# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 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 2036249'
loop_
_audit_author_name
_audit_author_address
'Damir Safin'
;University of Tyumen
Russia
;
_audit_update_record             
;
2020-10-09 deposited with the CCDC.	2020-11-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H11 Hg I N2 O2 S'
_chemical_formula_sum            'C15 H11 Hg I N2 O2 S'
_chemical_formula_weight         610.81

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'
O O 0.0106 0.0060 '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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C c'
_space_group_name_Hall           'C -2yc'

_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+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   27.761(3)
_cell_length_b                   3.9611(5)
_cell_length_c                   15.6659(16)
_cell_angle_alpha                90
_cell_angle_beta                 111.098(4)
_cell_angle_gamma                90
_cell_volume                     1607.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1371
_cell_measurement_theta_min      2.66
_cell_measurement_theta_max      20.65

_exptl_crystal_description       needle
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.524
_exptl_crystal_F_000             1120
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.153
_exptl_crystal_size_mid          0.029
_exptl_crystal_size_min          0.027
_exptl_absorpt_coefficient_mu    11.634
_shelx_estimated_absorpt_T_min   0.269
_shelx_estimated_absorpt_T_max   0.744
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5846
_exptl_absorpt_correction_T_max  0.7445
_exptl_absorpt_process_details   'SADABS, Bruker 2010'
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7427
_diffrn_reflns_av_unetI/netI     0.1287
_diffrn_reflns_av_R_equivalents  0.0545
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_k_min       -2
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.662
_diffrn_reflns_theta_max         30.587
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.799
_diffrn_reflns_point_group_measured_fraction_full 0.910
_reflns_number_total             3945
_reflns_number_gt                2825
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.668
_reflns_Friedel_fraction_max     0.640
_reflns_Friedel_fraction_full    0.820

_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.
;

_computing_data_collection       'Bruker APEX2 Suite'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Diamond3.2 (Crystal Impact, 2009)'
_computing_publication_material  ?

_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0010P)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_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.114(13)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3945
_refine_ls_number_parameters     200
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0889
_refine_ls_R_factor_gt           0.0506
_refine_ls_wR_factor_ref         0.0886
_refine_ls_wR_factor_gt          0.0781
_refine_ls_goodness_of_fit_ref   0.915
_refine_ls_restrained_S_all      0.915
_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
Hg Hg 0.55664(3) 0.71124(14) 0.74867(3) 0.02647(17) Uani 1 1 d . . . . .
S1 S 0.62120(14) 0.2737(11) 0.7701(3) 0.0230(9) Uani 1 1 d . . . . .
I1 I 0.48034(5) 1.0027(3) 0.78237(9) 0.0318(3) Uani 1 1 d . . . . .
C1 C 0.6278(6) 0.290(4) 0.6608(11) 0.024(4) Uani 1 1 d . . . . .
C2 C 0.6719(6) 0.151(5) 0.6544(10) 0.026(4) Uani 1 1 d . . . . .
H2 H 0.696986 0.052527 0.706982 0.032 Uiso 1 1 calc R U . . .
C3 C 0.6799(6) 0.152(5) 0.5733(11) 0.028(4) Uani 1 1 d . . . . .
H3 H 0.710576 0.055986 0.570217 0.033 Uiso 1 1 calc R U . . .
C4 C 0.6442(8) 0.290(5) 0.4963(13) 0.034(5) Uani 1 1 d . . . . .
H4 H 0.649888 0.288840 0.440087 0.041 Uiso 1 1 calc R U . . .
C5 C 0.5988(6) 0.433(6) 0.5014(12) 0.027(5) Uani 1 1 d . . . . .
H5 H 0.574295 0.534629 0.448770 0.033 Uiso 1 1 calc R U . . .
C6 C 0.5897(6) 0.425(4) 0.5831(11) 0.025(4) Uani 1 1 d . . . . .
N1 N 0.5447(5) 0.563(3) 0.5904(9) 0.022(3) Uani 1 1 d . . . . .
C7 C 0.5015(6) 0.538(5) 0.5230(11) 0.022(4) Uani 1 1 d . . . . .
H7 H 0.500959 0.422258 0.469646 0.027 Uiso 1 1 calc R U . . .
C8 C 0.4548(7) 0.674(5) 0.5240(13) 0.028(5) Uani 1 1 d . . . . .
H8 H 0.455175 0.799038 0.576023 0.034 Uiso 1 1 calc R U . . .
C9 C 0.4099(7) 0.634(5) 0.4543(11) 0.029(4) Uani 1 1 d . . . . .
H9 H 0.409885 0.513697 0.401889 0.034 Uiso 1 1 calc R U . . .
C10 C 0.3605(6) 0.768(5) 0.4550(11) 0.027(4) Uani 1 1 d . . . . .
C11 C 0.3513(7) 0.842(6) 0.5347(14) 0.045(6) Uani 1 1 d . . . . .
H11 H 0.378220 0.803731 0.591880 0.054 Uiso 1 1 calc R U . . .
C12 C 0.3053(7) 0.968(5) 0.5345(13) 0.043(5) Uani 1 1 d . . . . .
H12 H 0.300977 1.022325 0.590398 0.052 Uiso 1 1 calc R U . . .
C13 C 0.2650(7) 1.015(5) 0.4514(14) 0.040(5) Uani 1 1 d . . . . .
H13 H 0.232989 1.102751 0.450462 0.048 Uiso 1 1 calc R U . . .
C14 C 0.2712(7) 0.937(5) 0.3714(13) 0.036(5) Uani 1 1 d . . . . .
H14 H 0.243433 0.963913 0.314623 0.043 Uiso 1 1 calc R U . . .
C15 C 0.3172(6) 0.822(5) 0.3742(11) 0.028(4) Uani 1 1 d . . . . .
N2 N 0.3223(6) 0.760(5) 0.2853(11) 0.045(5) Uani 1 1 d . . . . .
O1 O 0.3597(6) 0.868(5) 0.2744(9) 0.071(5) Uani 1 1 d . . . . .
O2 O 0.2879(6) 0.617(5) 0.2270(9) 0.066(5) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Hg S1 2.428(4) . ?
Hg N1 2.451(13) . ?
Hg I1 2.6273(14) . ?
Hg S1 2.803(4) 1_565 ?
S1 C1 1.788(16) . ?
C1 C2 1.38(2) . ?
C1 C6 1.40(2) . ?
C2 C3 1.37(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.37(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.41(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.39(2) . ?
C5 H5 0.9500 . ?
C6 N1 1.40(2) . ?
N1 C7 1.286(19) . ?
C7 C8 1.41(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.34(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.47(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.39(3) . ?
C10 C15 1.41(2) . ?
C11 C12 1.37(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.39(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.36(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.34(2) . ?
C14 H14 0.9500 . ?
C15 N2 1.47(2) . ?
N2 O1 1.19(2) . ?
N2 O2 1.20(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
S1 Hg N1 78.1(3) . . ?
S1 Hg I1 153.40(10) . . ?
N1 Hg I1 118.9(3) . . ?
S1 Hg S1 98.19(13) . 1_565 ?
N1 Hg S1 99.2(3) . 1_565 ?
I1 Hg S1 98.84(9) . 1_565 ?
C1 S1 Hg 99.6(6) . . ?
C1 S1 Hg 101.3(5) . 1_545 ?
Hg S1 Hg 98.19(13) . 1_545 ?
C2 C1 C6 120.2(15) . . ?
C2 C1 S1 117.1(12) . . ?
C6 C1 S1 122.6(12) . . ?
C3 C2 C1 120.8(15) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C2 C3 C4 120.8(16) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C3 C4 C5 119.3(17) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C6 C5 C4 120.4(17) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C1 118.4(15) . . ?
C5 C6 N1 121.9(14) . . ?
C1 C6 N1 119.7(15) . . ?
C7 N1 C6 119.9(14) . . ?
C7 N1 Hg 126.5(11) . . ?
C6 N1 Hg 112.0(9) . . ?
N1 C7 C8 123.6(15) . . ?
N1 C7 H7 118.2 . . ?
C8 C7 H7 118.2 . . ?
C9 C8 C7 122.4(17) . . ?
C9 C8 H8 118.8 . . ?
C7 C8 H8 118.8 . . ?
C8 C9 C10 123.2(16) . . ?
C8 C9 H9 118.4 . . ?
C10 C9 H9 118.4 . . ?
C11 C10 C15 113.6(15) . . ?
C11 C10 C9 123.6(14) . . ?
C15 C10 C9 122.8(15) . . ?
C12 C11 C10 123.1(17) . . ?
C12 C11 H11 118.4 . . ?
C10 C11 H11 118.4 . . ?
C11 C12 C13 119.0(19) . . ?
C11 C12 H12 120.5 . . ?
C13 C12 H12 120.5 . . ?
C14 C13 C12 120.5(18) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C15 C14 C13 118.8(17) . . ?
C15 C14 H14 120.6 . . ?
C13 C14 H14 120.6 . . ?
C14 C15 C10 125.0(16) . . ?
C14 C15 N2 116.2(15) . . ?
C10 C15 N2 118.8(14) . . ?
O1 N2 O2 123.8(18) . . ?
O1 N2 C15 117.6(17) . . ?
O2 N2 C15 118.5(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
Hg S1 C1 C2 161.1(12) . . . . ?
Hg S1 C1 C2 -98.5(13) 1_545 . . . ?
Hg S1 C1 C6 -21.5(14) . . . . ?
Hg S1 C1 C6 79.0(14) 1_545 . . . ?
C6 C1 C2 C3 2(3) . . . . ?
S1 C1 C2 C3 179.8(14) . . . . ?
C1 C2 C3 C4 0(3) . . . . ?
C2 C3 C4 C5 0(3) . . . . ?
C3 C4 C5 C6 -2(3) . . . . ?
C4 C5 C6 C1 4(3) . . . . ?
C4 C5 C6 N1 -179.5(17) . . . . ?
C2 C1 C6 C5 -4(3) . . . . ?
S1 C1 C6 C5 178.9(14) . . . . ?
C2 C1 C6 N1 179.2(15) . . . . ?
S1 C1 C6 N1 2(2) . . . . ?
C5 C6 N1 C7 37(2) . . . . ?
C1 C6 N1 C7 -146.6(17) . . . . ?
C5 C6 N1 Hg -156.9(14) . . . . ?
C1 C6 N1 Hg 20.0(19) . . . . ?
C6 N1 C7 C8 -178.9(18) . . . . ?
Hg N1 C7 C8 17(3) . . . . ?
N1 C7 C8 C9 -177.4(18) . . . . ?
C7 C8 C9 C10 178.6(18) . . . . ?
C8 C9 C10 C11 -23(3) . . . . ?
C8 C9 C10 C15 159.4(18) . . . . ?
C15 C10 C11 C12 -3(3) . . . . ?
C9 C10 C11 C12 179.7(19) . . . . ?
C10 C11 C12 C13 2(3) . . . . ?
C11 C12 C13 C14 0(3) . . . . ?
C12 C13 C14 C15 -2(3) . . . . ?
C13 C14 C15 C10 1(3) . . . . ?
C13 C14 C15 N2 -176.7(17) . . . . ?
C11 C10 C15 C14 1(3) . . . . ?
C9 C10 C15 C14 178.7(18) . . . . ?
C11 C10 C15 N2 178.6(18) . . . . ?
C9 C10 C15 N2 -4(3) . . . . ?
C14 C15 N2 O1 132.5(19) . . . . ?
C10 C15 N2 O1 -45(3) . . . . ?
C14 C15 N2 O2 -44(3) . . . . ?
C10 C15 N2 O2 137.6(19) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C2 H2 O2 0.95 2.52 3.19(2) 127.3 4 yes
C7 H7 I1 0.95 3.25 4.190(16) 170.9 2_564 yes
C8 H8 I1 0.95 3.16 4.06(2) 160.4 . yes

_refine_diff_density_max         1.775
_refine_diff_density_min         -2.040
_refine_diff_density_rms         0.271

####################################################################### 
# 
# 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_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2040554'
loop_
_audit_author_name
_audit_author_address
'Damir Safin'
;University of Tyumen
Russia
;
_audit_update_record             
;
2020-10-26 deposited with the CCDC.	2020-11-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H10 Hg I2 N4 O3'
_chemical_formula_weight         724.64
_chemical_oxdiff_usercomment     'Prof Montazerozohori sample M7'

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'
O O 0.0106 0.0060 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   4.59420(10)
_cell_length_b                   28.1575(9)
_cell_length_c                   13.2262(3)
_cell_angle_alpha                90
_cell_angle_beta                 93.104(2)
_cell_angle_gamma                90
_cell_volume                     1708.45(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    130(1)
_cell_measurement_reflns_used    6461
_cell_measurement_theta_min      3.77
_cell_measurement_theta_max      34.07

_exptl_crystal_description       rod
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.817
_exptl_crystal_F_000             1304
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.5504
_exptl_crystal_size_mid          0.1269
_exptl_crystal_size_min          0.0656
_exptl_absorpt_coefficient_mu    12.641
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.079
_exptl_absorpt_correction_T_max  0.451
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      130(1)
_diffrn_ambient_environment      air
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.2273
_diffrn_reflns_number            17349
_diffrn_reflns_av_unetI/netI     0.0700
_diffrn_reflns_av_R_equivalents  0.0575
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -42
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.408
_diffrn_reflns_theta_max         34.295
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.930
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.930
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.930
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             6625
_reflns_number_gt                5224
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_structure_solution    SHELXT
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0572P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6625
_refine_ls_number_parameters     212
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0574
_refine_ls_R_factor_gt           0.0414
_refine_ls_wR_factor_ref         0.1120
_refine_ls_wR_factor_gt          0.0988
_refine_ls_goodness_of_fit_ref   0.885
_refine_ls_restrained_S_all      0.885
_refine_ls_shift/su_max          0.007
_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
C1 C 0.7506(11) 0.6894(2) 0.8555(4) 0.0215(10) Uani 1 1 d . . . . .
H1 H 0.8882 0.7135 0.8508 0.026 Uiso 1 1 calc R U . . .
C2 C 0.6666(11) 0.6640(2) 0.7695(3) 0.0217(10) Uani 1 1 d . . . . .
H2 H 0.7480 0.6706 0.7082 0.026 Uiso 1 1 calc R U . . .
C3 C 0.4590(10) 0.62844(18) 0.7757(3) 0.0179(9) Uani 1 1 d . . . . .
C4 C 0.3476(11) 0.61921(19) 0.8687(4) 0.0209(9) Uani 1 1 d . . . . .
H4 H 0.2083 0.5956 0.8754 0.025 Uiso 1 1 calc R U . . .
C5 C 0.4462(11) 0.6455(2) 0.9512(4) 0.0253(11) Uani 1 1 d . . . . .
H5 H 0.3747 0.6386 1.0140 0.030 Uiso 1 1 calc R U . . .
C6 C 0.3388(10) 0.60168(18) 0.6837(3) 0.0174(9) Uani 1 1 d . . . . .
C7 C 0.6268(11) 0.57865(19) 0.4524(4) 0.0204(9) Uani 1 1 d . . . . .
H7 H 0.8016 0.5945 0.4670 0.025 Uiso 1 1 calc R U . . .
C8 C 0.5732(10) 0.55605(19) 0.3530(4) 0.0205(9) Uani 1 1 d . . . . .
C9 C 0.7321(10) 0.5728(2) 0.2735(3) 0.0199(9) Uani 1 1 d . . . . .
H9 H 0.8663 0.5973 0.2832 0.024 Uiso 1 1 calc R U . . .
C10 C 0.6835(11) 0.55169(19) 0.1798(4) 0.0200(9) Uani 1 1 d . . . . .
C11 C 0.4887(11) 0.5152(2) 0.1600(4) 0.0223(10) Uani 1 1 d . . . . .
H11 H 0.4633 0.5019 0.0958 0.027 Uiso 1 1 calc R U . . .
C12 C 0.3300(11) 0.4991(2) 0.2411(4) 0.0231(10) Uani 1 1 d . . . . .
H12 H 0.1977 0.4743 0.2309 0.028 Uiso 1 1 calc R U . . .
C13 C 0.3675(11) 0.51939(18) 0.3352(4) 0.0194(9) Uani 1 1 d . . . . .
H13 H 0.2566 0.5089 0.3876 0.023 Uiso 1 1 calc R U . . .
N1 N 0.6414(9) 0.68077(17) 0.9449(3) 0.0218(8) Uani 1 1 d . . . . .
N2 N 0.5229(9) 0.59827(16) 0.6079(3) 0.0178(8) Uani 1 1 d . . . . .
N3 N 0.4352(9) 0.57673(17) 0.5192(3) 0.0201(8) Uani 1 1 d . . . . .
N4 N 0.8507(10) 0.56955(19) 0.0960(3) 0.0281(10) Uani 1 1 d . . . . .
O1 O 0.0905(7) 0.58569(15) 0.6804(3) 0.0237(8) Uani 1 1 d . . . . .
O2 O 1.0058(10) 0.60464(19) 0.1122(3) 0.0415(11) Uani 1 1 d . . . . .
O3 O 0.8322(10) 0.54903(19) 0.0151(3) 0.0391(11) Uani 1 1 d . . . . .
I1 I 0.44393(8) 0.69711(2) 1.23296(2) 0.02655(9) Uani 1 1 d . . . . .
I2 I 1.10130(7) 0.79475(2) 1.01081(2) 0.02362(9) Uani 1 1 d . . . . .
Hg1 Hg 0.75261(5) 0.73147(2) 1.08884(2) 0.02643(7) Uani 1 1 d . . . . .
H2A H 0.700(12) 0.605(2) 0.616(4) 0.016(14) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.332(6) . ?
C1 C2 1.382(7) . ?
C1 H1 0.9300 . ?
C2 C3 1.389(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.382(7) . ?
C3 C6 1.511(6) . ?
C4 C5 1.375(7) . ?
C4 H4 0.9300 . ?
C5 N1 1.343(7) . ?
C5 H5 0.9300 . ?
C6 O1 1.225(6) . ?
C6 N2 1.349(6) . ?
C7 N3 1.282(6) . ?
C7 C8 1.470(7) . ?
C7 H7 0.9300 . ?
C8 C9 1.394(7) . ?
C8 C13 1.410(7) . ?
C9 C10 1.381(7) . ?
C9 H9 0.9300 . ?
C10 C11 1.378(7) . ?
C10 N4 1.470(7) . ?
C11 C12 1.405(7) . ?
C11 H11 0.9300 . ?
C12 C13 1.372(7) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
N1 Hg1 2.412(4) . ?
N2 N3 1.362(5) . ?
N2 H2A 0.84(6) . ?
N4 O3 1.216(6) . ?
N4 O2 1.230(7) . ?
I1 Hg1 2.6218(4) . ?
I2 Hg1 2.6430(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 122.3(5) . . ?
N1 C1 H1 118.8 . . ?
C2 C1 H1 118.8 . . ?
C1 C2 C3 119.1(4) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 H2 120.4 . . ?
C4 C3 C2 118.5(5) . . ?
C4 C3 C6 119.1(4) . . ?
C2 C3 C6 122.3(4) . . ?
C5 C4 C3 118.8(5) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
N1 C5 C4 122.8(5) . . ?
N1 C5 H5 118.6 . . ?
C4 C5 H5 118.6 . . ?
O1 C6 N2 124.6(4) . . ?
O1 C6 C3 120.7(4) . . ?
N2 C6 C3 114.7(4) . . ?
N3 C7 C8 120.7(5) . . ?
N3 C7 H7 119.7 . . ?
C8 C7 H7 119.7 . . ?
C9 C8 C13 119.6(5) . . ?
C9 C8 C7 117.4(5) . . ?
C13 C8 C7 123.0(4) . . ?
C10 C9 C8 117.8(5) . . ?
C10 C9 H9 121.1 . . ?
C8 C9 H9 121.1 . . ?
C11 C10 C9 124.2(5) . . ?
C11 C10 N4 118.2(4) . . ?
C9 C10 N4 117.6(5) . . ?
C10 C11 C12 117.0(5) . . ?
C10 C11 H11 121.5 . . ?
C12 C11 H11 121.5 . . ?
C13 C12 C11 120.9(5) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C12 C13 C8 120.4(5) . . ?
C12 C13 H13 119.8 . . ?
C8 C13 H13 119.8 . . ?
C1 N1 C5 118.4(4) . . ?
C1 N1 Hg1 121.2(4) . . ?
C5 N1 Hg1 120.1(3) . . ?
C6 N2 N3 120.2(4) . . ?
C6 N2 H2A 122(4) . . ?
N3 N2 H2A 117(4) . . ?
C7 N3 N2 113.1(4) . . ?
O3 N4 O2 123.2(5) . . ?
O3 N4 C10 119.1(5) . . ?
O2 N4 C10 117.7(4) . . ?
N1 Hg1 I1 104.80(10) . . ?
N1 Hg1 I2 101.41(10) . . ?
I1 Hg1 I2 153.624(14) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 0.7(8) . . . . ?
C1 C2 C3 C4 -1.1(8) . . . . ?
C1 C2 C3 C6 175.2(5) . . . . ?
C2 C3 C4 C5 0.0(8) . . . . ?
C6 C3 C4 C5 -176.4(5) . . . . ?
C3 C4 C5 N1 1.7(8) . . . . ?
C4 C3 C6 O1 25.9(7) . . . . ?
C2 C3 C6 O1 -150.3(5) . . . . ?
C4 C3 C6 N2 -155.4(5) . . . . ?
C2 C3 C6 N2 28.4(7) . . . . ?
N3 C7 C8 C9 157.8(5) . . . . ?
N3 C7 C8 C13 -21.1(8) . . . . ?
C13 C8 C9 C10 -1.1(7) . . . . ?
C7 C8 C9 C10 179.9(5) . . . . ?
C8 C9 C10 C11 -0.1(8) . . . . ?
C8 C9 C10 N4 179.7(5) . . . . ?
C9 C10 C11 C12 0.4(8) . . . . ?
N4 C10 C11 C12 -179.5(5) . . . . ?
C10 C11 C12 C13 0.6(8) . . . . ?
C11 C12 C13 C8 -1.9(8) . . . . ?
C9 C8 C13 C12 2.1(8) . . . . ?
C7 C8 C13 C12 -179.0(5) . . . . ?
C2 C1 N1 C5 1.0(8) . . . . ?
C2 C1 N1 Hg1 -173.1(4) . . . . ?
C4 C5 N1 C1 -2.2(8) . . . . ?
C4 C5 N1 Hg1 171.9(4) . . . . ?
O1 C6 N2 N3 1.5(8) . . . . ?
C3 C6 N2 N3 -177.2(4) . . . . ?
C8 C7 N3 N2 178.2(5) . . . . ?
C6 N2 N3 C7 176.1(5) . . . . ?
C11 C10 N4 O3 -6.7(8) . . . . ?
C9 C10 N4 O3 173.5(5) . . . . ?
C11 C10 N4 O2 174.0(5) . . . . ?
C9 C10 N4 O2 -5.8(8) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C1 H1 I2 0.93 3.23 3.905(5) 130.9 .
C2 H2 I2 0.93 3.29 4.217(5) 171.3 4_575
C5 H5 O2 0.93 2.39 3.228(7) 149.7 1_456
C11 H11 O3 0.93 2.42 3.231(7) 146.3 3_665
N2 H2A O1 0.84(6) 2.03(6) 2.752(5) 145(6) 1_655
C1 H1 I2 0.93 3.23 3.905(5) 130.9 .
C2 H2 I2 0.93 3.29 4.217(5) 171.3 4_575
C5 H5 O2 0.93 2.39 3.228(7) 149.7 1_456
C11 H11 O3 0.93 2.42 3.231(7) 146.3 3_665
N2 H2A O1 0.84(6) 2.03(6) 2.752(5) 145(6) 1_655

_refine_diff_density_max         2.721
_refine_diff_density_min         -2.993
_refine_diff_density_rms         0.302

