# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2020

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2022319'
loop_
_audit_author_name
_audit_author_address
'Damir Safin'
;University of Tyumen
Russia
;
# end Validation Reply Form

_audit_update_record             
;
2020-11-09 deposited with the CCDC.	2020-11-18 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT342_shelx               
;
PROBLEM: Low Bond Precision on C-C Bonds ............... 0.0214 Ang. 
RESPONSE: This was caused by the quality of the crystal and by measurements
at 300 K. Crystals were formed directly during the synthesis, while
recrystallization did not produce any crystals. Measurements at low temperatures
yielded the same structure and no polymorph transformation was fixed but
extensive crystal cracking.
;
_vrf_PLAT971_shelx               
;
PROBLEM: Check Calcd Resid. Dens. 1.18A From Hg1 2.84 eA-3 
RESPONSE: see RESPONSE described above
;
_vrf_PLAT972_shelx               
;
PROBLEM: Check Calcd Resid. Dens. 1.23A From Hg1 -3.10 eA-3 
RESPONSE: see RESPONSE described above
;
_vrf_PLAT973_shelx               
;
PROBLEM: Check Calcd Positive Resid. Density on Hg1 1.88 eA-3 
RESPONSE: see RESPONSE described above
;
_publcif_datablock.id            {e2845047-39b7-49d2-85db-697ca874eb51}

# publcif _publ_body_element loop end

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H10 Hg2 N16'
_chemical_formula_sum            'C12 H10 Hg2 N16'
_chemical_formula_weight         779.54

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'
N N 0.0061 0.0033 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.1276(16)
_cell_length_b                   7.8720(15)
_cell_length_c                   9.358(2)
_cell_angle_alpha                89.837(7)
_cell_angle_beta                 82.547(7)
_cell_angle_gamma                74.782(7)
_cell_volume                     502.08(19)
_cell_formula_units_Z            1
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    1749
_cell_measurement_theta_min      2.99
_cell_measurement_theta_max      24.98

_exptl_crystal_description       needle
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.578
_exptl_crystal_F_000             354
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    15.308
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2465
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'

_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      300(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5036
_diffrn_reflns_av_unetI/netI     0.0938
_diffrn_reflns_av_R_equivalents  0.0818
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.989
_diffrn_reflns_theta_max         25.694
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             1871
_reflns_number_gt                1545
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1074P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1871
_refine_ls_number_parameters     136
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0723
_refine_ls_R_factor_gt           0.0596
_refine_ls_wR_factor_ref         0.1651
_refine_ls_wR_factor_gt          0.1556
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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 0.28123(7) 0.40120(7) 0.44962(5) 0.0435(3) Uani 1 1 d . . . . .
N2 N 0.263(2) 0.2266(16) 0.2263(11) 0.047(3) Uani 1 1 d . . . . .
C3 C 0.3205(17) 0.0483(19) 0.2227(12) 0.036(3) Uani 1 1 d . . . . .
C4 C 0.302(2) -0.055(2) 0.1085(15) 0.042(3) Uani 1 1 d . . . . .
H4 H 0.340820 -0.177040 0.109217 0.050 Uiso 1 1 calc R U . . .
C5 C 0.222(2) 0.034(2) -0.0076(14) 0.051(4) Uani 1 1 d . . . . .
H5 H 0.208081 -0.029294 -0.087309 0.061 Uiso 1 1 calc R U . . .
C6 C 0.166(3) 0.208(3) -0.0057(18) 0.052(4) Uani 1 1 d . . . . .
H6 H 0.117158 0.266075 -0.085157 0.063 Uiso 1 1 calc R U . . .
C7 C 0.179(2) 0.304(2) 0.1162(17) 0.053(5) Uani 1 1 d . . . . .
H7 H 0.128390 0.426138 0.119974 0.064 Uiso 1 1 calc R U . . .
C8 C 0.420(2) -0.0376(19) 0.3468(14) 0.041(3) Uani 1 1 d . . . . .
H8 H 0.454045 -0.159867 0.350155 0.050 Uiso 1 1 calc R U . . .
N9 N 0.4598(17) 0.0495(15) 0.4463(11) 0.036(2) Uani 1 1 d . . . . .
N10 N 0.489(2) 0.5272(19) 0.3378(15) 0.058(4) Uani 1 1 d . . . . .
N11 N 0.576(2) 0.4531(19) 0.2249(16) 0.051(3) Uani 1 1 d . . . . .
N12 N 0.674(3) 0.396(3) 0.1188(19) 0.093(7) Uani 1 1 d . . . . .
N13 N 0.062(2) 0.359(2) 0.6074(15) 0.063(4) Uani 1 1 d . . . . .
N14 N 0.0604(17) 0.204(2) 0.6265(12) 0.046(3) Uani 1 1 d . . . . .
N15 N 0.059(3) 0.061(3) 0.6558(19) 0.091(6) Uani 1 1 d . . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Hg1 0.0460(4) 0.0391(5) 0.0422(3) -0.0053(2) 0.0026(2) -0.0098(3)
N2 0.066(8) 0.037(8) 0.039(5) -0.007(5) -0.006(5) -0.015(6)
C3 0.024(6) 0.053(10) 0.032(5) -0.005(5) 0.002(4) -0.013(6)
C4 0.030(6) 0.044(10) 0.050(7) -0.003(6) 0.004(5) -0.013(6)
C5 0.044(8) 0.070(13) 0.038(6) -0.016(7) -0.003(6) -0.015(8)
C6 0.053(9) 0.057(13) 0.048(7) 0.005(7) -0.016(7) -0.012(8)
C7 0.062(10) 0.032(10) 0.058(8) 0.006(7) -0.027(8) 0.014(7)
C8 0.047(8) 0.023(8) 0.050(7) 0.000(5) 0.003(6) -0.007(6)
N9 0.044(6) 0.023(7) 0.042(5) 0.003(4) -0.006(5) -0.014(5)
N10 0.070(9) 0.042(9) 0.068(8) -0.020(6) 0.022(7) -0.041(7)
N11 0.050(8) 0.032(8) 0.070(8) 0.008(6) -0.007(7) -0.010(6)
N12 0.103(15) 0.089(15) 0.081(11) -0.032(10) 0.044(10) -0.042(12)
N13 0.063(9) 0.067(12) 0.051(7) -0.014(7) 0.017(6) -0.015(8)
N14 0.033(6) 0.069(12) 0.038(6) 0.003(6) 0.004(5) -0.020(6)
N15 0.105(16) 0.099(17) 0.084(11) -0.001(11) 0.021(10) -0.068(13)

_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 N13 2.098(15) . ?
Hg1 N10 2.150(13) . ?
Hg1 N2 2.540(11) . ?
Hg1 N9 2.725(12) . ?
N2 C7 1.326(18) . ?
N2 C3 1.354(19) . ?
C3 C4 1.383(19) . ?
C3 C8 1.506(18) . ?
C4 C5 1.39(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.32(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.40(2) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 N9 1.261(18) . ?
C8 H8 0.9300 . ?
N9 N9 1.36(2) 2_656 ?
N10 N11 1.219(19) . ?
N11 N12 1.15(2) . ?
N13 N14 1.24(2) . ?
N14 N15 1.16(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
N13 Hg1 N10 159.3(6) . . ?
N13 Hg1 N2 105.9(5) . . ?
N10 Hg1 N2 93.3(4) . . ?
N13 Hg1 N9 88.5(5) . . ?
N10 Hg1 N9 107.3(5) . . ?
N2 Hg1 N9 64.2(4) . . ?
C7 N2 C3 117.6(12) . . ?
C7 N2 Hg1 121.5(10) . . ?
C3 N2 Hg1 120.5(8) . . ?
N2 C3 C4 123.4(12) . . ?
N2 C3 C8 116.8(11) . . ?
C4 C3 C8 119.7(14) . . ?
C3 C4 C5 116.6(15) . . ?
C3 C4 H4 121.7 . . ?
C5 C4 H4 121.7 . . ?
C6 C5 C4 120.7(13) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C5 C6 C7 119.9(14) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
N2 C7 C6 121.6(15) . . ?
N2 C7 H7 119.2 . . ?
C6 C7 H7 119.2 . . ?
N9 C8 C3 122.6(14) . . ?
N9 C8 H8 118.7 . . ?
C3 C8 H8 118.7 . . ?
C8 N9 N9 114.5(15) . 2_656 ?
C8 N9 Hg1 114.1(9) . . ?
N9 N9 Hg1 129.0(11) 2_656 . ?
N11 N10 Hg1 114.6(11) . . ?
N12 N11 N10 171.7(19) . . ?
N14 N13 Hg1 116.3(10) . . ?
N15 N14 N13 174.6(16) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 N2 C3 C4 2(2) . . . . ?
Hg1 N2 C3 C4 175.4(10) . . . . ?
C7 N2 C3 C8 178.4(14) . . . . ?
Hg1 N2 C3 C8 -8.5(15) . . . . ?
N2 C3 C4 C5 1(2) . . . . ?
C8 C3 C4 C5 -175.1(12) . . . . ?
C3 C4 C5 C6 -1(2) . . . . ?
C4 C5 C6 C7 -2(2) . . . . ?
C3 N2 C7 C6 -6(3) . . . . ?
Hg1 N2 C7 C6 -178.6(13) . . . . ?
C5 C6 C7 N2 6(3) . . . . ?
N2 C3 C8 N9 -4(2) . . . . ?
C4 C3 C8 N9 172.4(13) . . . . ?
C3 C8 N9 N9 176.5(13) . . . 2_656 ?
C3 C8 N9 Hg1 12.6(17) . . . . ?

_refine_diff_density_max         2.719
_refine_diff_density_min         -2.924
_refine_diff_density_rms         0.364

_shelx_res_file                  
;
TITL scan_0m in P-1
    shelx.res
    created by SHELXL-2018/3 at 12:05:45 on 24-Jul-2020
CELL 0.71073   7.1276   7.8720   9.3576  89.837  82.547  74.782
ZERR    1.00   0.0016   0.0015   0.0021   0.007   0.007   0.007
LATT 1
SFAC C  H  N  Hg
UNIT 12  10  16  2
omit 0 1 0
omit 0 0 1
L.S. 7
ACTA
BOND $H
FMAP 2
PLAN 10
CONF
BIND Hg1 N9
TEMP 27.000

WGHT    0.107400
FVAR       0.54899
HG1   4    0.281230    0.401197    0.449622    11.00000    0.04596    0.03909 =
         0.04223   -0.00531    0.00260   -0.00984
N2    3    0.263342    0.226606    0.226267    11.00000    0.06555    0.03652 =
         0.03865   -0.00667   -0.00611   -0.01506
C3    1    0.320460    0.048297    0.222723    11.00000    0.02401    0.05255 =
         0.03191   -0.00478    0.00202   -0.01276
C4    1    0.301932   -0.054681    0.108548    11.00000    0.02968    0.04434 =
         0.04974   -0.00314    0.00394   -0.01277
AFIX  43
H4    2    0.340820   -0.177040    0.109217    11.00000   -1.20000
AFIX   0
C5    1    0.221945    0.034417   -0.007601    11.00000    0.04431    0.07003 =
         0.03818   -0.01584   -0.00296   -0.01484
AFIX  43
H5    2    0.208081   -0.029294   -0.087309    11.00000   -1.20000
AFIX   0
C6    1    0.165790    0.207881   -0.005666    11.00000    0.05252    0.05712 =
         0.04782    0.00458   -0.01573   -0.01202
AFIX  43
H6    2    0.117158    0.266075   -0.085157    11.00000   -1.20000
AFIX   0
C7    1    0.179412    0.304465    0.116157    11.00000    0.06165    0.03171 =
         0.05754    0.00570   -0.02710    0.01352
AFIX  43
H7    2    0.128390    0.426138    0.119974    11.00000   -1.20000
AFIX   0
C8    1    0.420256   -0.037641    0.346777    11.00000    0.04746    0.02303 =
         0.04978   -0.00043    0.00280   -0.00688
AFIX  43
H8    2    0.454045   -0.159867    0.350155    11.00000   -1.20000
AFIX   0
N9    3    0.459825    0.049541    0.446257    11.00000    0.04393    0.02338 =
         0.04231    0.00289   -0.00602   -0.01376
N10   3    0.488531    0.527170    0.337824    11.00000    0.07028    0.04227 =
         0.06817   -0.01983    0.02245   -0.04117
N11   3    0.575710    0.453091    0.224882    11.00000    0.05044    0.03232 =
         0.06987    0.00785   -0.00658   -0.00997
N12   3    0.673512    0.395657    0.118799    11.00000    0.10270    0.08897 =
         0.08067   -0.03225    0.04427   -0.04234
N13   3    0.062304    0.358691    0.607378    11.00000    0.06257    0.06730 =
         0.05068   -0.01359    0.01687   -0.01534
N14   3    0.060351    0.203506    0.626462    11.00000    0.03333    0.06903 =
         0.03780    0.00306    0.00423   -0.02045
N15   3    0.058582    0.060653    0.655825    11.00000    0.10501    0.09936 =
         0.08394   -0.00088    0.02058   -0.06761
HKLF 4




REM  scan_0m in P-1
REM wR2 = 0.1651, GooF = S = 1.028, Restrained GooF = 1.028 for all data
REM R1 = 0.0596 for 1545 Fo > 4sig(Fo) and 0.0723 for all 1871 data
REM 136 parameters refined using 0 restraints

END

WGHT      0.1074      0.0000

REM Highest difference peak  2.719,  deepest hole -2.924,  1-sigma level  0.364
Q1    1   0.4011  0.4573  0.5017  11.00000  0.05    2.72
Q2    1   0.3983  0.4421  0.4492  11.00000  0.05    2.59
Q3    1   0.1746  0.3372  0.4481  11.00000  0.05    2.42
Q4    1   0.1267  0.3449  0.3262  11.00000  0.05    1.80
Q5    1   0.4068  0.4721  0.3463  11.00000  0.05    1.68
Q6    1   0.4127  0.2860  0.4813  11.00000  0.05    1.30
Q7    1   0.1299  0.3940  0.5478  11.00000  0.05    1.18
Q8    1   0.1228 -0.1846  0.1467  11.00000  0.05    0.97
Q9    1   0.1586 -0.2206  0.6537  11.00000  0.05    0.96
Q10   1   0.4900  0.5413  0.2284  11.00000  0.05    0.92
;
_shelx_res_checksum              92211

loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max

loop_
_publcif_info_exptl_table_header_item
?



_publcif_funding_html            
;
;
