.89 -17.00  49.00   30
  7  ω    -50.00 -10.00   1.00   25.00    --   31.14 -17.00  49.00   40
  8  ω    -43.00  62.00   1.00   25.00    --   31.14 -70.00-103.46  105
  9  ω      2.00 103.00   1.00   25.00    --   31.14  67.00  11.98  101
 10  ω    -43.00  62.00   1.00   25.00    --   31.14 -70.00  -1.75  105
 11  ω    -33.00  62.00   1.00   25.00    --   31.14 -70.00 167.23   95
 12  ω    -38.00  61.00   1.00   25.00    --   31.14 -70.00  94.35   99
 13  ω      0.00  49.00   1.00   25.00    --   31.14  70.00-136.82   49
 14  ω     65.00  98.00   1.00   25.00    --   31.14  70.00-136.82   33
 15  ω      6.00 105.00   1.00   25.00    --   31.14  70.00 101.31   99
 16  ω      1.00 105.00   1.00   25.00    --   31.14  69.00 -68.85  104
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, AtlasS2, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0143977000
_diffrn_orient_matrix_UB_12      0.0091451000
_diffrn_orient_matrix_UB_13      0.0813254000
_diffrn_orient_matrix_UB_21      -0.0147388000
_diffrn_orient_matrix_UB_22      -0.0905390000
_diffrn_orient_matrix_UB_23      -0.0389207000
_diffrn_orient_matrix_UB_31      0.0838476000
_diffrn_orient_matrix_UB_32      0.0067352000
_diffrn_orient_matrix_UB_33      0.0077551000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.997
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                4065
_reflns_number_total             7555
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.44
_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 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         1.039
_refine_diff_density_min         -1.153
_refine_diff_density_rms         0.175
_refine_ls_abs_structure_details 
;
 Flack x determined using 1353 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.48(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.987
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         7555
_refine_ls_number_restraints     195
_refine_ls_R_factor_all          0.1215
_refine_ls_R_factor_gt           0.0521
_refine_ls_restrained_S_all      0.980
_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)+(0.0179P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0748
_refine_ls_wR_factor_ref         0.0978
_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(Hg1) \\sim Ueq, Uanis(I1) \\sim Ueq, Uanis(Br1)
\\sim Ueq, Uanis(N1) \\sim Ueq, Uanis(N2) \\sim Ueq, Uanis(C5) \\sim Ueq,
Uanis(C6) \\sim Ueq, Uanis(C10) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(C4) \\sim
Ueq, Uanis(C7) \\sim Ueq, Uanis(C9) \\sim Ueq, Uanis(C3) \\sim Ueq, Uanis(C8)
\\sim Ueq, : with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(N3) \\sim Ueq, Uanis(Hg2) \\sim Ueq, Uanis(Br1A) \\sim Ueq, Uanis(I1A)
\\sim Ueq, Uanis(N4) \\sim Ueq, Uanis(I1B) \\sim Ueq, Uanis(Br1B) \\sim Ueq,
Uanis(C16) \\sim Ueq, Uanis(C20) \\sim Ueq, Uanis(C15) \\sim Ueq, Uanis(C11)
\\sim Ueq, Uanis(C17) \\sim Ueq, Uanis(C19) \\sim Ueq, Uanis(C14) \\sim Ueq,
Uanis(C12) \\sim Ueq, Uanis(C18) \\sim Ueq, Uanis(C13) \\sim Ueq, : with sigma
of 0.01 and sigma for terminal atoms of 0.02
3. Others
 Sof(I1B)=Sof(Br1B)=1-FVAR(1)
 Sof(Br1A)=Sof(I1A)=FVAR(1)
4.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C4(H4), C7(H7), C10(H10), C9(H9), C8(H8), C2(H2), C3(H3), C12(H12),
 C14(H14), C18(H18), C19(H19), C13(H13), C17(H17), C20(H20), C11(H11)
;
_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
Hg1 Hg 0.22916(10) 0.16206(11) 0.28532(12) 0.0570(6) Uani 1 1 d . U . . .
Hg2 Hg -0.19216(10) 0.67938(11) 0.97916(12) 0.0572(6) Uani 1 1 d . U . . .
I1 I 0.5004(4) 0.1197(5) 0.4268(5) 0.0716(12) Uani 1 1 d . U . . .
Br1A Br 0.077(2) 0.751(3) 0.923(3) 0.073(5) Uani 0.650(10) 1 d . U P A 1
I1A I -0.4628(14) 0.7175(16) 0.8300(13) 0.0499(19) Uani 0.650(10) 1 d . U P A 1
Br1 Br -0.0455(6) 0.0811(7) 0.3294(8) 0.0466(12) Uani 1 1 d . U . . .
C1 C 0.333(5) 0.116(5) -0.056(5) 0.057(11) Uani 1 1 d . U . . .
H1 H 0.327283 0.005892 -0.074532 0.069 Uiso 1 1 calc R U . . .
N1 N 0.286(4) 0.223(4) 0.078(4) 0.041(7) Uani 1 1 d . U . . .
C6 C 0.224(4) 0.496(4) 0.251(5) 0.033(7) Uani 1 1 d . U . . .
N2 N 0.203(4) 0.447(4) 0.355(4) 0.040(7) Uani 1 1 d . U . . .
C4 C 0.329(4) 0.419(4) -0.010(5) 0.037(7) Uani 1 1 d . U . . .
H4 H 0.328439 0.527376 0.006001 0.045 Uiso 1 1 calc R U . . .
C7 C 0.208(4) 0.649(5) 0.270(5) 0.044(9) Uani 1 1 d . U . . .
H7 H 0.226790 0.682050 0.194877 0.053 Uiso 1 1 calc R U . . .
C5 C 0.282(4) 0.376(5) 0.092(5) 0.048(9) Uani 1 1 d . U . . .
C10 C 0.149(5) 0.540(6) 0.481(6) 0.056(11) Uani 1 1 d . U . . .
H10 H 0.126904 0.497331 0.548767 0.067 Uiso 1 1 calc R U . . .
C9 C 0.122(5) 0.701(5) 0.519(6) 0.053(10) Uani 1 1 d . U . . .
H9 H 0.083101 0.766567 0.608410 0.064 Uiso 1 1 calc R U . . .
C8 C 0.160(5) 0.755(5) 0.413(6) 0.049(10) Uani 1 1 d . U . . .
H8 H 0.152523 0.864494 0.436197 0.059 Uiso 1 1 calc R U . . .
C2 C 0.384(5) 0.143(6) -0.160(7) 0.061(11) Uani 1 1 d . U . . .
H2 H 0.422863 0.064807 -0.243011 0.074 Uiso 1 1 calc R U . . .
C3 C 0.376(5) 0.307(6) -0.137(6) 0.057(11) Uani 1 1 d . U . . .
H3 H 0.403917 0.335822 -0.212300 0.068 Uiso 1 1 calc R U . . .
N4 N -0.247(4) 0.619(4) 1.178(5) 0.047(8) Uani 1 1 d . U . . .
N3 N -0.159(4) 0.403(5) 0.915(5) 0.049(8) Uani 1 1 d . U . . .
C12 C -0.100(5) 0.136(6) 0.742(7) 0.066(12) Uani 1 1 d . U . . .
H12 H -0.070403 0.065292 0.646439 0.079 Uiso 1 1 calc R U . . .
C14 C -0.180(5) 0.185(5) 0.979(6) 0.052(11) Uani 1 1 d . U . . .
H14 H -0.205067 0.143001 1.046236 0.063 Uiso 1 1 calc R U . . .
C18 C -0.326(5) 0.530(6) 1.406(7) 0.067(12) Uani 1 1 d . U . . .
H18 H -0.348030 0.502732 1.484727 0.080 Uiso 1 1 calc R U . . .
C19 C -0.341(5) 0.681(6) 1.421(6) 0.056(10) Uani 1 1 d . U . . .
H19 H -0.375791 0.758671 1.508523 0.067 Uiso 1 1 calc R U . . .
C16 C -0.241(3) 0.464(4) 1.156(4) 0.031(7) Uani 1 1 d . U . . .
C15 C -0.198(4) 0.343(5) 1.017(5) 0.041(8) Uani 1 1 d . U . . .
C13 C -0.125(6) 0.085(6) 0.847(7) 0.067(13) Uani 1 1 d . U . . .
H13 H -0.106141 -0.018736 0.831087 0.080 Uiso 1 1 calc R U . . .
C17 C -0.278(5) 0.414(5) 1.268(5) 0.057(10) Uani 1 1 d . U . . .
H17 H -0.269882 0.306825 1.251425 0.069 Uiso 1 1 calc R U . . .
C20 C -0.301(4) 0.724(5) 1.297(5) 0.044(8) Uani 1 1 d . U . . .
H20 H -0.314851 0.826356 1.305212 0.053 Uiso 1 1 calc R U . . .
C11 C -0.118(5) 0.293(6) 0.778(6) 0.053(11) Uani 1 1 d . U . . .
H11 H -0.100604 0.327369 0.702945 0.063 Uiso 1 1 calc R U . . .
I1B I 0.087(2) 0.769(3) 0.944(3) 0.058(4) Uani 0.350(10) 1 d . U P A 2
Br1B Br -0.467(4) 0.740(5) 0.873(4) 0.050(5) Uani 0.350(10) 1 d . U P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Hg1 I1 2.626(4) . ?
Hg1 Br1 2.591(5) . ?
Hg1 N1 2.40(3) . ?
Hg1 N2 2.43(3) . ?
Hg1 I1B 3.31(3) 1_544 ?
Hg2 Br1A 2.584(15) . ?
Hg2 I1A 2.631(13) . ?
Hg2 N4 2.30(3) . ?
Hg2 N3 2.38(3) . ?
Hg2 I1B 2.605(19) . ?
Hg2 Br1B 2.62(3) . ?
C1 N1 1.35(5) . ?
C1 C2 1.27(6) . ?
N1 C5 1.36(5) . ?
C6 N2 1.29(4) . ?
C6 C7 1.36(5) . ?
C6 C5 1.60(5) . ?
N2 C10 1.30(5) . ?
C4 C5 1.32(5) . ?
C4 C3 1.33(5) . ?
C7 C8 1.41(6) . ?
C10 C9 1.41(5) . ?
C9 C8 1.39(6) . ?
C2 C3 1.42(6) . ?
N4 C16 1.35(4) . ?
N4 C20 1.30(5) . ?
N3 C15 1.39(5) . ?
N3 C11 1.36(5) . ?
C12 C13 1.33(7) . ?
C12 C11 1.35(5) . ?
C14 C15 1.36(5) . ?
C14 C13 1.36(7) . ?
C18 C19 1.36(6) . ?
C18 C17 1.42(6) . ?
C19 C20 1.48(6) . ?
C16 C15 1.41(5) . ?
C16 C17 1.42(5) . ?

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 Hg1 I1B 97.8(3) . 1_544 ?
Br1 Hg1 I1 122.71(13) . . ?
Br1 Hg1 I1B 81.7(3) . 1_544 ?
N1 Hg1 I1 105.5(7) . . ?
N1 Hg1 Br1 130.5(7) . . ?
N1 Hg1 N2 69.3(11) . . ?
N1 Hg1 I1B 81.1(9) . 1_544 ?
N2 Hg1 I1 120.7(7) . . ?
N2 Hg1 Br1 93.1(7) . . ?
N2 Hg1 I1B 136.0(8) . 1_544 ?
Br1A Hg2 I1A 121.0(4) . . ?
N4 Hg2 Br1A 131.7(9) . . ?
N4 Hg2 I1A 106.7(8) . . ?
N4 Hg2 N3 69.0(12) . . ?
N4 Hg2 I1B 129.5(9) . . ?
N4 Hg2 Br1B 100.5(10) . . ?
N3 Hg2 Br1A 91.0(9) . . ?
N3 Hg2 I1A 121.6(9) . . ?
N3 Hg2 I1B 92.9(9) . . ?
N3 Hg2 Br1B 124.6(12) . . ?
I1B Hg2 Br1B 127.0(8) . . ?
C2 C1 N1 129(4) . . ?
C1 N1 Hg1 125(3) . . ?
C1 N1 C5 114(3) . . ?
C5 N1 Hg1 121(3) . . ?
N2 C6 C7 125(4) . . ?
N2 C6 C5 119(3) . . ?
C7 C6 C5 116(3) . . ?
C6 N2 Hg1 118(3) . . ?
C6 N2 C10 120(4) . . ?
C10 N2 Hg1 121(3) . . ?
C5 C4 C3 120(4) . . ?
C6 C7 C8 115(4) . . ?
N1 C5 C6 112(3) . . ?
C4 C5 N1 122(4) . . ?
C4 C5 C6 126(3) . . ?
N2 C10 C9 123(4) . . ?
C8 C9 C10 115(5) . . ?
C9 C8 C7 122(4) . . ?
C1 C2 C3 113(4) . . ?
C4 C3 C2 121(4) . . ?
C16 N4 Hg2 119(3) . . ?
C20 N4 Hg2 121(2) . . ?
C20 N4 C16 120(3) . . ?
C15 N3 Hg2 118(3) . . ?
C11 N3 Hg2 125(3) . . ?
C11 N3 C15 117(4) . . ?
C13 C12 C11 118(5) . . ?
C15 C14 C13 123(4) . . ?
C19 C18 C17 118(5) . . ?
C18 C19 C20 120(4) . . ?
N4 C16 C15 121(3) . . ?
N4 C16 C17 123(4) . . ?
C15 C16 C17 117(3) . . ?
N3 C15 C16 114(3) . . ?
C14 C15 N3 118(4) . . ?
C14 C15 C16 128(4) . . ?
C12 C13 C14 120(5) . . ?
C18 C17 C16 118(4) . . ?
N4 C20 C19 120(4) . . ?
C12 C11 N3 124(4) . . ?
Hg2 I1B Hg1 100.0(7) . 1_566 ?

_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 1.712
_oxdiff_exptl_absorpt_empirical_full_min 0.754
####################################################################### 
# 
# 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_expm
_database_code_depnum_ccdc_archive 'CCDC 2086281'
loop_
_audit_author_name
_audit_author_address
'Emanuele Priola'
;University of Turin
Italy
;
_audit_update_record             
;
2021-05-27 deposited with the CCDC.	2022-03-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C36 H30 Br2 Hg2 I2 P2'
_chemical_formula_sum            'C36 H30 Br2 Hg2 I2 P2'
_chemical_formula_weight         1339.32

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'
P P 0.1023 0.0942 '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'
Hg Hg -2.3894 9.2266 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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                   19.1080(13)
_cell_length_b                   11.0409(8)
_cell_length_c                   18.9354(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.485(7)
_cell_angle_gamma                90.00
_cell_volume                     3994.6(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3595
_cell_measurement_theta_min      3.5340
_cell_measurement_theta_max      22.8620

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.21
_exptl_crystal_density_diffrn    2.227
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2448.0
_exptl_absorpt_coefficient_mu    11.326
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.53177
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      293(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  'Xcalibur, Ruby, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.2890
_diffrn_standards_number         24445
_diffrn_reflns_number            20018
_diffrn_reflns_av_R_equivalents  0.0686
_diffrn_reflns_av_sigmaI/netI    0.0884
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.54
_diffrn_reflns_theta_max         25.03
_reflns_number_total             7045
_reflns_number_gt                4210
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXP-97 (Sheldrick, 1997)'
_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)+(0.0191P)²+0.0000P] 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         7045
_refine_ls_number_parameters     397
_refine_ls_number_restraints     414
_refine_ls_R_factor_all          0.1076
_refine_ls_R_factor_gt           0.0517
_refine_ls_wR_factor_ref         0.0980
_refine_ls_wR_factor_gt          0.0787
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      0.989
_refine_ls_shift/su_max          0.024
_refine_ls_shift/su_mean         0.003

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
Hg1 Hg 0.32401(2) 0.86132(4) 0.16466(3) 0.05865(15) Uani 1 1 d . . .
Hg2 Hg 0.18999(2) 0.91818(4) 0.31670(3) 0.06206(16) Uani 1 1 d . . .
I2 I 0.32314(5) 1.02034(9) 0.27998(6) 0.0703(3) Uani 0.50 1 d P . .
Br2A Br 0.32314(5) 1.02034(9) 0.27998(6) 0.0703(3) Uani 0.50 1 d P . .
I1 I 0.18899(5) 0.75877(8) 0.20283(6) 0.0719(3) Uani 0.50 1 d P . .
Br1A Br 0.18899(5) 0.75877(8) 0.20283(6) 0.0719(3) Uani 0.50 1 d P . .
Br2 Br 0.21075(5) 0.79232(9) 0.43381(5) 0.0703(3) Uani 0.50 1 d P . .
I2A I 0.21075(5) 0.79232(9) 0.43381(5) 0.0703(3) Uani 0.50 1 d P . .
Br1 Br 0.30235(5) 0.99391(9) 0.05337(5) 0.0734(3) Uani 0.50 1 d P . .
I1A I 0.30235(5) 0.99391(9) 0.05337(5) 0.0734(3) Uani 0.50 1 d P . .
P2 P 0.10637(13) 1.0849(2) 0.29599(17) 0.0512(8) Uani 1 1 d . . .
P1 P 0.40166(13) 0.6874(2) 0.18451(16) 0.0504(8) Uani 1 1 d . . .
C19 C 0.1461(5) 1.2285(10) 0.3141(7) 0.063(3) Uani 1 1 d U . .
C31 C 0.0722(5) 1.0897(9) 0.2068(6) 0.052(3) Uani 1 1 d U . .
C25 C 0.0314(5) 1.0709(10) 0.3537(6) 0.056(3) Uani 1 1 d U . .
C6 C 0.4995(5) 0.6619(10) 0.2937(7) 0.068(3) Uani 1 1 d U . .
H6 H 0.5332 0.6563 0.2588 0.082 Uiso 1 1 calc R . .
C1 C 0.4299(5) 0.6775(9) 0.2746(6) 0.056(3) Uani 1 1 d U . .
C13 C 0.4795(5) 0.6970(10) 0.1298(6) 0.054(3) Uani 1 1 d U . .
C14 C 0.5066(5) 0.5942(11) 0.0979(7) 0.072(3) Uani 1 1 d U . .
H14 H 0.4846 0.5198 0.1034 0.087 Uiso 1 1 calc R . .
C2 C 0.3809(6) 0.6890(11) 0.3283(6) 0.071(3) Uani 1 1 d U . .
H2 H 0.3341 0.7011 0.3167 0.085 Uiso 1 1 calc R . .
C7 C 0.3560(5) 0.5494(9) 0.1613(7) 0.059(3) Uani 1 1 d U . .
C32 C 0.1197(7) 1.0766(10) 0.1502(7) 0.076(3) Uani 1 1 d U . .
H32 H 0.1670 1.0641 0.1597 0.091 Uiso 1 1 calc R . .
C28 C -0.0824(6) 1.0410(14) 0.4389(8) 0.090(4) Uani 1 1 d U . .
H28 H -0.1212 1.0310 0.4676 0.108 Uiso 1 1 calc R . .
C15 C 0.5677(6) 0.6032(13) 0.0572(7) 0.087(4) Uani 1 1 d U . .
H15 H 0.5852 0.5365 0.0331 0.104 Uiso 1 1 calc R . .
C27 C -0.0577(6) 1.1568(13) 0.4264(7) 0.087(4) Uani 1 1 d U . .
H27 H -0.0789 1.2241 0.4466 0.104 Uiso 1 1 calc R . .
C26 C -0.0009(5) 1.1686(11) 0.3832(7) 0.074(3) Uani 1 1 d U . .
H26 H 0.0162 1.2457 0.3737 0.089 Uiso 1 1 calc R . .
C9 C 0.3199(7) 0.3355(11) 0.1833(9) 0.096(4) Uani 1 1 d U . .
H9 H 0.3204 0.2646 0.2098 0.115 Uiso 1 1 calc R . .
C10 C 0.2833(8) 0.3457(15) 0.1230(11) 0.114(5) Uani 1 1 d U . .
H10 H 0.2572 0.2784 0.1095 0.136 Uiso 1 1 calc R . .
C3 C 0.4010(7) 0.6826(13) 0.3978(7) 0.090(4) Uani 1 1 d U . .
H3 H 0.3675 0.6907 0.4328 0.108 Uiso 1 1 calc R . .
C17 C 0.5745(6) 0.8135(13) 0.0842(8) 0.088(4) Uani 1 1 d U . .
H17 H 0.5966 0.8878 0.0782 0.105 Uiso 1 1 calc R . .
C36 C 0.0028(6) 1.1095(10) 0.1916(7) 0.077(3) Uani 1 1 d U . .
H36 H -0.0291 1.1191 0.2280 0.092 Uiso 1 1 calc R . .
C24 C 0.1391(6) 1.3262(11) 0.2704(8) 0.086(4) Uani 1 1 d U . .
H24 H 0.1133 1.3208 0.2287 0.103 Uiso 1 1 calc R . .
C33 C 0.0968(9) 1.0820(12) 0.0824(8) 0.101(4) Uani 1 1 d U . .
H33 H 0.1280 1.0720 0.0455 0.122 Uiso 1 1 calc R . .
C16 C 0.6010(6) 0.7141(15) 0.0543(8) 0.092(4) Uani 1 1 d U . .
H16 H 0.6433 0.7198 0.0307 0.110 Uiso 1 1 calc R . .
C8 C 0.3594(7) 0.4446(12) 0.2047(9) 0.097(4) Uani 1 1 d U . .
H8 H 0.3862 0.4446 0.2460 0.117 Uiso 1 1 calc R . .
C5 C 0.5195(7) 0.6546(13) 0.3637(8) 0.095(4) Uani 1 1 d U . .
H5 H 0.5665 0.6433 0.3752 0.114 Uiso 1 1 calc R . .
C29 C -0.0522(7) 0.9425(13) 0.4108(8) 0.095(4) Uani 1 1 d U . .
H29 H -0.0698 0.8655 0.4194 0.114 Uiso 1 1 calc R . .
C34 C 0.0266(9) 1.1026(13) 0.0683(9) 0.107(5) Uani 1 1 d U . .
H34 H 0.0112 1.1078 0.0217 0.129 Uiso 1 1 calc R . .
C20 C 0.1833(7) 1.2418(14) 0.3778(9) 0.104(4) Uani 1 1 d U . .
H20 H 0.1873 1.1765 0.4085 0.125 Uiso 1 1 calc R . .
C23 C 0.1707(8) 1.4309(14) 0.2894(12) 0.130(5) Uani 1 1 d U . .
H23 H 0.1670 1.4963 0.2586 0.156 Uiso 1 1 calc R . .
C21 C 0.2137(9) 1.3506(17) 0.3950(12) 0.143(6) Uani 1 1 d U . .
H21 H 0.2387 1.3585 0.4371 0.172 Uiso 1 1 calc R . .
C22 C 0.2074(9) 1.4468(17) 0.3506(13) 0.140(7) Uani 1 1 d U . .
H22 H 0.2275 1.5212 0.3617 0.168 Uiso 1 1 calc R . .
C30 C 0.0054(6) 0.9585(12) 0.3691(8) 0.086(4) Uani 1 1 d U . .
H30 H 0.0275 0.8906 0.3507 0.103 Uiso 1 1 calc R . .
C12 C 0.3164(5) 0.5480(11) 0.1010(8) 0.075(3) Uani 1 1 d U . .
H12 H 0.3134 0.6179 0.0737 0.090 Uiso 1 1 calc R . .
C18 C 0.5142(6) 0.8061(11) 0.1242(7) 0.073(3) Uani 1 1 d U . .
H18 H 0.4973 0.8744 0.1472 0.088 Uiso 1 1 calc R . .
C4 C 0.4708(7) 0.6640(14) 0.4168(8) 0.100(4) Uani 1 1 d U . .
H4 H 0.4842 0.6581 0.4640 0.120 Uiso 1 1 calc R . .
C11 C 0.2800(6) 0.4436(12) 0.0789(8) 0.086(4) Uani 1 1 d U . .
H11 H 0.2550 0.4414 0.0366 0.103 Uiso 1 1 calc R . .
C35 C -0.0200(8) 1.1152(13) 0.1210(9) 0.101(4) Uani 1 1 d U . .
H35 H -0.0671 1.1276 0.1105 0.121 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
Hg1 P1 2.454(3) . ?
Hg1 Br1 2.5962(11) . ?
Hg1 I2 2.8021(11) . ?
Hg1 I1 2.9141(10) . ?
Hg2 P2 2.467(3) . ?
Hg2 Br2 2.6439(11) . ?
Hg2 I1 2.7832(11) . ?
Hg2 I2 2.8738(9) . ?
P2 C19 1.790(11) . ?
P2 C31 1.807(11) . ?
P2 C25 1.815(10) . ?
P1 C1 1.788(12) . ?
P1 C7 1.808(11) . ?
P1 C13 1.823(10) . ?
C19 C24 1.365(16) . ?
C19 C20 1.401(18) . ?
C31 C36 1.371(13) . ?
C31 C32 1.419(15) . ?
C25 C26 1.364(14) . ?
C25 C30 1.369(15) . ?
C6 C5 1.378(17) . ?
C6 C1 1.386(13) . ?
C1 C2 1.392(14) . ?
C13 C18 1.381(14) . ?
C13 C14 1.388(14) . ?
C14 C15 1.408(14) . ?
C2 C3 1.370(16) . ?
C7 C12 1.364(16) . ?
C7 C8 1.420(16) . ?
C32 C33 1.354(17) . ?
C28 C29 1.343(16) . ?
C28 C27 1.383(17) . ?
C15 C16 1.380(16) . ?
C27 C26 1.372(14) . ?
C9 C10 1.34(2) . ?
C9 C8 1.476(18) . ?
C10 C11 1.37(2) . ?
C3 C4 1.394(16) . ?
C17 C16 1.337(17) . ?
C17 C18 1.386(14) . ?
C36 C35 1.405(18) . ?
C24 C23 1.351(17) . ?
C33 C34 1.383(19) . ?
C5 C4 1.380(17) . ?
C29 C30 1.371(16) . ?
C34 C35 1.349(19) . ?
C20 C21 1.373(19) . ?
C23 C22 1.36(3) . ?
C21 C22 1.36(3) . ?
C12 C11 1.408(15) . ?

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
P1 Hg1 Br1 131.12(7) . . ?
P1 Hg1 I2 112.25(8) . . ?
Br1 Hg1 I2 106.10(4) . . ?
P1 Hg1 I1 101.15(7) . . ?
Br1 Hg1 I1 106.56(4) . . ?
I2 Hg1 I1 92.24(3) . . ?
P2 Hg2 Br2 128.17(8) . . ?
P2 Hg2 I1 110.40(8) . . ?
Br2 Hg2 I1 108.51(4) . . ?
P2 Hg2 I2 104.01(7) . . ?
Br2 Hg2 I2 106.40(3) . . ?
I1 Hg2 I2 93.50(3) . . ?
Hg1 I2 Hg2 87.35(3) . . ?
Hg2 I1 Hg1 86.91(3) . . ?
C19 P2 C31 107.6(6) . . ?
C19 P2 C25 107.2(5) . . ?
C31 P2 C25 106.5(5) . . ?
C19 P2 Hg2 110.9(4) . . ?
C31 P2 Hg2 113.5(3) . . ?
C25 P2 Hg2 110.7(4) . . ?
C1 P1 C7 108.7(6) . . ?
C1 P1 C13 107.8(5) . . ?
C7 P1 C13 107.8(5) . . ?
C1 P1 Hg1 111.8(3) . . ?
C7 P1 Hg1 109.4(3) . . ?
C13 P1 Hg1 111.3(4) . . ?
C24 C19 C20 119.0(13) . . ?
C24 C19 P2 123.0(11) . . ?
C20 C19 P2 117.9(11) . . ?
C36 C31 C32 118.8(11) . . ?
C36 C31 P2 122.8(9) . . ?
C32 C31 P2 118.3(8) . . ?
C26 C25 C30 117.5(11) . . ?
C26 C25 P2 122.7(9) . . ?
C30 C25 P2 119.7(9) . . ?
C5 C6 C1 121.1(11) . . ?
C6 C1 C2 118.0(11) . . ?
C6 C1 P1 122.5(8) . . ?
C2 C1 P1 119.5(8) . . ?
C18 C13 C14 119.9(10) . . ?
C18 C13 P1 119.3(8) . . ?
C14 C13 P1 120.6(8) . . ?
C13 C14 C15 119.7(11) . . ?
C3 C2 C1 120.9(11) . . ?
C12 C7 C8 119.9(12) . . ?
C12 C7 P1 118.4(9) . . ?
C8 C7 P1 121.7(11) . . ?
C33 C32 C31 120.5(13) . . ?
C29 C28 C27 122.2(12) . . ?
C16 C15 C14 117.9(12) . . ?
C26 C27 C28 117.5(12) . . ?
C25 C26 C27 122.2(12) . . ?
C10 C9 C8 115.4(14) . . ?
C9 C10 C11 127.5(16) . . ?
C2 C3 C4 121.0(12) . . ?
C16 C17 C18 120.2(13) . . ?
C31 C36 C35 119.9(13) . . ?
C23 C24 C19 118.3(17) . . ?
C32 C33 C34 119.7(15) . . ?
C17 C16 C15 122.4(12) . . ?
C7 C8 C9 118.9(14) . . ?
C6 C5 C4 120.8(12) . . ?
C28 C29 C30 118.2(13) . . ?
C35 C34 C33 121.3(16) . . ?
C21 C20 C19 120.4(17) . . ?
C24 C23 C22 124(2) . . ?
C22 C21 C20 120(2) . . ?
C21 C22 C23 117.9(18) . . ?
C25 C30 C29 122.3(12) . . ?
C7 C12 C11 121.8(13) . . ?
C13 C18 C17 119.7(12) . . ?
C5 C4 C3 118.2(13) . . ?
C10 C11 C12 116.5(15) . . ?
C34 C35 C36 119.9(15) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         1.309
_refine_diff_density_min         -0.756
_refine_diff_density_rms         0.154


####################################################################### 
# 
# 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_preex1_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2086290'
loop_
_audit_author_name
_audit_author_address
'Emanuele Priola'
;University of Turin
Italy
;
_audit_update_record             
;
2021-05-27 deposited with the CCDC.	2022-03-07 downloaded from the CCDC.
;
_audit_creation_date             2020-07-03
_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         'C10 H8 Br Hg I N2'
_chemical_formula_sum            'C10 H8 Br Hg I N2'
_chemical_formula_weight         563.58
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
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'
Hg Hg -2.3894 9.2266 '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                   8.6933(5)
_cell_length_b                   9.1875(7)
_cell_length_c                   9.4039(8)
_cell_angle_alpha                118.877(8)
_cell_angle_beta                 102.032(6)
_cell_angle_gamma                96.897(5)
_cell_volume                     621.51(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2967
_cell_measurement_temperature    299
_cell_measurement_theta_max      24.4420
_cell_measurement_theta_min      3.4820
_shelx_estimated_absorpt_T_max   0.293
_shelx_estimated_absorpt_T_min   0.173
_exptl_absorpt_coefficient_mu    18.049
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51775
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    3.012
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             500
_exptl_crystal_size_max          0.15
_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  0.0787
_diffrn_reflns_av_unetI/netI     0.0664
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            17090
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.507
_diffrn_reflns_theta_min         3.471
_diffrn_ambient_temperature      299
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1990
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     20.00  46.00   1.00   25.00    --  -29.89  17.00-141.00   26
  2  ω    -27.00  -1.00   1.00   25.00    --  -29.89  17.00-141.00   26
  3  ω     64.00 112.00   1.00   25.00    --   31.14  17.00-141.00   48
  4  ω     32.00  61.00   1.00   25.00    --   31.14  17.00-141.00   29
  5  ω    -67.00 -19.00   1.00   25.00    --  -29.89 -17.00  49.00   48
  6  ω   -109.00 -79.00   1.00   25.00    --  -29.89 -17.00  49.00   30
  7  ω    -50.00 -10.00   1.00   25.00    --   31.14 -17.00  49.00   40
  8  ω    -43.00  62.00   1.00   25.00    --   31.14 -70.00-103.46  105
  9  ω      2.00 103.00   1.00   25.00    --   31.14  67.00  11.98  101
 10  ω    -43.00  62.00   1.00   25.00    --   31.14 -70.00  -1.75  105
 11  ω    -33.00  62.00   1.00   25.00    --   31.14 -70.00 167.23   95
 12  ω    -38.00  61.00   1.00   25.00    --   31.14 -70.00  94.35   99
 13  ω      0.00  49.00   1.00   25.00    --   31.14  70.00-136.82   49
 14  ω     65.00  98.00   1.00   25.00    --   31.14  70.00-136.82   33
 15  ω      6.00 105.00   1.00   25.00    --   31.14  70.00 101.31   99
 16  ω      1.00 105.00   1.00   25.00    --   31.14  69.00 -68.85  104
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, AtlasS2, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0143977000
_diffrn_orient_matrix_UB_12      0.0091451000
_diffrn_orient_matrix_UB_13      0.0813254000
_diffrn_orient_matrix_UB_21      -0.0147388000
_diffrn_orient_matrix_UB_22      -0.0905390000
_diffrn_orient_matrix_UB_23      -0.0389207000
_diffrn_orient_matrix_UB_31      0.0838476000
_diffrn_orient_matrix_UB_32      0.0067352000
_diffrn_orient_matrix_UB_33      0.0077551000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2274
_reflns_number_total             3784
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.44
_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 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         1.070
_refine_diff_density_min         -1.178
_refine_diff_density_rms         0.181
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         3784
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0944
_refine_ls_R_factor_gt           0.0436
_refine_ls_restrained_S_all      1.011
_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)+(0.0239P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0731
_refine_ls_wR_factor_ref         0.0889
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Others
 Sof(I1B)=Sof(Br1B)=1-FVAR(1)
 Sof(I1A)=Sof(Br1A)=FVAR(1)
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C8(H8), C1(H1), C7(H7), C9(H9), C10(H10), C3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     heavy
_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
Hg1 Hg 0.71059(4) 0.74135(5) 0.65311(5) 0.05681(13) Uani 1 1 d . . . . .
I1A I 0.9797(4) 0.6961(5) 0.7891(5) 0.0666(10) Uani 0.809(5) 1 d . . P A 1
Br1A Br 0.4355(4) 0.6591(4) 0.6959(5) 0.0491(8) Uani 0.809(5) 1 d . . P A 1
C5 C 0.7610(8) 0.9566(10) 0.4696(10) 0.0425(18) Uani 1 1 d . . . . .
N2 N 0.7670(7) 0.8016(8) 0.4497(9) 0.0443(15) Uani 1 1 d . . . . .
C6 C 0.7106(8) 1.0771(9) 0.6173(9) 0.0373(16) Uani 1 1 d . . . . .
N1 N 0.6811(7) 1.0219(8) 0.7201(9) 0.0451(15) Uani 1 1 d . . . . .
C2 C 0.8632(10) 0.7306(12) 0.2102(12) 0.063(3) Uani 1 1 d . . . . .
H2 H 0.900577 0.652984 0.125333 0.076 Uiso 1 1 calc R . . . .
C4 C 0.8044(9) 1.0021(10) 0.3606(10) 0.0482(19) Uani 1 1 d . . . . .
H4 H 0.801858 1.110123 0.377436 0.058 Uiso 1 1 calc R . . . .
C8 C 0.6423(10) 1.3360(11) 0.7828(12) 0.058(2) Uani 1 1 d . . . . .
H8 H 0.629835 1.442880 0.803097 0.070 Uiso 1 1 calc R . . . .
C1 C 0.8172(9) 0.6952(11) 0.3245(12) 0.053(2) Uani 1 1 d . . . . .
H1 H 0.821982 0.589290 0.312293 0.064 Uiso 1 1 calc R . . . .
C7 C 0.6938(9) 1.2322(10) 0.6455(11) 0.050(2) Uani 1 1 d . . . . .
H7 H 0.716321 1.268989 0.573961 0.060 Uiso 1 1 calc R . . . .
C9 C 0.6102(10) 1.2820(11) 0.8873(12) 0.059(2) Uani 1 1 d . . . . .
H9 H 0.574216 1.349278 0.978816 0.071 Uiso 1 1 calc R . . . .
C10 C 0.6328(10) 1.1239(12) 0.8526(11) 0.056(2) Uani 1 1 d . . . . .
H10 H 0.613757 1.086198 0.924556 0.068 Uiso 1 1 calc R . . . .
C3 C 0.8512(10) 0.8886(12) 0.2279(12) 0.062(2) Uani 1 1 d . . . . .
H3 H 0.874688 0.916049 0.150361 0.075 Uiso 1 1 calc R . . . .
I1B I 0.4390(15) 0.6674(18) 0.7064(18) 0.092(4) Uani 0.191(5) 1 d . . P A 2
Br1B Br 0.996(2) 0.711(3) 0.816(3) 0.037(2) Uani 0.191(5) 1 d . . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Hg1 I1A 2.605(4) . ?
Hg1 Br1A 2.591(3) . ?
Hg1 N2 2.356(6) . ?
Hg1 N1 2.401(6) . ?
Hg1 I1B 2.593(12) . ?
Hg1 Br1B 2.750(19) . ?
C5 N2 1.354(9) . ?
C5 C6 1.494(11) . ?
C5 C4 1.380(10) . ?
N2 C1 1.319(10) . ?
C6 N1 1.342(8) . ?
C6 C7 1.350(9) . ?
N1 C10 1.339(10) . ?
C2 C1 1.381(11) . ?
C2 C3 1.399(12) . ?
C4 C3 1.366(11) . ?
C8 C7 1.389(11) . ?
C8 C9 1.358(12) . ?
C9 C10 1.376(11) . ?

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
Br1A Hg1 I1A 123.10(9) . . ?
N2 Hg1 I1A 104.96(16) . . ?
N2 Hg1 Br1A 130.39(16) . . ?
N2 Hg1 N1 69.2(2) . . ?
N2 Hg1 I1B 131.5(3) . . ?
N2 Hg1 Br1B 106.6(3) . . ?
N1 Hg1 I1A 121.94(17) . . ?
N1 Hg1 Br1A 92.76(16) . . ?
N1 Hg1 I1B 91.9(3) . . ?
N1 Hg1 Br1B 119.4(4) . . ?
I1B Hg1 Br1B 121.3(4) . . ?
N2 C5 C6 117.0(6) . . ?
N2 C5 C4 121.1(8) . . ?
C4 C5 C6 121.9(7) . . ?
C5 N2 Hg1 119.1(5) . . ?
C1 N2 Hg1 122.3(5) . . ?
C1 N2 C5 118.3(7) . . ?
N1 C6 C5 116.3(6) . . ?
N1 C6 C7 121.6(8) . . ?
C7 C6 C5 122.1(7) . . ?
C6 N1 Hg1 118.4(5) . . ?
C10 N1 Hg1 123.0(5) . . ?
C10 N1 C6 118.5(7) . . ?
C1 C2 C3 117.0(9) . . ?
C3 C4 C5 120.0(8) . . ?
C9 C8 C7 120.2(8) . . ?
N2 C1 C2 124.3(8) . . ?
C6 C7 C8 119.2(8) . . ?
C8 C9 C10 117.4(9) . . ?
N1 C10 C9 123.0(8) . . ?
C4 C3 C2 119.2(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 1.712
_oxdiff_exptl_absorpt_empirical_full_min 0.754
####################################################################### 
# 
# 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_preex1_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 2086283'
loop_
_audit_author_name
_audit_author_address
'Emanuele Priola'
;University of Turin
Italy
;
_audit_update_record             
;
2021-05-27 deposited with the CCDC.	2022-03-07 downloaded from the CCDC.
;
_audit_creation_date             2020-11-25
_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         'C12 H8 Br2 Hg N2'
_chemical_formula_sum            'C12 H8 Br2 Hg N2'
_chemical_formula_weight         540.61
_chemical_melting_point          ?
_chemical_oxdiff_formula         'Hg Br2 N2 C12 H8'
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'
Hg Hg -2.3894 9.2266 '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                   7.885(4)
_cell_length_b                   9.159(4)
_cell_length_c                   9.703(2)
_cell_angle_alpha                92.36(3)
_cell_angle_beta                 112.06(4)
_cell_angle_gamma                101.02(4)
_cell_volume                     632.6(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    450
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      19.3930
_cell_measurement_theta_min      3.8990
_shelx_estimated_absorpt_T_max   0.526
_shelx_estimated_absorpt_T_min   0.198
_exptl_absorpt_coefficient_mu    18.459
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.22228
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.838
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0805
_diffrn_reflns_av_unetI/netI     0.2889
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4931
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         3.237
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1990
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -91.00   7.00   1.00   55.00    --  -18.30 -68.00 -19.51   98
  2  ω    -42.00  53.00   1.00   55.00    --  -18.30  57.00 120.00   95
  3  ω    -76.00  -7.00   1.00   55.00    --  -18.30 -68.00-112.10   69
  4  ω      5.00  49.00   1.00   55.00    --   19.55  70.00-168.32   44
  5  ω    -41.00  21.00   1.00   55.00    --   19.55 -57.00-150.00   62
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, AtlasS2, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0848038000
_diffrn_orient_matrix_UB_12      0.0298824000
_diffrn_orient_matrix_UB_13      -0.0086344000
_diffrn_orient_matrix_UB_21      -0.0025298000
_diffrn_orient_matrix_UB_22      -0.0714070000
_diffrn_orient_matrix_UB_23      -0.0329147000
_diffrn_orient_matrix_UB_31      -0.0521040000
_diffrn_orient_matrix_UB_32      0.0181980000
_diffrn_orient_matrix_UB_33      -0.0718335000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1871
_reflns_number_total             2581
_reflns_odcompleteness_completeness 99.77
_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 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         4.235
_refine_diff_density_min         -2.481
_refine_diff_density_rms         0.413
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2581
_refine_ls_number_restraints     212
_refine_ls_R_factor_all          0.0852
_refine_ls_R_factor_gt           0.0518
_refine_ls_restrained_S_all      0.983
_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)+(0.1452P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1079
_refine_ls_wR_factor_ref         0.1137
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 C6-C7
 1.35 with sigma of 0.02
 C6-C5
 1.35 with sigma of 0.02
 C3-C4
 1.35 with sigma of 0.02
 C3-C2
 1.35 with sigma of 0.02
 C7-C11
 1.35 with sigma of 0.02
3. Rigid bond restraints
 C1, C2, C3
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C1, N1, C12, C4, C5, C6, C7, C11, N2, C10, C9, C8
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
C1 \\sim C2 \\sim C3: within 1.7A with sigma of 0.004 and sigma for terminal
atoms of 0.008
C1 \\sim N1 \\sim C12 \\sim C4 \\sim C5 \\sim C6 \\sim C7 \\sim C11 \\sim N2
\\sim C10 \\sim C9 \\sim C8: within 1.7A with sigma of 0.04 and sigma for
terminal atoms of 0.08
Uanis(C1) \\sim Ueq, Uanis(N1) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(C3) \\sim
Ueq, Uanis(C4) \\sim Ueq, Uanis(C12) \\sim Ueq, Uanis(C11) \\sim Ueq, Uanis(C7)
\\sim Ueq, Uanis(C8) \\sim Ueq, Uanis(C9) \\sim Ueq, Uanis(C10) \\sim Ueq,
Uanis(N2) \\sim Ueq, Uanis(C6) \\sim Ueq, Uanis(C5) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.02
Uanis(N1) \\sim Ueq, Uanis(C1) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(C3) \\sim
Ueq, Uanis(C4) \\sim Ueq, Uanis(C12) \\sim Ueq, Uanis(C11) \\sim Ueq, Uanis(N2)
\\sim Ueq, Uanis(C10) \\sim Ueq, Uanis(C9) \\sim Ueq, Uanis(C8) \\sim Ueq,
Uanis(C7) \\sim Ueq, Uanis(C6) \\sim Ueq, Uanis(C5) \\sim Ueq: with sigma of
0.1 and sigma for terminal atoms of 0.2
Uanis(C2) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
5.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C1(H1), C8(H8), C3(H3), C6(H6), C2(H2), C9(H9), C5(H5)
;
_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
Hg1 Hg 0.0134(2) 0.2367(2) 0.37246(19) 0.0800(9) Uani 1 1 d . . . . .
Br2 Br -0.2475(6) 0.3512(5) 0.3827(5) 0.0698(14) Uani 1 1 d . . . . .
Br1 Br 0.2776(6) 0.1446(5) 0.5510(5) 0.0784(15) Uani 1 1 d . . . . .
N2 N -0.130(4) 0.095(3) 0.128(4) 0.052(6) Uani 1 1 d . U . . .
N1 N 0.141(3) 0.350(3) 0.213(3) 0.042(5) Uani 1 1 d . U . . .
C10 C -0.275(5) -0.031(4) 0.073(5) 0.060(7) Uani 1 1 d . U . . .
H10 H -0.312758 -0.078944 0.143050 0.072 Uiso 1 1 calc R . . . .
C1 C 0.264(4) 0.457(4) 0.236(4) 0.044(4) Uani 1 1 d . U . . .
H1 H 0.317647 0.495601 0.336779 0.053 Uiso 1 1 calc R . . . .
C11 C -0.087(4) 0.173(4) 0.013(3) 0.044(5) Uani 1 1 d D U . . .
C12 C 0.048(5) 0.296(4) 0.056(4) 0.049(5) Uani 1 1 d . U . . .
C8 C -0.302(4) -0.006(3) -0.169(4) 0.042(5) Uani 1 1 d . U . . .
H8 H -0.363203 -0.045463 -0.269563 0.050 Uiso 1 1 calc R . . . .
C3 C 0.272(4) 0.497(3) 0.006(3) 0.044(5) Uani 1 1 d D U . . .
H3 H 0.317319 0.549204 -0.058514 0.053 Uiso 1 1 calc R . . . .
C4 C 0.125(4) 0.375(3) -0.048(4) 0.042(5) Uani 1 1 d D U . . .
C7 C -0.171(4) 0.122(3) -0.139(3) 0.039(5) Uani 1 1 d D U . . .
C6 C -0.114(4) 0.190(3) -0.245(4) 0.049(6) Uani 1 1 d D U . . .
H6 H -0.165028 0.149204 -0.345238 0.058 Uiso 1 1 calc R . . . .
C2 C 0.349(4) 0.540(4) 0.153(3) 0.044(4) Uani 1 1 d D U . . .
H2 H 0.451552 0.620216 0.197764 0.053 Uiso 1 1 calc R . . . .
C9 C -0.362(5) -0.089(4) -0.065(5) 0.054(6) Uani 1 1 d . U . . .
H9 H -0.454271 -0.177474 -0.094873 0.065 Uiso 1 1 calc R . . . .
C5 C 0.020(4) 0.318(3) -0.195(4) 0.052(6) Uani 1 1 d D U . . .
H5 H 0.043198 0.372455 -0.267523 0.062 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
Hg1 Br2 2.512(5) . ?
Hg1 Br1 2.477(4) . ?
Hg1 N2 2.40(3) . ?
Hg1 N1 2.33(3) . ?
N2 C10 1.38(4) . ?
N2 C11 1.46(4) . ?
N1 C1 1.18(3) . ?
N1 C12 1.43(4) . ?
C10 C9 1.29(5) . ?
C1 C2 1.39(5) . ?
C11 C12 1.32(4) . ?
C11 C7 1.385(19) . ?
C12 C4 1.51(5) . ?
C8 C7 1.35(4) . ?
C8 C9 1.46(5) . ?
C3 C4 1.372(18) . ?
C3 C2 1.337(19) . ?
C4 C5 1.37(5) . ?
C7 C6 1.392(19) . ?
C6 C5 1.344(18) . ?

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
Br1 Hg1 Br2 137.08(17) . . ?
N2 Hg1 Br2 101.9(7) . . ?
N2 Hg1 Br1 114.2(7) . . ?
N1 Hg1 Br2 111.1(6) . . ?
N1 Hg1 Br1 102.9(6) . . ?
N1 Hg1 N2 69.8(10) . . ?
C10 N2 Hg1 130(3) . . ?
C10 N2 C11 115(3) . . ?
C11 N2 Hg1 113.8(19) . . ?
C1 N1 Hg1 131(3) . . ?
C1 N1 C12 112(3) . . ?
C12 N1 Hg1 117(2) . . ?
C9 C10 N2 126(4) . . ?
N1 C1 C2 137(4) . . ?
C12 C11 N2 118(3) . . ?
C12 C11 C7 118(3) . . ?
C7 C11 N2 124(3) . . ?
N1 C12 C4 117(3) . . ?
C11 C12 N1 119(4) . . ?
C11 C12 C4 123(3) . . ?
C7 C8 C9 128(3) . . ?
C2 C3 C4 118(3) . . ?
C3 C4 C12 120(3) . . ?
C5 C4 C12 112(3) . . ?
C5 C4 C3 127(3) . . ?
C11 C7 C6 123(3) . . ?
C8 C7 C11 112(3) . . ?
C8 C7 C6 125(3) . . ?
C5 C6 C7 117(3) . . ?
C3 C2 C1 115(3) . . ?
C10 C9 C8 114(4) . . ?
C6 C5 C4 126(3) . . ?


_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 2.536
_oxdiff_exptl_absorpt_empirical_full_min 0.569
####################################################################### 
# 
# 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_exp_103
_database_code_depnum_ccdc_archive 'CCDC 2086292'
loop_
_audit_author_name
_audit_author_address
'Emanuele Priola'
;University of Turin
Italy
;
_audit_update_record             
;
2021-05-27 deposited with the CCDC.	2022-03-07 downloaded from the CCDC.
;
_audit_creation_date             2020-07-01
_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         '0.5(Br2 Hg2 I2)'
_chemical_formula_sum            'Br Hg I'
_chemical_formula_weight         407.40
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Hg Hg -2.3894 9.2266 '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'

_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           36
_space_group_name_H-M_alt        'C m c 21'
_space_group_name_Hall           'C 2c -2'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, 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'
'-x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   4.6018(10)
_cell_length_b                   6.8966(12)
_cell_length_c                   12.648(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     401.40(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    619
_cell_measurement_temperature    200.00(10)
_cell_measurement_theta_max      28.2190
_cell_measurement_theta_min      5.3340
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    55.735
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.16884
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (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_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    6.741
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0883
_diffrn_reflns_av_unetI/netI     0.0666
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            1784
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.365
_diffrn_reflns_theta_min         4.835
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      200.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1990
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -32.00  31.00   1.00   15.00    --  -10.13  24.00 101.00   63
  2  ω    -56.00 -31.00   1.00   15.00    --  -10.13 -24.00 -62.00   25
  3  ω    -53.00  45.00   1.00   15.00    --   11.30 -24.00 -62.00   98
  4  ω      9.00  35.00   1.00   15.00    --   11.30  24.00 101.00   26
  5  ω    -38.00  29.00   1.00   15.00    --  -10.13  57.00 150.00   67
  6  ω    -41.00 -14.00   1.00   15.00    --  -10.13  70.00  24.62   27
  7  ω    -13.00  45.00   1.00   15.00    --   11.30  37.00 -30.00   58
  8  ω     -9.00  17.00   1.00   15.00    --   11.30  57.00   0.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, AtlasS2, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1390181000
_diffrn_orient_matrix_UB_12      0.0319799000
_diffrn_orient_matrix_UB_13      -0.0167305000
_diffrn_orient_matrix_UB_21      -0.0548985000
_diffrn_orient_matrix_UB_22      0.0955327000
_diffrn_orient_matrix_UB_23      -0.0061227000
_diffrn_orient_matrix_UB_31      0.0375162000
_diffrn_orient_matrix_UB_32      0.0211076000
_diffrn_orient_matrix_UB_33      0.0531409000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.888
_reflns_Friedel_fraction_full    0.984
_reflns_Friedel_fraction_max     0.977
_reflns_number_gt                412
_reflns_number_total             457
_reflns_odcompleteness_completeness 98.87
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         3.944
_refine_diff_density_min         -2.894
_refine_diff_density_rms         0.651
_refine_ls_abs_structure_details 
;
 Flack x determined using 160 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_hydrogen_treatment    undef
_refine_ls_matrix_type           full
_refine_ls_number_parameters     20
_refine_ls_number_reflns         457
_refine_ls_number_restraints     37
_refine_ls_R_factor_all          0.0725
_refine_ls_R_factor_gt           0.0649
_refine_ls_restrained_S_all      1.070
_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)+(0.0875P)²+48.9439P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1690
_refine_ls_wR_factor_ref         0.1754
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.90(10)
 0.10(10)
2. Shared sites
{Br1A, I2A}
{I1A, Br2A}
3. Rigid bond restraints
 Br1A, Hg1, Br2A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 Hg1, I2A, Br1A, Br2A, I1A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
4. Uiso/Uaniso restraints and constraints
Br1A \\sim Hg1 \\sim Br2A: within 1.7A with sigma of 0.04 and sigma for
terminal atoms of 0.08
Hg1 \\sim I2A \\sim Br1A \\sim Br2A \\sim I1A: within 1.7A with sigma of 0.004
and sigma for terminal atoms of 0.008
Uanis(Br1A) \\sim Ueq, Uanis(Hg1) \\sim Ueq, Uanis(Br2A) \\sim Ueq: with sigma
of 0.1 and sigma for terminal atoms of 0.2
Uanis(Br2A) = Uanis(I1A)
Uanis(Br1A) = Uanis(I2A)
Uanis(I1A) = Uanis(Br2A)
5. Others
 Fixed Sof: I1A(0.25) Br1A(0.25) Br2A(0.25) I2A(0.25)
;
_atom_sites_solution_hydrogens   .
_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
Hg1 Hg 0.000000 -0.6663(4) -0.2336(4) 0.0339(8) Uani 1 2 d S TU P . .
I1A I 0.000000 -0.3999(9) -0.3649(4) 0.0393(15) Uani 0.5 2 d S TU P A 1
Br1A Br 0.000000 -0.9340(9) -0.1028(4) 0.0413(15) Uani 0.5 2 d S TU P A 1
Br2A Br 0.000000 -0.3999(9) -0.3649(4) 0.0393(15) Uani 0.25 1 d S TU P A -1
I2A I 0.000000 -0.9340(9) -0.1028(4) 0.0413(15) Uani 0.25 1 d S TU P A -1


_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
Hg1 I1A 3.263(5) 5_545 ?
Hg1 I1A 3.263(5) 5_445 ?
Hg1 I1A 2.477(6) . ?
Hg1 Br1A 2.478(6) . ?
Hg1 Br2A 2.477(6) . ?
Hg1 I2A 2.478(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
I1A Hg1 I1A 89.70(17) 5_445 5_545 ?
I1A Hg1 I1A 91.44(16) . 5_445 ?
I1A Hg1 I1A 91.44(16) . 5_545 ?
I1A Hg1 Br1A 179.8(3) . . ?
I1A Hg1 I2A 179.8(3) . . ?
Br1A Hg1 I1A 88.39(14) . 5_545 ?
Br1A Hg1 I1A 88.39(14) . 5_445 ?
Br2A Hg1 I1A 91.44(16) . 5_445 ?
Br2A Hg1 I1A 91.44(16) . 5_545 ?
Br2A Hg1 I1A 0.0 . . ?
Br2A Hg1 Br1A 179.8(3) . . ?
Br2A Hg1 I2A 179.8(3) . . ?
I2A Hg1 I1A 88.39(14) . 5_545 ?
I2A Hg1 I1A 88.39(14) . 5_445 ?
I2A Hg1 Br1A 0.0 . . ?
Hg1 I1A Hg1 89.69(17) 5 5_455 ?
Hg1 I1A Hg1 91.44(16) . 5 ?
Hg1 I1A Hg1 91.44(16) . 5_455 ?

_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 2.808
_oxdiff_exptl_absorpt_empirical_full_min 0.421
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.90(10)
2 0.10(10)

####################################################################### 
# 
# 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_exp1
_database_code_depnum_ccdc_archive 'CCDC 2086284'
loop_
_audit_author_name
_audit_author_address
'Emanuele Priola'
;University of Turin
Italy
;
_audit_update_record             
;
2021-10-26 deposited with the CCDC.	2022-03-07 downloaded from the CCDC.
;
_audit_creation_date             2021-10-19
_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         'C15 H11 Br Hg I N3'
_chemical_formula_sum            'C15 H11 Br Hg I N3'
_chemical_formula_weight         640.67
_chemical_melting_point          ?
_chemical_oxdiff_formula         'Hg Br I C15 N3'
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'
Hg Hg -2.3894 9.2266 '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        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   14.2230(7)
_cell_length_b                   9.7175(3)
_cell_length_c                   11.9627(5)
_cell_angle_alpha                90
_cell_angle_beta                 95.902(4)
_cell_angle_gamma                90
_cell_volume                     1644.61(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3090
_cell_measurement_temperature    298.00
_cell_measurement_theta_max      27.2580
_cell_measurement_theta_min      3.7950
_shelx_estimated_absorpt_T_max   0.408
_shelx_estimated_absorpt_T_min   0.291
_exptl_absorpt_coefficient_mu    13.661
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49644
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.587
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1160
_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  0.0403
_diffrn_reflns_av_unetI/netI     0.0277
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7813
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         3.424
_diffrn_ambient_temperature      298.00
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.2890
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -105.00  50.00   1.00   75.00    --  -38.17   0.00  60.00  155
  2  ω    -86.00  -8.00   1.00   75.00    --  -38.17 -70.00-118.45   78
  3  ω    -49.00 -14.00   1.00   75.00    --  -38.17 -37.00 -30.00   35
  4  ω   -106.00 -80.00   1.00   75.00    --  -38.17 -37.00 -30.00   26
  5  ω   -108.00  -8.00   1.00   75.00    --  -38.17 -69.00 -44.96  100
  6  ω    -69.00  22.00   1.00   75.00    --  -38.17  70.00  98.84   91
  7  ω     85.00 106.00   1.00   75.00    --   38.17  70.00-119.94   21
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0225317000
_diffrn_orient_matrix_UB_12      -0.0626133000
_diffrn_orient_matrix_UB_13      -0.0176181000
_diffrn_orient_matrix_UB_21      0.0428091000
_diffrn_orient_matrix_UB_22      -0.0240676000
_diffrn_orient_matrix_UB_23      -0.0186799000
_diffrn_orient_matrix_UB_31      0.0131951000
_diffrn_orient_matrix_UB_32      -0.0288072000
_diffrn_orient_matrix_UB_33      0.0537726000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1480
_reflns_number_total             1684
_reflns_odcompleteness_completeness 99.66
_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 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         1.159
_refine_diff_density_min         -0.751
_refine_diff_density_rms         0.120
_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     97
_refine_ls_number_reflns         1684
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0365
_refine_ls_R_factor_gt           0.0303
_refine_ls_restrained_S_all      1.050
_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)+(0.0340P)²+3.3739P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0692
_refine_ls_wR_factor_ref         0.0725
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Shared sites
{I1, Br1}
3. Uiso/Uaniso restraints and constraints
Uanis(I1) = Uanis(Br1)
4. Others
 Fixed Sof: I1(0.5) Br1(0.5)
5.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C1(H1), C4(H4), C7(H7), C8(H8), C3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     heavy
_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
Hg1 Hg 0.750000 0.48342(3) 0.000000 0.05391(14) Uani 1 2 d S T P . .
I1 I 0.61876(4) 0.35205(6) 0.10186(5) 0.06791(18) Uani 0.5 1 d . . . A 1
N1 N 0.8426(4) 0.5796(6) 0.1635(4) 0.0558(12) Uani 1 1 d . . . . .
N2 N 0.750000 0.7344(7) 0.000000 0.0498(16) Uani 1 2 d S T P A .
C5 C 0.8482(4) 0.7175(6) 0.1754(5) 0.0516(14) Uani 1 1 d . . . . .
C6 C 0.7975(4) 0.8018(6) 0.0847(5) 0.0525(14) Uani 1 1 d . . . . .
C2 C 0.9389(5) 0.5472(10) 0.3356(6) 0.077(2) Uani 1 1 d . . . . .
H2 H 0.968939 0.488064 0.389002 0.092 Uiso 1 1 calc R . . . .
C1 C 0.8872(5) 0.4967(8) 0.2413(6) 0.0688(19) Uani 1 1 d . . . . .
H1 H 0.882860 0.401987 0.231155 0.083 Uiso 1 1 calc R . . . .
C4 C 0.8998(5) 0.7731(8) 0.2686(6) 0.072(2) Uani 1 1 d . . . . .
H4 H 0.903976 0.868044 0.277333 0.087 Uiso 1 1 calc R . . . .
C7 C 0.7987(5) 0.9449(7) 0.0879(7) 0.0694(19) Uani 1 1 d . . . . .
H7 H 0.831413 0.991975 0.147500 0.083 Uiso 1 1 calc R . . . .
C8 C 0.750000 1.0145(10) 0.000000 0.082(4) Uani 1 2 d S T P . .
H8 H 0.749999 1.110162 0.000001 0.098 Uiso 1 2 calc RS T P . .
C3 C 0.9453(5) 0.6870(11) 0.3490(6) 0.084(2) Uani 1 1 d . . . . .
H3 H 0.980148 0.724005 0.411924 0.101 Uiso 1 1 calc R . . . .
Br1 Br 0.61876(4) 0.35205(6) 0.10186(5) 0.06791(18) Uani 0.5 1 d . . . A -1


_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
Hg1 I1 2.6583(6) 2_655 ?
Hg1 I1 2.6583(6) . ?
Hg1 N1 2.430(5) . ?
Hg1 N1 2.430(5) 2_655 ?
Hg1 N2 2.439(7) . ?
Hg1 Br1 2.6583(6) . ?
N1 C5 1.349(8) . ?
N1 C1 1.340(9) . ?
N2 C6 1.331(7) . ?
N2 C6 1.331(7) 2_655 ?
C5 C6 1.485(9) . ?
C5 C4 1.380(8) . ?
C6 C7 1.391(8) . ?
C2 C1 1.373(11) . ?
C2 C3 1.370(12) . ?
C4 C3 1.384(11) . ?
C7 C8 1.376(9) . ?

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 Hg1 I1 122.60(3) . 2_655 ?
I1 Hg1 Br1 0.0 . . ?
N1 Hg1 I1 101.87(12) 2_655 . ?
N1 Hg1 I1 101.87(12) . 2_655 ?
N1 Hg1 I1 99.44(12) 2_655 2_655 ?
N1 Hg1 I1 99.43(12) . . ?
N1 Hg1 N1 134.7(3) . 2_655 ?
N1 Hg1 N2 67.37(13) . . ?
N1 Hg1 N2 67.36(13) 2_655 . ?
N1 Hg1 Br1 99.43(12) . . ?
N1 Hg1 Br1 101.87(12) 2_655 . ?
N2 Hg1 I1 118.699(14) . 2_655 ?
N2 Hg1 I1 118.699(14) . . ?
N2 Hg1 Br1 118.699(14) . . ?
Br1 Hg1 I1 122.60(3) . 2_655 ?
C5 N1 Hg1 119.3(4) . . ?
C1 N1 Hg1 120.4(5) . . ?
C1 N1 C5 120.3(6) . . ?
C6 N2 Hg1 119.5(4) 2_655 . ?
C6 N2 Hg1 119.5(4) . . ?
C6 N2 C6 121.0(8) . 2_655 ?
N1 C5 C6 116.8(5) . . ?
N1 C5 C4 119.7(6) . . ?
C4 C5 C6 123.5(6) . . ?
N2 C6 C5 117.1(5) . . ?
N2 C6 C7 121.1(7) . . ?
C7 C6 C5 121.8(6) . . ?
C3 C2 C1 118.3(8) . . ?
N1 C1 C2 122.1(7) . . ?
C5 C4 C3 119.8(7) . . ?
C8 C7 C6 117.8(8) . . ?
C7 C8 C7 121.2(10) 2_655 . ?
C2 C3 C4 119.8(7) . . ?


_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 1.819
_oxdiff_exptl_absorpt_empirical_full_min 0.783
####################################################################### 
# 
# 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_preex2
_database_code_depnum_ccdc_archive 'CCDC 2086286'
loop_
_audit_author_name
_audit_author_address
'Emanuele Priola'
;University of Turin
Italy
;
_audit_update_record             
;
2021-10-26 deposited with the CCDC.	2022-03-07 downloaded from the CCDC.
;
_audit_creation_date             2021-10-20
_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         'C10 H8 Br Hg I N2'
_chemical_formula_sum            'C10 H8 Br Hg I N2'
_chemical_formula_weight         563.58
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'Hg Br I C10 N2'
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'
Hg Hg -2.3894 9.2266 '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           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'

_cell_length_a                   8.6880(4)
_cell_length_b                   9.1908(5)
_cell_length_c                   9.3998(6)
_cell_angle_alpha                118.781(6)
_cell_angle_beta                 102.005(5)
_cell_angle_gamma                96.962(4)
_cell_volume                     621.64(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3808
_cell_measurement_temperature    298.00
_cell_measurement_theta_max      27.2080
_cell_measurement_theta_min      4.0330
_shelx_estimated_absorpt_T_max   0.326
_shelx_estimated_absorpt_T_min   0.221
_exptl_absorpt_coefficient_mu    18.045
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.24474
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    3.011
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             500
_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  0.0379
_diffrn_reflns_av_unetI/netI     0.0634
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_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       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            9237
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.363
_diffrn_reflns_theta_min         3.474
_diffrn_ambient_temperature      298.00
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.2890
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -39.00  62.00   1.00   10.61    --  -10.53  57.00  60.00  101
  2  ω    -12.00  39.00   1.00   10.61    --   10.45 -57.00 -30.00   51
  3  ω    -41.00  62.00   1.00   10.61    --  -10.53  66.00 -89.76  103
  4  ω    -39.00  35.00   1.00   10.61    --  -10.53  57.00-180.00   74
  5  ω    -65.00   9.00   1.00   10.61    --  -10.53 -37.00 -30.00   74
  6  ω    -74.00  18.00   1.00   10.61    --  -10.53 -57.00 120.00   92
  7  ω    -76.00  -2.00   1.00   10.61    --  -10.53 -57.00 -90.00   74
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0015169000
_diffrn_orient_matrix_UB_12      0.0089699000
_diffrn_orient_matrix_UB_13      -0.0710863000
_diffrn_orient_matrix_UB_21      -0.0765889000
_diffrn_orient_matrix_UB_22      -0.0615017000
_diffrn_orient_matrix_UB_23      -0.0462286000
_diffrn_orient_matrix_UB_31      -0.0399530000
_diffrn_orient_matrix_UB_32      0.0666650000
_diffrn_orient_matrix_UB_33      0.0314418000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.982
_reflns_Friedel_fraction_full    0.983
_reflns_Friedel_fraction_max     0.979
_reflns_number_gt                3636
_reflns_number_total             5026
_reflns_odcompleteness_completeness 99.72
_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 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         1.805
_refine_diff_density_min         -2.135
_refine_diff_density_rms         0.228
_refine_ls_abs_structure_details 
;
 Flack x determined using 1321 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.44(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         5026
_refine_ls_number_restraints     147
_refine_ls_R_factor_all          0.0826
_refine_ls_R_factor_gt           0.0551
_refine_ls_restrained_S_all      1.040
_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)+(0.0820P)²+0.2952P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1374
_refine_ls_wR_factor_ref         0.1596
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Shared sites
{I1, Br3}
{Br1, I3}
{Br2, I4}
{Br4, I2}
3. Uiso/Uaniso restraints and constraints
Uanis(C5) \\sim Ueq, Uanis(N1) \\sim Ueq, Uanis(C1) \\sim Ueq, Uanis(C2) \\sim
Ueq, Uanis(C3) \\sim Ueq, Uanis(C4) \\sim Ueq, Uanis(C6) \\sim Ueq, Uanis(N2)
\\sim Ueq, Uanis(C10) \\sim Ueq, Uanis(C9) \\sim Ueq, Uanis(C8) \\sim Ueq,
Uanis(C7) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(N3) \\sim Ueq, Uanis(C15) \\sim Ueq, Uanis(C14) \\sim Ueq, Uanis(C13)
\\sim Ueq, Uanis(C12) \\sim Ueq, Uanis(C11) \\sim Ueq, Uanis(C16) \\sim Ueq,
Uanis(N4) \\sim Ueq, Uanis(C20) \\sim Ueq, Uanis(C19) \\sim Ueq, Uanis(C18)
\\sim Ueq, Uanis(C17) \\sim Ueq: with sigma of 0.01 and sigma for terminal
atoms of 0.02
Uanis(I1) = Uanis(Br3)
Uanis(Br1) = Uanis(I3)
Uanis(Br2) = Uanis(I4)
Uanis(Br4) = Uanis(I2)
4. Others
 Fixed Sof: I1(0.5) Br1(0.5) Br4(0.5) Br2(0.5) I3(0.5) Br3(0.5) I4(0.5) I2(0.5)
5.a Aromatic/amide H refined with riding coordinates:
 C19(H19), C17(H17), C20(H20), C18(H18), C1(H1), C11(H11), C2(H2), C13(H13),
 C4(H4), C3(H3), C14(H14), C10(H10), C7(H7), C9(H9), C8(H8), C12(H12)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     heavy
_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
Hg1 Hg 0.13726(11) 0.47762(12) 0.06865(12) 0.0610(6) Uani 1 1 d . . . . .
I1 I -0.1330(5) 0.5199(5) -0.0738(5) 0.0582(11) Uani 0.5 1 d . . P A 1
Hg2 Hg -0.44121(11) -0.04175(12) -0.62726(12) 0.0604(6) Uani 1 1 d . . . . .
Br1 Br 0.4103(6) 0.5579(6) 0.0242(7) 0.0767(14) Uani 0.5 1 d . . P A 1
Br4 Br -0.7178(5) -0.1220(6) -0.5806(5) 0.0691(12) Uani 0.5 1 d . . P B -2
Br2 Br -0.1693(5) -0.0845(6) -0.4881(5) 0.0608(11) Uani 0.5 1 d . . P B 2
N3 N -0.390(4) 0.025(4) -0.837(4) 0.048(8) Uani 1 1 d . U . . .
N4 N -0.468(5) 0.232(5) -0.571(4) 0.054(9) Uani 1 1 d . U . . .
C19 C -0.532(5) 0.497(6) -0.398(5) 0.051(10) Uani 1 1 d . U . . .
H19 H -0.563719 0.568953 -0.304163 0.061 Uiso 1 1 calc R . . . .
C17 C -0.459(7) 0.442(8) -0.639(8) 0.085(16) Uani 1 1 d . U . . .
H17 H -0.440229 0.476791 -0.713517 0.102 Uiso 1 1 calc R . . . .
C20 C -0.518(5) 0.346(6) -0.419(5) 0.055(11) Uani 1 1 d . U . . .
H20 H -0.536777 0.312821 -0.344281 0.066 Uiso 1 1 calc R . . . .
C16 C -0.440(4) 0.290(5) -0.672(5) 0.036(8) Uani 1 1 d . U . . .
C5 C 0.087(5) 0.260(6) 0.255(5) 0.048(10) Uani 1 1 d . U . . .
C15 C -0.391(5) 0.174(5) -0.807(5) 0.041(9) Uani 1 1 d . U . . .
C18 C -0.505(6) 0.556(6) -0.500(5) 0.054(10) Uani 1 1 d . U . . .
H18 H -0.516721 0.662999 -0.480222 0.065 Uiso 1 1 calc R . . . .
C1 C 0.045(5) 0.518(6) 0.398(6) 0.065(12) Uani 1 1 d . U . . .
H1 H 0.057649 0.630720 0.424032 0.078 Uiso 1 1 calc R . . . .
C11 C -0.321(4) -0.095(4) -0.956(5) 0.041(8) Uani 1 1 d . U . . .
H11 H -0.305554 -0.192841 -0.954785 0.050 Uiso 1 1 calc R . . . .
C2 C -0.003(6) 0.482(6) 0.515(6) 0.062(11) Uani 1 1 d . U . . .
H2 H -0.037674 0.559202 0.602241 0.074 Uiso 1 1 calc R . . . .
C13 C -0.292(5) 0.091(5) -1.056(5) 0.058(10) Uani 1 1 d . U . . .
H13 H -0.258762 0.118439 -1.130363 0.069 Uiso 1 1 calc R . . . .
C4 C 0.041(6) 0.215(6) 0.359(5) 0.055(11) Uani 1 1 d . U . . .
H4 H 0.035325 0.103221 0.333687 0.066 Uiso 1 1 calc R . . . .
C3 C 0.005(5) 0.312(6) 0.486(6) 0.067(11) Uani 1 1 d . U . . .
H3 H -0.016515 0.278584 0.560228 0.080 Uiso 1 1 calc R . . . .
C14 C -0.355(6) 0.215(6) -0.926(6) 0.059(11) Uani 1 1 d . U . . .
H14 H -0.370733 0.314853 -0.921822 0.071 Uiso 1 1 calc R . . . .
N1 N 0.073(4) 0.420(4) 0.268(4) 0.041(7) Uani 1 1 d . U . . .
N2 N 0.170(4) 0.191(5) -0.006(4) 0.046(8) Uani 1 1 d . U . . .
C10 C 0.214(5) 0.108(6) -0.120(5) 0.055(11) Uani 1 1 d . U . . .
H10 H 0.229737 0.151278 -0.189072 0.066 Uiso 1 1 calc R . . . .
C7 C 0.154(5) -0.021(5) 0.072(4) 0.039(8) Uani 1 1 d . U . . .
H7 H 0.129266 -0.061609 0.139664 0.046 Uiso 1 1 calc R . . . .
C6 C 0.135(5) 0.139(6) 0.095(5) 0.051(10) Uani 1 1 d . U . . .
C9 C 0.250(6) -0.067(6) -0.169(6) 0.066(13) Uani 1 1 d . U . . .
H9 H 0.290914 -0.129234 -0.257274 0.080 Uiso 1 1 calc R . . . .
C8 C 0.215(7) -0.116(7) -0.072(7) 0.076(14) Uani 1 1 d . U . . .
H8 H 0.229654 -0.222075 -0.093955 0.091 Uiso 1 1 calc R . . . .
C12 C -0.280(6) -0.059(6) -1.071(7) 0.064(11) Uani 1 1 d . U . . .
H12 H -0.244913 -0.137729 -1.157175 0.077 Uiso 1 1 calc R . . . .
I3 I 0.4103(6) 0.5579(6) 0.0242(7) 0.0767(14) Uani 0.5 1 d . . P A -1
Br3 Br -0.1330(5) 0.5199(5) -0.0738(5) 0.0582(11) Uani 0.5 1 d . . P A -1
I4 I -0.1693(5) -0.0845(6) -0.4881(5) 0.0608(11) Uani 0.5 1 d . . P B -2
I2 I -0.7178(5) -0.1220(6) -0.5806(5) 0.0691(12) Uani 0.5 1 d . . P B 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Hg1 I1 2.622(4) . ?
Hg1 Br1 2.575(4) . ?
Hg1 N1 2.32(3) . ?
Hg1 N2 2.45(3) . ?
Hg1 I3 2.575(4) . ?
Hg1 Br3 2.622(4) . ?
Hg2 Br4 2.614(4) . ?
Hg2 Br2 2.623(4) . ?
Hg2 N3 2.43(4) . ?
Hg2 N4 2.36(4) . ?
Hg2 I4 2.623(4) . ?
Hg2 I2 2.614(4) . ?
N3 C15 1.26(5) . ?
N3 C11 1.44(5) . ?
N4 C20 1.50(5) . ?
N4 C16 1.34(5) . ?
C19 C20 1.33(6) . ?
C19 C18 1.36(6) . ?
C17 C16 1.32(7) . ?
C17 C18 1.40(7) . ?
C16 C15 1.40(5) . ?
C5 C4 1.35(6) . ?
C5 N1 1.44(5) . ?
C5 C6 1.56(6) . ?
C15 C14 1.42(6) . ?
C1 C2 1.42(7) . ?
C1 N1 1.22(6) . ?
C11 C12 1.37(7) . ?
C2 C3 1.46(6) . ?
C13 C14 1.48(6) . ?
C13 C12 1.34(6) . ?
C4 C3 1.23(6) . ?
N2 C10 1.16(5) . ?
N2 C6 1.32(5) . ?
C10 C9 1.54(6) . ?
C7 C6 1.40(6) . ?
C7 C8 1.46(7) . ?
C9 C8 1.26(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
Br1 Hg1 I1 122.39(14) . . ?
Br1 Hg1 Br3 122.39(14) . . ?
N1 Hg1 I1 103.8(8) . . ?
N1 Hg1 Br1 132.4(8) . . ?
N1 Hg1 N2 71.9(11) . . ?
N1 Hg1 I3 132.4(8) . . ?
N1 Hg1 Br3 103.8(8) . . ?
N2 Hg1 I1 121.4(8) . . ?
N2 Hg1 Br1 91.4(8) . . ?
N2 Hg1 I3 91.4(8) . . ?
N2 Hg1 Br3 121.4(8) . . ?
I3 Hg1 I1 122.39(14) . . ?
I3 Hg1 Br1 0.0 . . ?
I3 Hg1 Br3 122.39(14) . . ?
Br3 Hg1 I1 0.0 . . ?
Br4 Hg2 Br2 122.96(13) . . ?
Br4 Hg2 I4 122.96(13) . . ?
Br2 Hg2 I4 0.0 . . ?
N3 Hg2 Br4 129.2(7) . . ?
N3 Hg2 Br2 106.8(7) . . ?
N3 Hg2 I4 106.8(7) . . ?
N3 Hg2 I2 129.2(7) . . ?
N4 Hg2 Br4 93.8(9) . . ?
N4 Hg2 Br2 121.8(9) . . ?
N4 Hg2 N3 65.7(11) . . ?
N4 Hg2 I4 121.8(9) . . ?
N4 Hg2 I2 93.8(9) . . ?
I2 Hg2 Br4 0.0 . . ?
I2 Hg2 Br2 122.96(13) . . ?
I2 Hg2 I4 122.96(13) . . ?
C15 N3 Hg2 117(3) . . ?
C15 N3 C11 126(4) . . ?
C11 N3 Hg2 114(2) . . ?
C20 N4 Hg2 120(3) . . ?
C16 N4 Hg2 122(3) . . ?
C16 N4 C20 118(3) . . ?
C20 C19 C18 125(4) . . ?
C16 C17 C18 125(5) . . ?
C19 C20 N4 117(4) . . ?
N4 C16 C15 113(3) . . ?
C17 C16 N4 120(4) . . ?
C17 C16 C15 127(4) . . ?
C4 C5 N1 122(4) . . ?
C4 C5 C6 125(4) . . ?
N1 C5 C6 113(3) . . ?
N3 C15 C16 122(3) . . ?
N3 C15 C14 117(4) . . ?
C16 C15 C14 120(4) . . ?
C19 C18 C17 115(4) . . ?
N1 C1 C2 128(5) . . ?
C12 C11 N3 117(4) . . ?
C1 C2 C3 114(4) . . ?
C12 C13 C14 122(4) . . ?
C3 C4 C5 124(5) . . ?
C4 C3 C2 117(5) . . ?
C15 C14 C13 117(4) . . ?
C5 N1 Hg1 119(2) . . ?
C1 N1 Hg1 128(3) . . ?
C1 N1 C5 112(4) . . ?
C10 N2 Hg1 122(3) . . ?
C10 N2 C6 122(4) . . ?
C6 N2 Hg1 115(3) . . ?
N2 C10 C9 126(4) . . ?
C6 C7 C8 113(4) . . ?
N2 C6 C5 120(4) . . ?
N2 C6 C7 122(4) . . ?
C7 C6 C5 118(4) . . ?
C8 C9 C10 111(5) . . ?
C9 C8 C7 127(5) . . ?
C13 C12 C11 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 2.927
_oxdiff_exptl_absorpt_empirical_full_min 0.590
####################################################################### 
# 
# 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_exp1_twin1_hklf4
_database_code_depnum_ccdc_archive 'CCDC 2086287'
loop_
_audit_author_name
_audit_author_address
'Emanuele Priola'
;University of Turin
Italy
;
_audit_update_record             
;
2021-10-26 deposited with the CCDC.	2022-03-07 downloaded from the CCDC.
;
_audit_creation_date             2021-10-19
_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         'C12 H8 Br Hg I N2'
_chemical_formula_sum            'C12 H8 Br Hg I N2'
_chemical_formula_weight         587.60
_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'
Hg Hg -2.3894 9.2266 '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                   7.8750(3)
_cell_length_b                   9.3730(4)
_cell_length_c                   9.8830(4)
_cell_angle_alpha                91.545(3)
_cell_angle_beta                 111.574(4)
_cell_angle_gamma                101.420(3)
_cell_volume                     660.96(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5221
_cell_measurement_temperature    298.00
_cell_measurement_theta_max      27.7100
_cell_measurement_theta_min      3.8770
_shelx_estimated_absorpt_T_max   0.344
_shelx_estimated_absorpt_T_min   0.216
_exptl_absorpt_coefficient_mu    16.979
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81270
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.952
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             524
_exptl_crystal_size_max          0.13
_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  0.1133
_diffrn_reflns_av_unetI/netI     0.0858
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.902
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            13761
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.902
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.388
_diffrn_reflns_theta_min         3.322
_diffrn_ambient_temperature      298.00
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.2890
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.902
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -14.00  85.00   1.00   40.00    --   10.30  37.00  60.00   99
  2  ω    -63.00  38.00   1.00   40.00    --   10.30 -57.00 -30.00  101
  3  ω    -77.00 -32.00   1.00   40.00    --   10.30 179.00  90.00   45
  4  ω    -78.00  98.00   1.00   40.00    --   10.30   0.00   0.00  176
  5  ω    -22.00  86.00   1.00   40.00    --   10.30  77.00  90.00  108
  6  ω    -87.00 -16.00   1.00   40.00    --  -10.37 156.00 122.75   71
  7  ω    -81.00 -11.00   1.00   40.00    --  -10.37 147.00-124.80   70
  8  ω    -89.00 -18.00   1.00   40.00    --  -10.37 159.00  56.86   71
  9  ω    -87.00 -56.00   1.00   40.00    --  -10.37 155.00 -26.28   31
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0868181000
_diffrn_orient_matrix_UB_12      -0.0500298000
_diffrn_orient_matrix_UB_13      -0.0154275000
_diffrn_orient_matrix_UB_21      -0.0277029000
_diffrn_orient_matrix_UB_22      0.0109615000
_diffrn_orient_matrix_UB_23      -0.0751123000
_diffrn_orient_matrix_UB_31      0.0396230000
_diffrn_orient_matrix_UB_32      -0.0583908000
_diffrn_orient_matrix_UB_33      -0.0121857000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1997
_reflns_number_total             3276
_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 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         1.390
_refine_diff_density_min         -1.689
_refine_diff_density_rms         0.196
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.875
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         3276
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0745
_refine_ls_R_factor_gt           0.0411
_refine_ls_restrained_S_all      0.875
_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)+(0.0400P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0852
_refine_ls_wR_factor_ref         0.0924
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Shared sites
{Br1, I2}
{Br2, I1}
3. Uiso/Uaniso restraints and constraints
Uanis(Br1) = Uanis(I2)
Uanis(Br2) = Uanis(I1)
4. Others
 Fixed Sof: I2(0.5) I1(0.5) Br1(0.5) Br2(0.5)
5.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C5(H5), C10(H10), C6(H6), C9(H9), C8(H8)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     heavy
_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
Hg1 Hg 0.51592(4) 0.74214(3) 0.86989(3) 0.05989(14) Uani 1 1 d . . . . .
I2 I 0.24018(8) 0.84769(6) 0.88153(7) 0.05740(18) Uani 0.5 1 d . . P A -1
I1 I 0.79253(9) 0.64771(7) 1.04893(7) 0.06242(19) Uani 0.5 1 d . . P A 1
N2 N 0.3734(8) 0.6079(6) 0.6275(6) 0.0436(13) Uani 1 1 d . . . . .
C12 C 0.4200(9) 0.6757(7) 0.5214(8) 0.0445(16) Uani 1 1 d . . . . .
N1 N 0.6479(8) 0.8630(6) 0.7079(6) 0.0472(14) Uani 1 1 d . . . . .
C11 C 0.5642(9) 0.8067(7) 0.5629(7) 0.0392(15) Uani 1 1 d . . . . .
C1 C 0.2432(10) 0.4846(8) 0.5897(9) 0.0524(19) Uani 1 1 d . . . . .
H1 H 0.212324 0.438579 0.662356 0.063 Uiso 1 1 calc R . . . .
C4 C 0.3309(9) 0.6169(7) 0.3738(8) 0.0439(16) Uani 1 1 d . . . . .
C7 C 0.6199(10) 0.8712(7) 0.4546(8) 0.0464(17) Uani 1 1 d . . . . .
C2 C 0.1506(10) 0.4211(8) 0.4449(10) 0.0541(19) Uani 1 1 d . . . . .
H2 H 0.060059 0.334305 0.422889 0.065 Uiso 1 1 calc R . . . .
C3 C 0.1919(10) 0.4851(8) 0.3365(9) 0.0552(19) Uani 1 1 d . . . . .
H3 H 0.130441 0.443489 0.239742 0.066 Uiso 1 1 calc R . . . .
C5 C 0.3826(11) 0.6878(8) 0.2621(8) 0.0531(19) Uani 1 1 d . . . . .
H5 H 0.318726 0.651894 0.163876 0.064 Uiso 1 1 calc R . . . .
C10 C 0.7852(10) 0.9784(8) 0.7426(9) 0.0545(19) Uani 1 1 d . . . . .
H10 H 0.843870 1.016350 0.840528 0.065 Uiso 1 1 calc R . . . .
C6 C 0.5299(10) 0.8110(7) 0.3044(8) 0.0521(18) Uani 1 1 d . . . . .
H6 H 0.569927 0.854353 0.234573 0.063 Uiso 1 1 calc R . . . .
C9 C 0.8500(11) 1.0487(8) 0.6422(10) 0.058(2) Uani 1 1 d . . . . .
H9 H 0.948971 1.130572 0.674287 0.070 Uiso 1 1 calc R . . . .
C8 C 0.7686(10) 0.9978(8) 0.4981(9) 0.0535(19) Uani 1 1 d . . . . .
H8 H 0.808868 1.044326 0.429778 0.064 Uiso 1 1 calc R . . . .
Br1 Br 0.24018(8) 0.84769(6) 0.88153(7) 0.05740(18) Uani 0.5 1 d . . P A 1
Br2 Br 0.79253(9) 0.64771(7) 1.04893(7) 0.06242(19) Uani 0.5 1 d . . P A -1


_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
Hg1 I2 2.5952(6) . ?
Hg1 I1 2.5832(7) . ?
Hg1 N2 2.425(6) . ?
Hg1 N1 2.405(6) . ?
Hg1 Br1 2.5952(6) . ?
Hg1 Br2 2.5832(7) . ?
N2 C12 1.365(9) . ?
N2 C1 1.323(9) . ?
C12 C11 1.430(9) . ?
C12 C4 1.405(10) . ?
N1 C11 1.376(8) . ?
N1 C10 1.304(9) . ?
C11 C7 1.406(10) . ?
C1 C2 1.396(11) . ?
C4 C3 1.416(10) . ?
C4 C5 1.445(10) . ?
C7 C6 1.431(10) . ?
C7 C8 1.420(10) . ?
C2 C3 1.351(12) . ?
C5 C6 1.393(10) . ?
C10 C9 1.398(11) . ?
C9 C8 1.356(11) . ?

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 Hg1 Br1 0.0 . . ?
I1 Hg1 I2 137.38(2) . . ?
I1 Hg1 Br1 137.38(2) . . ?
N2 Hg1 I2 101.00(12) . . ?
N2 Hg1 I1 114.25(12) . . ?
N2 Hg1 Br1 101.00(12) . . ?
N2 Hg1 Br2 114.25(12) . . ?
N1 Hg1 I2 111.83(12) . . ?
N1 Hg1 I1 102.68(13) . . ?
N1 Hg1 N2 69.64(19) . . ?
N1 Hg1 Br1 111.83(12) . . ?
N1 Hg1 Br2 102.68(13) . . ?
Br2 Hg1 I2 137.38(2) . . ?
Br2 Hg1 I1 0.0 . . ?
Br2 Hg1 Br1 137.38(2) . . ?
C12 N2 Hg1 115.6(4) . . ?
C1 N2 Hg1 125.0(5) . . ?
C1 N2 C12 119.0(6) . . ?
N2 C12 C11 119.0(6) . . ?
N2 C12 C4 120.9(6) . . ?
C4 C12 C11 120.1(6) . . ?
C11 N1 Hg1 116.0(4) . . ?
C10 N1 Hg1 126.8(5) . . ?
C10 N1 C11 117.2(6) . . ?
N1 C11 C12 119.0(6) . . ?
N1 C11 C7 122.2(6) . . ?
C7 C11 C12 118.8(6) . . ?
N2 C1 C2 122.5(7) . . ?
C12 C4 C3 118.8(7) . . ?
C12 C4 C5 120.8(6) . . ?
C3 C4 C5 120.4(7) . . ?
C11 C7 C6 121.1(7) . . ?
C11 C7 C8 118.3(7) . . ?
C8 C7 C6 120.6(7) . . ?
C3 C2 C1 120.4(7) . . ?
C2 C3 C4 118.3(7) . . ?
C6 C5 C4 118.7(6) . . ?
N1 C10 C9 124.3(7) . . ?
C5 C6 C7 120.4(7) . . ?
C8 C9 C10 120.0(7) . . ?
C9 C8 C7 117.9(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 2.318
_oxdiff_exptl_absorpt_empirical_full_min 0.702
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
_oxdiff_twin_reflns_isolated
_oxdiff_twin_reflns_overlapped
_twin_individual_twin_lattice_type
_twin_individual_twin_matrix_11
_twin_individual_twin_matrix_12
_twin_individual_twin_matrix_13
_twin_individual_twin_matrix_21
_twin_individual_twin_matrix_22
_twin_individual_twin_matrix_23
_twin_individual_twin_matrix_31
_twin_individual_twin_matrix_32
_twin_individual_twin_matrix_33
1 0.6989 12337 1885 ref 1.0000 0.0000 0.0000 0.0000 1.0000 0.0000 0.0000 0.0000
1.0000
2 0.3011 12425 1885 nmt -1.0023 -0.0168 -0.5917 0.0009 -0.9998 -0.0027 0.0068
0.0545 1.0023

_twin_special_details            
;
Component 2 rotated by 179.9604° 
around [-0.28 -0.00 0.96] (reciprocal) or [0.00 0.03 1.00] (direct)
;
####################################################################### 
# 
# 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_preex1a
_database_code_depnum_ccdc_archive 'CCDC 2086291'
loop_
_audit_author_name
_audit_author_address
'Emanuele Priola'
;University of Turin
Italy
;
_audit_update_record             
;
2021-05-27 deposited with the CCDC.	2022-03-07 downloaded from the CCDC.
;
_audit_creation_date             2020-06-30
_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         'C10 H8 Br Hg I N2'
_chemical_formula_sum            'C10 H8 Br Hg I N2'
_chemical_formula_weight         563.58
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
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'
Hg Hg -2.3894 9.2266 '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                   8.6535(7)
_cell_length_b                   9.1595(11)
_cell_length_c                   9.3691(11)
_cell_angle_alpha                119.058(12)
_cell_angle_beta                 102.403(8)
_cell_angle_gamma                96.859(8)
_cell_volume                     611.83(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2374
_cell_measurement_temperature    200.00(10)
_cell_measurement_theta_max      36.8140
_cell_measurement_theta_min      3.6850
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    18.335
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.38651
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    3.059
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             500
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0744
_diffrn_reflns_av_unetI/netI     0.0876
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10789
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.506
_diffrn_reflns_theta_min         3.480
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      200.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1990
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -106.00 -45.00   1.00   30.00    --  -29.89 -32.00 -70.00   61
  2  ω    -25.00  11.00   1.00   30.00    --  -29.89  32.00  88.00   36
  3  ω    -42.00  -7.00   1.00   30.00    --  -29.89 -32.00 -70.00   35
  4  ω    -35.00   7.00   1.00   30.00    --   31.14 -32.00 -70.00   42
  5  ω     17.00  43.00   1.00   30.00    --   31.14  68.00 -58.58   26
  6  ω      4.00 105.00   1.00   30.00    --   31.14  70.00  78.34  101
  7  ω     13.00  39.00   1.00   30.00    --   31.14  70.00 141.38   26
  8  ω     69.00  94.00   1.00   30.00    --   31.14  70.00 141.38   25
  9  ω      9.00  97.00   1.00   30.00    --   31.14  68.00 -89.57   88
 10  ω      1.00 105.00   1.00   30.00    --   31.14  70.00  11.53  104
 11  ω      0.00 100.00   1.00   30.00    --   31.14  70.00-170.32  100
 12  ω     32.00  57.00   1.00   30.00    --   31.14  32.00  88.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, AtlasS2, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0346976000
_diffrn_orient_matrix_UB_12      0.0364860000
_diffrn_orient_matrix_UB_13      0.0897131000
_diffrn_orient_matrix_UB_21      0.0061864000
_diffrn_orient_matrix_UB_22      0.0841478000
_diffrn_orient_matrix_UB_23      0.0139886000
_diffrn_orient_matrix_UB_31      -0.0795030000
_diffrn_orient_matrix_UB_32      -0.0038453000
_diffrn_orient_matrix_UB_33      0.0088753000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2587
_reflns_number_total             3725
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.44
_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 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         1.437
_refine_diff_density_min         -1.860
_refine_diff_density_rms         0.274
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         3725
_refine_ls_number_restraints     206
_refine_ls_R_factor_all          0.0827
_refine_ls_R_factor_gt           0.0498
_refine_ls_restrained_S_all      1.015
_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)+(0.0249P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0870
_refine_ls_wR_factor_ref         0.1023
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Rigid bond restraints
 Hg1, N1, N2, Br1B, Br1A, I1B, I1A, C6, C10, C1, C5, C7, H10, C9, H1, C2, C4,
 H7, C8, H9, H2, C3, H4, H8, H3
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
I1A \\sim Br1B \\sim Hg1: within 1.7A with sigma of 0.04 and sigma for terminal
atoms of 0.08
Br1A \\sim Hg1 \\sim N1 \\sim N2 \\sim Br1B \\sim I1B \\sim I1A \\sim C6 \\sim
C10 \\sim C1 \\sim C5 \\sim C7 \\sim H10 \\sim C9 \\sim H1 \\sim C2 \\sim C4
\\sim H7 \\sim C8 \\sim H9 \\sim H2 \\sim C3 \\sim H4 \\sim H8 \\sim H3: within
1.7A with sigma of 0.04 and sigma for terminal atoms of 0.08
Uanis(Br1B) \\sim Ueq, Uanis(I1A) \\sim Ueq, Uanis(Hg1) \\sim Ueq: with sigma
of 0.1 and sigma for terminal atoms of 0.2
4. Others
 Fixed Sof: I1A(0.7) I1B(0.3) Br1A(0.7) Br1B(0.3)
5.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C1(H1), C4(H4), C2(H2), C8(H8), C10(H10), C3(H3), C9(H9)
;
_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
Hg1 Hg 0.20955(4) 0.73926(6) 0.14972(5) 0.03957(13) Uani 1 1 d . U . . .
I1A I 0.4839(6) 0.6987(6) 0.3014(5) 0.0361(5) Uani 0.7 1 d . U P A 1
I1B I -0.0676(4) 0.6575(5) 0.1930(6) 0.0181(7) Uani 0.3 1 d . U P A 2
C7 C 0.3059(11) 1.0042(13) -0.1398(12) 0.0362(19) Uani 1 1 d . U . . .
H7 H 0.303069 1.112741 -0.122462 0.043 Uiso 1 1 calc R U . . .
C1 C 0.1303(11) 1.1225(12) 0.3517(12) 0.0362(19) Uani 1 1 d . U . . .
H1 H 0.109955 1.083107 0.422248 0.043 Uiso 1 1 calc R U . . .
C5 C 0.2112(9) 1.0768(11) 0.1153(10) 0.0279(16) Uani 1 1 d . U . . .
N1 N 0.2658(9) 0.8036(10) -0.0529(10) 0.0325(15) Uani 1 1 d . U . . .
N2 N 0.1787(8) 1.0219(10) 0.2204(10) 0.0320(15) Uani 1 1 d . U . . .
C4 C 0.1945(10) 1.2373(12) 0.1487(12) 0.0359(19) Uani 1 1 d . U . . .
H4 H 0.217812 1.276760 0.079064 0.043 Uiso 1 1 calc R U . . .
C6 C 0.2617(10) 0.9569(11) -0.0316(11) 0.0275(16) Uani 1 1 d . U . . .
C2 C 0.1082(11) 1.2834(14) 0.3897(13) 0.042(2) Uani 1 1 d . U . . .
H2 H 0.071427 1.349997 0.481252 0.051 Uiso 1 1 calc R U . . .
C8 C 0.3534(11) 0.8909(14) -0.2717(13) 0.043(2) Uani 1 1 d . U . . .
H8 H 0.379951 0.920834 -0.346825 0.052 Uiso 1 1 calc R U . . .
C10 C 0.3169(11) 0.6931(12) -0.1793(13) 0.040(2) Uani 1 1 d . U . . .
H10 H 0.322037 0.587376 -0.190496 0.048 Uiso 1 1 calc R U . . .
C3 C 0.1431(12) 1.3391(14) 0.2864(13) 0.043(2) Uani 1 1 d . U . . .
H3 H 0.132045 1.447389 0.308921 0.052 Uiso 1 1 calc R U . . .
C9 C 0.3627(11) 0.7292(13) -0.2953(13) 0.043(2) Uani 1 1 d . U . . .
H9 H 0.397415 0.650696 -0.382950 0.052 Uiso 1 1 calc R U . . .
Br1A Br -0.0636(5) 0.6622(7) 0.2024(7) 0.0700(13) Uani 0.7 1 d . U P A 1
Br1B Br 0.481(3) 0.699(3) 0.270(2) 0.043(2) Uani 0.3 1 d . U P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Hg1 I1A 2.659(5) . ?
Hg1 I1B 3.306(4) 2_565 ?
Hg1 I1B 2.600(3) . ?
Hg1 N1 2.367(7) . ?
Hg1 N2 2.405(8) . ?
Hg1 Br1A 2.602(4) . ?
Hg1 Br1B 2.528(19) . ?
C7 C6 1.384(11) . ?
C7 C8 1.359(14) . ?
C1 N2 1.323(12) . ?
C1 C2 1.386(13) . ?
C5 N2 1.366(10) . ?
C5 C4 1.380(12) . ?
C5 C6 1.482(12) . ?
N1 C6 1.325(11) . ?
N1 C10 1.338(12) . ?
C4 C3 1.382(14) . ?
C2 C3 1.363(13) . ?
C8 C9 1.403(14) . ?
C10 C9 1.397(13) . ?

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
I1A Hg1 I1B 97.93(12) . 2_565 ?
I1B Hg1 I1B 81.86(13) . 2_565 ?
N1 Hg1 I1A 107.0(2) . . ?
N1 Hg1 I1B 130.44(19) . . ?
N1 Hg1 I1B 82.2(2) . 2_565 ?
N1 Hg1 N2 69.2(3) . . ?
N1 Hg1 Br1A 131.8(2) . . ?
N1 Hg1 Br1B 101.3(4) . . ?
N2 Hg1 I1A 121.3(2) . . ?
N2 Hg1 I1B 92.00(18) . . ?
N2 Hg1 I1B 136.26(18) . 2_565 ?
N2 Hg1 Br1A 91.8(2) . . ?
N2 Hg1 Br1B 121.0(5) . . ?
Br1A Hg1 I1A 120.45(14) . . ?
Br1A Hg1 I1B 83.14(12) . 2_565 ?
Br1B Hg1 I1B 96.0(5) . 2_565 ?
Br1B Hg1 I1B 126.8(4) . . ?
Hg1 I1B Hg1 98.14(13) . 2_565 ?
C8 C7 C6 119.5(9) . . ?
N2 C1 C2 123.6(9) . . ?
N2 C5 C4 119.5(8) . . ?
N2 C5 C6 117.1(8) . . ?
C4 C5 C6 123.4(8) . . ?
C6 N1 Hg1 119.7(6) . . ?
C6 N1 C10 119.5(8) . . ?
C10 N1 Hg1 120.4(6) . . ?
C1 N2 Hg1 123.5(6) . . ?
C1 N2 C5 119.6(8) . . ?
C5 N2 Hg1 116.8(6) . . ?
C5 C4 C3 119.5(8) . . ?
C7 C6 C5 121.5(8) . . ?
N1 C6 C7 121.4(9) . . ?
N1 C6 C5 117.1(7) . . ?
C3 C2 C1 116.7(10) . . ?
C7 C8 C9 120.5(9) . . ?
N1 C10 C9 123.0(9) . . ?
C2 C3 C4 121.0(10) . . ?
C10 C9 C8 116.0(9) . . ?

_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 2.029
_oxdiff_exptl_absorpt_empirical_full_min 0.681
####################################################################### 
# 
# 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_preex1a_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2086289'
loop_
_audit_author_name
_audit_author_address
'Emanuele Priola'
;University of Turin
Italy
;
_audit_update_record             
;
2021-05-27 deposited with the CCDC.	2022-03-07 downloaded from the CCDC.
;
_audit_creation_date             2020-06-30
_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         '0.5(C20 H16 Br1.5 Hg2 I2.33 N4)'
_chemical_formula_sum            'C10 H8 Br0.75 Hg I1.15 N2'
_chemical_formula_weight         563.28
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
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'
Hg Hg -2.3894 9.2266 '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           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'

_cell_length_a                   8.6535(7)
_cell_length_b                   9.1595(11)
_cell_length_c                   9.3691(11)
_cell_angle_alpha                119.058(12)
_cell_angle_beta                 102.403(8)
_cell_angle_gamma                96.859(8)
_cell_volume                     611.83(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2374
_cell_measurement_temperature    200.00(10)
_cell_measurement_theta_max      36.8140
_cell_measurement_theta_min      3.6850
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    17.909
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.38651
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    3.058
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             499
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0637
_diffrn_reflns_av_unetI/netI     0.1012
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10789
_diffrn_reflns_point_group_measured_fraction_full 0.820
_diffrn_reflns_point_group_measured_fraction_max 0.783
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.506
_diffrn_reflns_theta_min         3.480
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      200.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1990
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -106.00 -45.00   1.00   30.00    --  -29.89 -32.00 -70.00   61
  2  ω    -25.00  11.00   1.00   30.00    --  -29.89  32.00  88.00   36
  3  ω    -42.00  -7.00   1.00   30.00    --  -29.89 -32.00 -70.00   35
  4  ω    -35.00   7.00   1.00   30.00    --   31.14 -32.00 -70.00   42
  5  ω     17.00  43.00   1.00   30.00    --   31.14  68.00 -58.58   26
  6  ω      4.00 105.00   1.00   30.00    --   31.14  70.00  78.34  101
  7  ω     13.00  39.00   1.00   30.00    --   31.14  70.00 141.38   26
  8  ω     69.00  94.00   1.00   30.00    --   31.14  70.00 141.38   25
  9  ω      9.00  97.00   1.00   30.00    --   31.14  68.00 -89.57   88
 10  ω      1.00 105.00   1.00   30.00    --   31.14  70.00  11.53  104
 11  ω      0.00 100.00   1.00   30.00    --   31.14  70.00-170.32  100
 12  ω     32.00  57.00   1.00   30.00    --   31.14  32.00  88.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, AtlasS2, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0346976000
_diffrn_orient_matrix_UB_12      0.0364860000
_diffrn_orient_matrix_UB_13      0.0897131000
_diffrn_orient_matrix_UB_21      0.0061864000
_diffrn_orient_matrix_UB_22      0.0841478000
_diffrn_orient_matrix_UB_23      0.0139886000
_diffrn_orient_matrix_UB_31      -0.0795030000
_diffrn_orient_matrix_UB_32      -0.0038453000
_diffrn_orient_matrix_UB_33      0.0088753000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.569
_reflns_Friedel_fraction_full    0.642
_reflns_Friedel_fraction_max     0.568
_reflns_number_gt                3871
_reflns_number_total             5843
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.44
_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 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         1.480
_refine_diff_density_min         -2.207
_refine_diff_density_rms         0.320
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.14(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         5843
_refine_ls_number_restraints     201
_refine_ls_R_factor_all          0.0927
_refine_ls_R_factor_gt           0.0550
_refine_ls_restrained_S_all      1.012
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0492P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1210
_refine_ls_wR_factor_ref         0.1465
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Uiso/Uaniso restraints and constraints
Br1a \\sim Hg1: within 1.7A with sigma of 0.004 and sigma for terminal atoms of
0.008
Uanis(N2) \\sim Ueq, Uanis(Hg1) \\sim Ueq, Uanis(I1B) \\sim Ueq, Uanis(I1a)
\\sim Ueq, Uanis(N1) \\sim Ueq, Uanis(Br1a) \\sim Ueq, Uanis(Br1b) \\sim Ueq,
Uanis(C1) \\sim Ueq, Uanis(C5) \\sim Ueq, Uanis(C6) \\sim Ueq, Uanis(C10) \\sim
Ueq, Uanis(C2) \\sim Ueq, Uanis(C4) \\sim Ueq, Uanis(C7) \\sim Ueq, Uanis(C9)
\\sim Ueq, Uanis(C3) \\sim Ueq, Uanis(C8) \\sim Ueq, : with sigma of 0.01 and
sigma for terminal atoms of 0.02
Uanis(Hg2) \\sim Ueq, Uanis(I2B) \\sim Ueq, Uanis(I2a) \\sim Ueq, Uanis(N4)
\\sim Ueq, Uanis(N3) \\sim Ueq, Uanis(Br2) \\sim Ueq, Uanis(C16) \\sim Ueq,
Uanis(C20) \\sim Ueq, Uanis(C15) \\sim Ueq, Uanis(C11) \\sim Ueq, Uanis(C17)
\\sim Ueq, Uanis(C19) \\sim Ueq, Uanis(C14) \\sim Ueq, Uanis(C12) \\sim Ueq,
Uanis(C18) \\sim Ueq, Uanis(C13) \\sim Ueq, : with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(Br1a) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
3. Others
 Sof(I2B)=Sof(I2a)=FVAR(1)
 Fixed Sof: I1B(0.5) I1a(0.5) Br1a(0.5) Br2(0.5) Br1b(0.5)
4.a Aromatic/amide H refined with riding coordinates:
 C1(H9AA), C14(H2), C9(H3), C10(H4), C3(H7), C4(H7AA), C17(H3AA), C8(H4AA),
 C13(H0AA), C7(H), C19(H3BA), C2(H8AA), C20(H2BA), C18(H4BA), C12(H0BA),
 C11(H1BA)
;
_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
Hg0A Hg 0.00172(10) 1.21825(12) 0.23639(12) 0.0411(5) Uani 1 1 d . U . . .
Hg1A Hg 0.42079(10) 0.69677(11) 0.53587(12) 0.0387(5) Uani 1 1 d . U . . .
I0AA I -0.2718(10) 1.2573(16) 0.085(2) 0.0393(16) Uani 0.663(7) 1 d . U P A 1
I1AA I 0.1439(7) 0.6152(9) 0.5786(10) 0.0270(14) Uani 0.5 1 d . U P B 1
I2AA I 0.2772(6) 1.2974(6) 0.1882(7) 0.0359(12) Uani 0.663(7) 1 d . U P A 1
I0A I 0.6983(17) 0.6651(16) 0.6937(15) 0.033(2) Uani 0.5 1 d . U P B 1
N1AA N 0.474(4) 0.760(4) 0.327(4) 0.030(7) Uani 1 1 d . U . . .
N2AA N -0.058(4) 1.153(4) 0.431(4) 0.034(7) Uani 1 1 d . U . . .
C5AA N 0.393(4) 0.982(4) 0.602(4) 0.028(7) Uani 1 1 d . U . . .
C9AA C 0.527(4) 0.656(4) 0.199(4) 0.026(6) Uani 1 1 d . U . . .
H9AA H 0.533432 0.549941 0.186318 0.031 Uiso 1 1 calc R U . . .
C C 0.467(4) 0.919(5) 0.361(4) 0.024(6) Uani 1 1 d . U . . .
C1 C 0.415(4) 1.031(5) 0.498(5) 0.027(7) Uani 1 1 d . U . . .
C2 C 0.021(5) 0.718(6) 0.230(6) 0.042(11) Uani 1 1 d . U . . .
H2 H 0.004473 0.679890 0.302652 0.051 Uiso 1 1 calc R U . . .
C3 C 0.320(5) 1.235(6) 0.777(6) 0.041(10) Uani 1 1 d . U . . .
H3 H 0.275722 1.294842 0.865010 0.049 Uiso 1 1 calc R U . . .
C4 C 0.354(4) 1.081(4) 0.739(5) 0.028(7) Uani 1 1 d . U . . .
H4 H 0.350360 1.044797 0.815102 0.034 Uiso 1 1 calc R U . . .
C5 C -0.058(4) 1.001(4) 0.424(4) 0.024(7) Uani 1 1 d . U . . .
C6 C -0.006(4) 0.883(4) 0.272(4) 0.025(7) Uani 1 1 d . U . . .
C7 C 0.562(4) 0.848(5) 0.121(5) 0.033(7) Uani 1 1 d . U . . .
H7 H 0.593081 0.881442 0.049734 0.039 Uiso 1 1 calc R U . . .
C7AA C 0.515(5) 0.966(5) 0.247(5) 0.030(8) Uani 1 1 d . U . . .
H7AA H 0.512896 1.072641 0.259727 0.036 Uiso 1 1 calc R U . . .
C3AA C -0.096(5) 0.961(6) 0.533(6) 0.040(10) Uani 1 1 d . U . . .
H3AA H -0.086560 0.854577 0.516829 0.048 Uiso 1 1 calc R U . . .
C4AA C 0.356(5) 1.297(6) 0.671(6) 0.036(10) Uani 1 1 d . U . . .
H4AA H 0.344604 1.405117 0.695261 0.044 Uiso 1 1 calc R U . . .
C0AA C 0.065(6) 0.618(7) 0.100(7) 0.052(13) Uani 1 1 d . U . . .
H0AA H 0.072080 0.509036 0.079795 0.062 Uiso 1 1 calc R U . . .
N6AA C 0.410(4) 1.196(5) 0.530(5) 0.029(8) Uani 1 1 d . U . . .
H H 0.440114 1.235917 0.462871 0.035 Uiso 1 1 calc R U . . .
N10 N 0.034(4) 0.936(5) 0.160(5) 0.036(8) Uani 1 1 d . U . . .
C3BA C -0.154(6) 1.232(6) 0.674(6) 0.047(10) Uani 1 1 d . U . . .
H3BA H -0.189478 1.313449 0.758831 0.056 Uiso 1 1 calc R U . . .
C8AA C 0.572(5) 0.688(5) 0.083(5) 0.037(9) Uani 1 1 d . U . . .
H8AA H 0.604398 0.611593 -0.008250 0.044 Uiso 1 1 calc R U . . .
C2BA C -0.108(6) 1.268(6) 0.557(6) 0.051(11) Uani 1 1 d . U . . .
H2BA H -0.112858 1.373888 0.567448 0.062 Uiso 1 1 calc R U . . .
C4BA C -0.147(5) 1.063(6) 0.667(6) 0.046(10) Uani 1 1 d . U . . .
H4BA H -0.173524 1.033615 0.742228 0.056 Uiso 1 1 calc R U . . .
C0BA C 0.102(6) 0.665(6) -0.007(6) 0.043(10) Uani 1 1 d . U . . .
H0BA H 0.130892 0.591744 -0.101957 0.051 Uiso 1 1 calc R U . . .
C1BA C 0.093(5) 0.836(5) 0.034(5) 0.035(9) Uani 1 1 d . U . . .
H1BA H 0.129118 0.878400 -0.028416 0.043 Uiso 1 1 calc R U . . .
Br2 Br 0.690(3) 0.642(3) 0.662(2) 0.027(4) Uani 0.5 1 d . U P B 2
Br4 Br -0.271(3) 1.261(5) 0.109(6) 0.076(9) Uani 0.5 1 d . U P A 2
Br9 Br 0.151(2) 0.621(3) 0.597(3) 0.111(7) Uani 0.5 1 d . U P B 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Hg0A I0AA 2.646(10) . ?
Hg0A I1AA 3.306(7) 1_565 ?
Hg0A I2AA 2.604(5) . ?
Hg0A N2AA 2.31(4) . ?
Hg0A N10 2.39(4) . ?
Hg0A Br4 2.57(3) . ?
Hg1A I1AA 2.595(6) . ?
Hg1A I0A 2.664(14) . ?
Hg1A N1AA 2.41(3) . ?
Hg1A C5AA 2.43(3) . ?
Hg1A Br2 2.60(2) . ?
Hg1A Br9 2.610(19) . ?
N1AA C9AA 1.34(5) . ?
N1AA C 1.34(5) . ?
N2AA C5 1.37(5) . ?
N2AA C2BA 1.35(6) . ?
C5AA C1 1.29(5) . ?
C5AA C4 1.30(5) . ?
C9AA C8AA 1.37(5) . ?
C C1 1.41(5) . ?
C C7AA 1.45(5) . ?
C1 N6AA 1.40(5) . ?
C2 C6 1.42(5) . ?
C2 C0AA 1.30(7) . ?
C3 C4 1.36(5) . ?
C3 C4AA 1.43(6) . ?
C5 C6 1.52(5) . ?
C5 C3AA 1.32(5) . ?
C6 N10 1.44(5) . ?
C7 C7AA 1.34(5) . ?
C7 C8AA 1.34(5) . ?
C3AA C4BA 1.35(6) . ?
C4AA N6AA 1.42(6) . ?
C0AA C0BA 1.35(7) . ?
N10 C1BA 1.35(6) . ?
C3BA C2BA 1.41(7) . ?
C3BA C4BA 1.53(6) . ?
C0BA C1BA 1.43(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
I0AA Hg0A I1AA 98.1(3) . 1_565 ?
I2AA Hg0A I0AA 121.1(3) . . ?
I2AA Hg0A I1AA 82.49(15) . 1_565 ?
N2AA Hg0A I0AA 105.9(8) . . ?
N2AA Hg0A I1AA 82.9(8) . 1_565 ?
N2AA Hg0A I2AA 132.2(8) . . ?
N2AA Hg0A N10 70.6(12) . . ?
N2AA Hg0A Br4 101.8(11) . . ?
N10 Hg0A I0AA 121.0(9) . . ?
N10 Hg0A I1AA 137.1(9) . 1_565 ?
N10 Hg0A I2AA 90.8(9) . . ?
N10 Hg0A Br4 121.5(12) . . ?
Br4 Hg0A I1AA 96.1(9) . 1_565 ?
I1AA Hg1A I0A 122.0(4) . . ?
N1AA Hg1A I1AA 129.7(8) . . ?
N1AA Hg1A I0A 107.5(8) . . ?
N1AA Hg1A C5AA 67.9(11) . . ?
N1AA Hg1A Br2 105.0(9) . . ?
N1AA Hg1A Br9 132.6(9) . . ?
C5AA Hg1A I1AA 93.1(8) . . ?
C5AA Hg1A I0A 119.7(8) . . ?
C5AA Hg1A Br2 123.5(9) . . ?
C5AA Hg1A Br9 93.2(9) . . ?
Br2 Hg1A Br9 121.1(7) . . ?
Hg1A I1AA Hg0A 98.2(2) . 1_545 ?
C9AA N1AA Hg1A 123(2) . . ?
C9AA N1AA C 122(3) . . ?
C N1AA Hg1A 115(2) . . ?
C5 N2AA Hg0A 126(2) . . ?
C2BA N2AA Hg0A 119(3) . . ?
C2BA N2AA C5 115(3) . . ?
C1 C5AA Hg1A 118(3) . . ?
C1 C5AA C4 121(4) . . ?
C4 C5AA Hg1A 120(3) . . ?
N1AA C9AA C8AA 127(3) . . ?
N1AA C C1 122(3) . . ?
N1AA C C7AA 115(3) . . ?
C1 C C7AA 123(3) . . ?
C5AA C1 C 117(3) . . ?
C5AA C1 N6AA 123(4) . . ?
N6AA C1 C 120(3) . . ?
C0AA C2 C6 126(4) . . ?
C4 C3 C4AA 114(4) . . ?
C5AA C4 C3 125(4) . . ?
N2AA C5 C6 109(3) . . ?
C3AA C5 N2AA 126(4) . . ?
C3AA C5 C6 125(4) . . ?
C2 C6 C5 125(4) . . ?
C2 C6 N10 113(3) . . ?
N10 C6 C5 121(3) . . ?
C8AA C7 C7AA 129(4) . . ?
C7 C7AA C 117(3) . . ?
C5 C3AA C4BA 126(4) . . ?
N6AA C4AA C3 121(4) . . ?
C2 C0AA C0BA 122(5) . . ?
C1 N6AA C4AA 115(3) . . ?
C6 N10 Hg0A 113(3) . . ?
C1BA N10 Hg0A 126(3) . . ?
C1BA N10 C6 120(4) . . ?
C2BA C3BA C4BA 122(4) . . ?
C7 C8AA C9AA 110(3) . . ?
N2AA C2BA C3BA 121(4) . . ?
C3AA C4BA C3BA 110(4) . . ?
C0AA C0BA C1BA 116(5) . . ?
N10 C1BA C0BA 122(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 2.029
_oxdiff_exptl_absorpt_empirical_full_min 0.681
####################################################################### 
# 
# 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_preex1_CCDC4
_database_code_depnum_ccdc_archive 'CCDC 2086278'
loop_
_audit_author_name
_audit_author_address
'Emanuele Priola'
;University of Turin
Italy
;
_audit_update_record             
;
2021-10-26 deposited with the CCDC.	2022-03-07 downloaded from the CCDC.
;
_audit_creation_date             2021-10-19
_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         'C8 H6 Br2 Hg2 I2 N4'
_chemical_formula_sum            'C8 H6 Br2 Hg2 I2 N4'
_chemical_formula_weight         972.97
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
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'
Hg Hg -2.3894 9.2266 '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                   7.4986(9)
_cell_length_b                   13.7515(12)
_cell_length_c                   8.5348(8)
_cell_angle_alpha                90
_cell_angle_beta                 93.782(10)
_cell_angle_gamma                90
_cell_volume                     878.17(15)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1993
_cell_measurement_temperature    298.00
_cell_measurement_theta_max      25.7800
_cell_measurement_theta_min      3.7310
_shelx_estimated_absorpt_T_max   0.362
_shelx_estimated_absorpt_T_min   0.166
_exptl_absorpt_coefficient_mu    25.515
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.12114
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    3.680
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             836
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0520
_diffrn_reflns_av_unetI/netI     0.0522
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            5983
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_min         3.805
_diffrn_ambient_temperature      298.00
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.2890
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -55.00  36.00   1.00   15.00    --   10.45 -57.00 -90.00   91
  2  ω    -10.00  83.00   1.00   15.00    --   10.45  57.00  60.00   93
  3  ω    -71.00  15.00   1.00   15.00    --  -10.53 -57.00 120.00   86
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0713545000
_diffrn_orient_matrix_UB_12      0.0060634000
_diffrn_orient_matrix_UB_13      0.0579690000
_diffrn_orient_matrix_UB_21      0.0582311000
_diffrn_orient_matrix_UB_22      -0.0245850000
_diffrn_orient_matrix_UB_23      -0.0489022000
_diffrn_orient_matrix_UB_31      0.0222289000
_diffrn_orient_matrix_UB_32      0.0449549000
_diffrn_orient_matrix_UB_33      -0.0344787000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1204
_reflns_number_total             1795
_reflns_odcompleteness_completeness 99.68
_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 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         2.673
_refine_diff_density_min         -1.637
_refine_diff_density_rms         0.322
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     82
_refine_ls_number_reflns         1795
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0932
_refine_ls_R_factor_gt           0.0599
_refine_ls_restrained_S_all      1.066
_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)+(0.1101P)²+2.9938P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1667
_refine_ls_wR_factor_ref         0.2066
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Shared sites
{Br1, I2}
{I1, Br2}
3. Uiso/Uaniso restraints and constraints
Uanis(Br1) = Uanis(I2)
Uanis(I1) = Uanis(Br2)
4. Others
 Fixed Sof: Br1(0.5) I1(0.5) I2(0.5) Br2(0.5)
5.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     heavy
_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
Hg1 Hg 0.43146(11) 0.68963(5) 0.25954(9) 0.0747(4) Uani 1 1 d . . . . .
Br1 Br 0.6599(2) 0.82464(11) 0.35079(17) 0.0717(5) Uani 0.5 1 d . . P A 1
I1 I 0.1701(3) 0.63175(13) 0.0779(2) 0.0882(6) Uani 0.5 1 d . . P A 1
N1 N 0.628(2) 0.5458(10) 0.3405(15) 0.058(3) Uani 1 1 d . . . . .
C1 C 0.779(3) 0.5253(16) 0.277(2) 0.080(5) Uani 1 1 d . . . . .
H1 H 0.809063 0.563313 0.192255 0.096 Uiso 1 1 calc R . . . .
N2 N 0.685(2) 0.4139(9) 0.5142(16) 0.063(4) Uani 1 1 d . . . . .
C4 C 0.585(3) 0.4891(12) 0.4634(17) 0.063(4) Uani 1 1 d . . . . .
C3 C 0.835(3) 0.3969(17) 0.444(2) 0.075(5) Uani 1 1 d . . . . .
H3 H 0.905558 0.344227 0.477554 0.090 Uiso 1 1 calc R . . . .
C2 C 0.890(3) 0.4556(16) 0.323(2) 0.075(5) Uani 1 1 d . . . . .
H2 H 0.998182 0.445850 0.277329 0.090 Uiso 1 1 calc R . . . .
I2 I 0.6599(2) 0.82464(11) 0.35079(17) 0.0717(5) Uani 0.5 1 d . . P A -1
Br2 Br 0.1701(3) 0.63175(13) 0.0779(2) 0.0882(6) Uani 0.5 1 d . . P A -1


_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
Hg1 Br1 2.6100(15) . ?
Hg1 I1 2.5449(18) . ?
Hg1 N1 2.537(13) . ?
Hg1 N2 2.595(14) 3_666 ?
Hg1 I2 2.6100(15) . ?
Hg1 Br2 2.5449(18) . ?
N1 C1 1.32(2) . ?
N1 C4 1.36(2) . ?
C1 C2 1.31(3) . ?
N2 C4 1.33(2) . ?
N2 C3 1.33(3) . ?
C4 C4 1.49(4) 3_666 ?
C3 C2 1.40(3) . ?

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 Hg1 Br1 150.24(6) . . ?
I1 Hg1 N2 90.0(3) . 3_666 ?
I1 Hg1 I2 150.24(6) . . ?
N1 Hg1 Br1 96.6(3) . . ?
N1 Hg1 I1 109.5(3) . . ?
N1 Hg1 N2 65.6(5) . 3_666 ?
N1 Hg1 I2 96.6(3) . . ?
N1 Hg1 Br2 109.5(3) . . ?
N2 Hg1 Br1 114.4(3) 3_666 . ?
N2 Hg1 I2 114.4(3) 3_666 . ?
I2 Hg1 Br1 0.0 . . ?
Br2 Hg1 Br1 150.24(6) . . ?
Br2 Hg1 I1 0.0 . . ?
Br2 Hg1 N2 90.0(3) . 3_666 ?
Br2 Hg1 I2 150.24(6) . . ?
C1 N1 Hg1 123.7(13) . . ?
C1 N1 C4 116.8(16) . . ?
C4 N1 Hg1 119.4(12) . . ?
C2 C1 N1 125(2) . . ?
C4 N2 Hg1 117.4(12) . 3_666 ?
C3 N2 Hg1 124.9(13) . 3_666 ?
C3 N2 C4 117.7(16) . . ?
N1 C4 C4 117.6(19) . 3_666 ?
N2 C4 N1 122.5(17) . . ?
N2 C4 C4 119.9(17) . 3_666 ?
N2 C3 C2 122(2) . . ?
C1 C2 C3 115(2) . . ?


_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 4.086
_oxdiff_exptl_absorpt_empirical_full_min 0.408
####################################################################### 
# 
# 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_exp(rid5)
_database_code_depnum_ccdc_archive 'CCDC 2086282'
loop_
_audit_author_name
_audit_author_address
'Emanuele Priola'
;University of Turin
Italy
;
_audit_update_record             
;
2021-10-26 deposited with the CCDC.	2022-03-07 downloaded from the CCDC.
;
_audit_creation_date             2021-10-15
_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         'C13 H9 Br Hg I N3'
_chemical_formula_sum            'C13 H9 Br Hg I N3'
_chemical_formula_weight         614.63
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
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'
Hg Hg -2.3894 9.2266 '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                   7.88287(18)
_cell_length_b                   8.4128(2)
_cell_length_c                   12.8356(4)
_cell_angle_alpha                76.521(2)
_cell_angle_beta                 88.160(2)
_cell_angle_gamma                64.590(2)
_cell_volume                     745.46(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    12603
_cell_measurement_temperature    298.00
_cell_measurement_theta_max      26.8360
_cell_measurement_theta_min      3.5280
_shelx_estimated_absorpt_T_max   0.288
_shelx_estimated_absorpt_T_min   0.211
_exptl_absorpt_coefficient_mu    15.063
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.17349
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    2.738
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.15
_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  0.0583
_diffrn_reflns_av_unetI/netI     0.0254
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            29565
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         3.194
_diffrn_ambient_temperature      298.00
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.2890
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -63.00  38.00   1.00    7.50    --   10.30 -57.00 150.00  101
  2  ω    -39.00  63.00   1.00    7.50    --  -10.37  57.00-150.00  102
  3  ω    -39.00  63.00   1.00    7.50    --  -10.37  57.00 -30.00  102
  4  ω    -84.00  18.00   1.00    7.50    --  -10.37 -57.00 -90.00  102
  5  ω    -39.00  63.00   1.00    7.50    --  -10.37  57.00  60.00  102
  6  ω    -85.00  14.00   1.00    7.50    --  -10.37 -37.00 120.00   99
  7  ω    -84.00  20.00   1.00    7.50    --  -10.37 -68.00  79.42  104
  8  ω    -39.00  63.00   1.00    7.50    --  -10.37  57.00 150.00  102
  9  ω    -39.00  63.00   1.00    7.50    --  -10.37  57.00  30.00  102
 10  ω    -39.00  63.00   1.00    7.50    --  -10.37  57.00 -60.00  102
 11  ω    -99.00  78.00   1.00    7.50    --  -10.37   0.00-180.00  177
 12  ω    -99.00  78.00   1.00    7.50    --  -10.37   0.00-150.00  177
 13  ω    -39.00  63.00   1.00    7.50    --  -10.37  57.00 -90.00  102
 14  ω    -99.00 -36.00   1.00    7.50    --  -10.37   0.00-120.00   63
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0289122000
_diffrn_orient_matrix_UB_12      -0.0478274000
_diffrn_orient_matrix_UB_13      0.0444852000
_diffrn_orient_matrix_UB_21      0.0119726000
_diffrn_orient_matrix_UB_22      0.0522628000
_diffrn_orient_matrix_UB_23      0.0327395000
_diffrn_orient_matrix_UB_31      -0.0948885000
_diffrn_orient_matrix_UB_32      0.0651169000
_diffrn_orient_matrix_UB_33      -0.0140628000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2556
_reflns_number_total             3028
_reflns_odcompleteness_completeness 99.80
_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 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.867
_refine_diff_density_min         -0.994
_refine_diff_density_rms         0.122
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         3028
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0421
_refine_ls_R_factor_gt           0.0322
_refine_ls_restrained_S_all      1.041
_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)+(0.0384P)²+1.3739P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0756
_refine_ls_wR_factor_ref         0.0807
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Shared sites
{Br1, I2}
{Br2, I1}
3. Uiso/Uaniso restraints and constraints
Uanis(Br1) = Uanis(I2)
Uanis(Br2) = Uanis(I1)
4. Others
 Fixed Sof: I1(0.5) I2(0.5) Br1(0.5) Br2(0.5)
5.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C8(H8), C3(H3), C7(H7), C2(H2), C12(H12), C4(H4), C10(H10), C11(H11)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     heavy
_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
Hg1 Hg 0.68741(4) 0.86603(3) 0.70157(2) 0.05918(12) Uani 1 1 d . . . . .
I1 I 0.39210(8) 0.85358(8) 0.62687(5) 0.06232(16) Uani 0.5 1 d . . P A 1
I2 I 0.80372(9) 1.09589(8) 0.73188(5) 0.07076(18) Uani 0.5 1 d . . P A -1
N2 N 0.8262(8) 0.5899(7) 0.8362(5) 0.0533(13) Uani 1 1 d . . . . .
N1 N 0.9717(7) 0.6418(7) 0.6460(5) 0.0538(13) Uani 1 1 d . . . . .
N3 N 0.6106(8) 0.7362(9) 0.9458(5) 0.0625(15) Uani 1 1 d . . . . .
C6 C 0.9634(9) 0.4449(9) 0.8146(6) 0.0547(16) Uani 1 1 d . . . . .
C5 C 1.0470(9) 0.4725(9) 0.7095(5) 0.0526(15) Uani 1 1 d . . . . .
C9 C 0.8110(10) 0.4121(10) 1.0107(6) 0.0601(17) Uani 1 1 d . . . . .
C1 C 1.0496(10) 0.6759(9) 0.5559(6) 0.0620(18) Uani 1 1 d . . . . .
H1 H 0.996872 0.793006 0.512143 0.074 Uiso 1 1 calc R . . . .
C13 C 0.7469(10) 0.5787(10) 0.9318(6) 0.0577(17) Uani 1 1 d . . . . .
C8 C 0.9549(11) 0.2604(10) 0.9865(6) 0.068(2) Uani 1 1 d . . . . .
H8 H 0.997782 0.148842 1.036151 0.081 Uiso 1 1 calc R . . . .
C3 C 1.2811(10) 0.3734(10) 0.5868(6) 0.069(2) Uani 1 1 d . . . . .
H3 H 1.385466 0.282043 0.567251 0.083 Uiso 1 1 calc R . . . .
C7 C 1.0347(11) 0.2737(9) 0.8894(6) 0.0652(19) Uani 1 1 d . . . . .
H7 H 1.132696 0.172982 0.873612 0.078 Uiso 1 1 calc R . . . .
C2 C 1.2065(11) 0.5449(10) 0.5237(7) 0.0671(19) Uani 1 1 d . . . . .
H2 H 1.259187 0.573980 0.460429 0.081 Uiso 1 1 calc R . . . .
C12 C 0.5332(11) 0.7289(12) 1.0368(7) 0.072(2) Uani 1 1 d . . . . .
H12 H 0.436787 0.835745 1.047045 0.086 Uiso 1 1 calc R . . . .
C4 C 1.2002(11) 0.3376(10) 0.6795(6) 0.069(2) Uani 1 1 d . . . . .
H4 H 1.249315 0.220225 0.722964 0.083 Uiso 1 1 calc R . . . .
C10 C 0.7226(12) 0.4139(13) 1.1066(6) 0.073(2) Uani 1 1 d . . . . .
H10 H 0.758207 0.307545 1.160410 0.088 Uiso 1 1 calc R . . . .
C11 C 0.5844(13) 0.5715(14) 1.1211(7) 0.079(2) Uani 1 1 d . . . . .
H11 H 0.525076 0.575577 1.184866 0.095 Uiso 1 1 calc R . . . .
Br1 Br 0.80372(9) 1.09589(8) 0.73188(5) 0.07076(18) Uani 0.5 1 d . . P A 1
Br2 Br 0.39210(8) 0.85358(8) 0.62687(5) 0.06232(16) Uani 0.5 1 d . . P A -1


_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
Hg1 I1 2.5978(6) . ?
Hg1 I2 2.5743(6) . ?
Hg1 N2 2.377(5) . ?
Hg1 N1 2.447(5) . ?
Hg1 Br1 2.5743(6) . ?
Hg1 Br2 2.5978(6) . ?
N2 C6 1.319(8) . ?
N2 C13 1.361(9) . ?
N1 C5 1.345(8) . ?
N1 C1 1.322(9) . ?
N3 C13 1.349(9) . ?
N3 C12 1.301(10) . ?
C6 C5 1.494(10) . ?
C6 C7 1.417(10) . ?
C5 C4 1.376(10) . ?
C9 C13 1.417(10) . ?
C9 C8 1.389(11) . ?
C9 C10 1.396(11) . ?
C1 C2 1.387(10) . ?
C8 C7 1.380(11) . ?
C3 C2 1.357(11) . ?
C3 C4 1.365(11) . ?
C12 C11 1.410(12) . ?
C10 C11 1.357(13) . ?

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 Hg1 I1 140.79(2) . . ?
I2 Hg1 Br2 140.79(2) . . ?
N2 Hg1 I1 102.87(12) . . ?
N2 Hg1 I2 110.98(12) . . ?
N2 Hg1 N1 67.68(19) . . ?
N2 Hg1 Br1 110.98(12) . . ?
N2 Hg1 Br2 102.87(12) . . ?
N1 Hg1 I1 109.57(13) . . ?
N1 Hg1 I2 101.34(12) . . ?
N1 Hg1 Br1 101.34(12) . . ?
N1 Hg1 Br2 109.57(13) . . ?
Br1 Hg1 I1 140.79(2) . . ?
Br1 Hg1 I2 0.0 . . ?
Br1 Hg1 Br2 140.79(2) . . ?
Br2 Hg1 I1 0.0 . . ?
C6 N2 Hg1 120.6(5) . . ?
C6 N2 C13 120.6(6) . . ?
C13 N2 Hg1 118.4(5) . . ?
C5 N1 Hg1 117.3(4) . . ?
C1 N1 Hg1 123.9(4) . . ?
C1 N1 C5 118.8(6) . . ?
C12 N3 C13 116.4(7) . . ?
N2 C6 C5 116.6(6) . . ?
N2 C6 C7 121.7(7) . . ?
C7 C6 C5 121.6(6) . . ?
N1 C5 C6 116.5(6) . . ?
N1 C5 C4 120.1(7) . . ?
C4 C5 C6 123.2(6) . . ?
C8 C9 C13 117.9(7) . . ?
C8 C9 C10 125.2(8) . . ?
C10 C9 C13 116.9(7) . . ?
N1 C1 C2 123.0(7) . . ?
N2 C13 C9 120.9(7) . . ?
N3 C13 N2 115.3(6) . . ?
N3 C13 C9 123.8(7) . . ?
C7 C8 C9 120.7(7) . . ?
C2 C3 C4 118.8(7) . . ?
C8 C7 C6 118.3(7) . . ?
C3 C2 C1 118.3(7) . . ?
N3 C12 C11 125.0(8) . . ?
C3 C4 C5 121.0(7) . . ?
C11 C10 C9 119.7(8) . . ?
C10 C11 C12 118.2(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 3.741
_oxdiff_exptl_absorpt_empirical_full_min 0.605
####################################################################### 
# 
# 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_preex1_CCDC5
_database_code_depnum_ccdc_archive 'CCDC 2086280'
loop_
_audit_author_name
_audit_author_address
'Emanuele Priola'
;University of Turin
Italy
;
_audit_update_record             
;
2021-10-26 deposited with the CCDC.	2022-03-07 downloaded from the CCDC.
;
_audit_creation_date             2021-10-18
_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         'C12 H12 Br Hg I N2'
_chemical_formula_sum            'C12 H12 Br Hg I N2'
_chemical_formula_weight         591.64
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
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'
Hg Hg -2.3894 9.2266 '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           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   14.9218(16)
_cell_length_b                   13.996(2)
_cell_length_c                   15.1066(17)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3155.0(7)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4443
_cell_measurement_temperature    297.00
_cell_measurement_theta_max      23.7660
_cell_measurement_theta_min      3.3610
_shelx_estimated_absorpt_T_max   0.396
_shelx_estimated_absorpt_T_min   0.259
_exptl_absorpt_coefficient_mu    14.229
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84555
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.491
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             2128
_exptl_crystal_size_max          0.13
_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  0.0885
_diffrn_reflns_av_unetI/netI     0.0529
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            25849
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         3.355
_diffrn_ambient_temperature      297.00
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.2890
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -64.00  32.00   1.00   10.00    --   10.45 -37.00  30.00   96
  2  ω     -9.00  84.00   1.00   10.00    --   10.45  57.00-180.00   93
  3  ω    -38.00 -12.00   1.00   10.00    --  -10.53 -57.00-180.00   26
  4  ω    -82.00  -4.00   1.00   10.00    --  -10.53 -57.00 -90.00   78
  5  ω    -81.00 -39.00   1.00   10.00    --  -10.53 -37.00 -30.00   42
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0446597000
_diffrn_orient_matrix_UB_12      -0.0029128000
_diffrn_orient_matrix_UB_13      0.0158787000
_diffrn_orient_matrix_UB_21      -0.0062737000
_diffrn_orient_matrix_UB_22      -0.0429434000
_diffrn_orient_matrix_UB_23      -0.0241347000
_diffrn_orient_matrix_UB_31      0.0150750000
_diffrn_orient_matrix_UB_32      -0.0266687000
_diffrn_orient_matrix_UB_33      0.0370451000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1913
_reflns_number_total             3224
_reflns_odcompleteness_completeness 99.56
_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 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         1.904
_refine_diff_density_min         -1.705
_refine_diff_density_rms         0.225
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         3224
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1065
_refine_ls_R_factor_gt           0.0565
_refine_ls_restrained_S_all      1.038
_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)+(0.0819P)²+23.8373P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1501
_refine_ls_wR_factor_ref         0.1822
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Shared sites
{I1, Br2}
{Br1, I2}
3. Uiso/Uaniso restraints and constraints
Uanis(I1) = Uanis(Br2)
Uanis(Br1) = Uanis(I2)
4. Others
 Fixed Sof: Br1(0.5) I1(0.5) I2(0.5) Br2(0.5)
5.a Aromatic/amide H refined with riding coordinates:
 C1AA(H1AA), C1(H1), C7(H7), C4(H4), C8(H8), C3(H3)
5.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     heavy
_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
Hg1 Hg 0.78760(4) 0.10127(5) 0.61957(4) 0.0631(3) Uani 1 1 d . . . . .
Br1 Br 0.73959(9) 0.21660(10) 0.75040(8) 0.0737(4) Uani 0.5 1 d . . P A 1
I1 I 0.68801(9) 0.00016(11) 0.50883(10) 0.0824(5) Uani 0.5 1 d . . P A 1
N1 N 0.9178(7) 0.0204(8) 0.6705(7) 0.052(3) Uani 1 1 d . . . . .
N2 N 0.9150(7) 0.1552(8) 0.5382(6) 0.049(3) Uani 1 1 d . . . . .
C6 C 0.9957(9) 0.0428(10) 0.6319(8) 0.049(3) Uani 1 1 d . . . . .
C5 C 0.9945(9) 0.1146(9) 0.5576(8) 0.048(3) Uani 1 1 d . . . . .
C1AA C 0.9172(11) -0.0417(10) 0.7375(9) 0.059(4) Uani 1 1 d . . . . .
H1AA H 0.862054 -0.056717 0.762496 0.071 Uiso 1 1 calc R . . . .
C1 C 0.9129(10) 0.2229(10) 0.4749(8) 0.057(3) Uani 1 1 d . . . . .
H1 H 0.857789 0.249977 0.460868 0.068 Uiso 1 1 calc R . . . .
C9 C 0.9910(11) -0.0846(11) 0.7720(9) 0.061(4) Uani 1 1 d . . . . .
C7 C 1.0740(10) -0.0014(11) 0.6616(10) 0.062(4) Uani 1 1 d . . . . .
H7 H 1.128230 0.011516 0.633766 0.075 Uiso 1 1 calc R . . . .
C4 C 1.0702(10) 0.1408(11) 0.5141(9) 0.064(4) Uani 1 1 d . . . . .
H4 H 1.124426 0.111374 0.527274 0.076 Uiso 1 1 calc R . . . .
C11 C 0.9794(12) 0.3308(14) 0.3612(11) 0.083(5) Uani 1 1 d . . . . .
H11A H 0.924602 0.322369 0.328826 0.124 Uiso 1 1 calc GR . . . .
H11B H 1.029284 0.327113 0.321210 0.124 Uiso 1 1 calc GR . . . .
H11C H 0.979068 0.392175 0.389584 0.124 Uiso 1 1 calc GR . . . .
C8 C 1.0713(12) -0.0634(12) 0.7309(10) 0.072(4) Uani 1 1 d . . . . .
H8 H 1.123971 -0.091656 0.750805 0.086 Uiso 1 1 calc R . . . .
C2 C 0.9875(9) 0.2544(10) 0.4294(8) 0.053(3) Uani 1 1 d . . . . .
C3 C 1.0664(11) 0.2115(11) 0.4500(10) 0.065(4) Uani 1 1 d . . . . .
H3 H 1.118491 0.229689 0.420719 0.078 Uiso 1 1 calc R . . . .
C10 C 0.9865(14) -0.1542(14) 0.8464(12) 0.098(6) Uani 1 1 d . . . . .
H10A H 1.019416 -0.129679 0.896020 0.147 Uiso 1 1 calc GR . . . .
H10B H 1.012042 -0.213880 0.827976 0.147 Uiso 1 1 calc GR . . . .
H10C H 0.925062 -0.163766 0.863073 0.147 Uiso 1 1 calc GR . . . .
I2 I 0.73959(9) 0.21660(10) 0.75040(8) 0.0737(4) Uani 0.5 1 d . . P A -1
Br2 Br 0.68801(9) 0.00016(11) 0.50883(10) 0.0824(5) Uani 0.5 1 d . . P A -1


_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
Hg1 Br1 2.6504(14) . ?
Hg1 I1 2.6476(14) . ?
Hg1 N1 2.377(11) . ?
Hg1 N2 2.387(10) . ?
Hg1 I2 2.6504(14) . ?
Hg1 Br2 2.6476(14) . ?
N1 C6 1.338(16) . ?
N1 C1AA 1.333(16) . ?
N2 C5 1.348(16) . ?
N2 C1 1.346(16) . ?
C6 C5 1.506(19) . ?
C6 C7 1.396(19) . ?
C5 C4 1.357(19) . ?
C1AA C9 1.36(2) . ?
C1 C2 1.381(18) . ?
C9 C8 1.38(2) . ?
C9 C10 1.49(2) . ?
C7 C8 1.36(2) . ?
C4 C3 1.39(2) . ?
C11 C2 1.49(2) . ?
C2 C3 1.36(2) . ?

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
Br1 Hg1 I2 0.0 . . ?
I1 Hg1 Br1 130.17(5) . . ?
I1 Hg1 I2 130.17(5) . . ?
N1 Hg1 Br1 105.6(3) . . ?
N1 Hg1 I1 114.1(3) . . ?
N1 Hg1 N2 70.5(4) . . ?
N1 Hg1 I2 105.6(3) . . ?
N1 Hg1 Br2 114.1(3) . . ?
N2 Hg1 Br1 114.0(3) . . ?
N2 Hg1 I1 106.9(2) . . ?
N2 Hg1 I2 114.0(3) . . ?
N2 Hg1 Br2 106.9(2) . . ?
Br2 Hg1 Br1 130.17(5) . . ?
Br2 Hg1 I1 0.0 . . ?
Br2 Hg1 I2 130.17(5) . . ?
C6 N1 Hg1 117.2(8) . . ?
C1AA N1 Hg1 123.4(10) . . ?
C1AA N1 C6 119.3(12) . . ?
C5 N2 Hg1 117.1(8) . . ?
C1 N2 Hg1 124.7(9) . . ?
C1 N2 C5 118.2(11) . . ?
N1 C6 C5 118.2(11) . . ?
N1 C6 C7 118.8(13) . . ?
C7 C6 C5 123.0(12) . . ?
N2 C5 C6 117.0(11) . . ?
N2 C5 C4 120.8(12) . . ?
C4 C5 C6 122.1(13) . . ?
N1 C1AA C9 125.0(15) . . ?
N2 C1 C2 124.0(13) . . ?
C1AA C9 C8 115.8(14) . . ?
C1AA C9 C10 122.8(16) . . ?
C8 C9 C10 121.2(15) . . ?
C8 C7 C6 120.4(14) . . ?
C5 C4 C3 119.9(14) . . ?
C7 C8 C9 120.5(14) . . ?
C1 C2 C11 120.5(14) . . ?
C3 C2 C1 116.3(13) . . ?
C3 C2 C11 123.2(13) . . ?
C2 C3 C4 120.8(13) . . ?


_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 1.189
_oxdiff_exptl_absorpt_empirical_full_min 0.837
