# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1583981'
_audit_update_record             
;
2017-11-04 deposited with the CCDC.
2018-01-09 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         'C13 H12 Br4 Hg2 N4 O'
_chemical_formula_sum            'C13 H12 Br4 Hg2 N4 O'
_chemical_formula_weight         961.09

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'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   8.7230(15)
_cell_length_b                   14.244(2)
_cell_length_c                   16.507(3)
_cell_angle_alpha                90
_cell_angle_beta                 100.782(3)
_cell_angle_gamma                90
_cell_volume                     2014.8(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    193(1)
_cell_measurement_reflns_used    3300
_cell_measurement_theta_min      5
_cell_measurement_theta_max      24

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    3.168
_exptl_crystal_F_000             1704
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.210
_exptl_absorpt_coefficient_mu    23.163
_shelx_estimated_absorpt_T_min   0.050
_shelx_estimated_absorpt_T_max   0.085
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3223
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'SADABS, Bruker-AXS, 2010'
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      193(1)
_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_number            13846
_diffrn_reflns_av_unetI/netI     0.0532
_diffrn_reflns_av_R_equivalents  0.0606
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.903
_diffrn_reflns_theta_max         25.090
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measured_fraction_theta_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_point_group_measured_fraction_full 0.980
_reflns_number_total             3496
_reflns_number_gt                2881
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Mercury (MacRae et al., 2009)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'


_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)+(0.0355P)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         3496
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0447
_refine_ls_R_factor_gt           0.0323
_refine_ls_wR_factor_ref         0.0776
_refine_ls_wR_factor_gt          0.0734
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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 -0.21377(4) 0.56213(2) 0.15367(2) 0.02581(11) Uani 1 1 d . . . . .
Hg2 Hg -0.16138(4) 0.83575(2) 0.07571(2) 0.02386(11) Uani 1 1 d . . . . .
Br1 Br -0.28604(15) 0.41164(7) 0.08656(7) 0.0521(3) Uani 1 1 d . . . . .
Br2 Br -0.25189(10) 0.69718(6) 0.24292(5) 0.0284(2) Uani 1 1 d . . . . .
Br3 Br -0.24146(15) 0.68049(7) 0.00746(6) 0.0492(3) Uani 1 1 d . . . . .
Br4 Br -0.27748(10) 0.96022(6) 0.15198(6) 0.0305(2) Uani 1 1 d . . . . .
N1 N 0.5964(7) 0.6713(4) 0.6542(4) 0.0199(15) Uani 1 1 d . . . . .
C2 C 0.6205(11) 0.6772(5) 0.7360(5) 0.025(2) Uani 1 1 d . . . . .
H2 H 0.5326 0.6810 0.7622 0.030 Uiso 1 1 calc R U . . .
C3 C 0.7666(11) 0.6780(6) 0.7838(5) 0.029(2) Uani 1 1 d . . . . .
H3 H 0.7800 0.6825 0.8422 0.035 Uiso 1 1 calc R U . . .
C4 C 0.8936(11) 0.6721(5) 0.7458(5) 0.029(2) Uani 1 1 d . . . . .
H4 H 0.9963 0.6713 0.7776 0.034 Uiso 1 1 calc R U . . .
C5 C 0.8697(10) 0.6674(5) 0.6604(5) 0.0237(19) Uani 1 1 d . . . . .
H5 H 0.9560 0.6660 0.6329 0.028 Uiso 1 1 calc R U . . .
C6 C 0.7182(9) 0.6647(5) 0.6158(5) 0.0171(17) Uani 1 1 d . . . . .
C7 C 0.6868(9) 0.6516(5) 0.5243(5) 0.0182(17) Uani 1 1 d . . . . .
C71 C 0.8202(10) 0.6643(7) 0.4795(5) 0.032(2) Uani 1 1 d . . . . .
H71A H 0.8906 0.6102 0.4901 0.048 Uiso 1 1 calc R U . . .
H71B H 0.8774 0.7217 0.4989 0.048 Uiso 1 1 calc R U . . .
H71C H 0.7796 0.6692 0.4201 0.048 Uiso 1 1 calc R U . . .
N8 N 0.5460(7) 0.6297(4) 0.4945(4) 0.0151(14) Uani 1 1 d . . . . .
N9 N 0.4981(7) 0.6141(5) 0.4109(4) 0.0203(15) Uani 1 1 d . . . . .
H9 H 0.5627 0.6200 0.3762 0.024 Uiso 1 1 calc R U . . .
C10 C 0.3459(9) 0.5889(5) 0.3849(5) 0.0195(18) Uani 1 1 d . . . . .
O10 O 0.2543(7) 0.5817(4) 0.4319(4) 0.0328(15) Uani 1 1 d . . . . .
C11 C 0.2946(9) 0.5743(5) 0.2949(5) 0.0161(17) Uani 1 1 d . . . . .
C12 C 0.1343(9) 0.5740(5) 0.2672(5) 0.0210(18) Uani 1 1 d . . . . .
H12 H 0.0681 0.5811 0.3064 0.025 Uiso 1 1 calc R U . . .
N13 N 0.0685(8) 0.5641(5) 0.1869(4) 0.0250(16) Uani 1 1 d . . . . .
C14 C 0.1639(10) 0.5535(6) 0.1313(5) 0.027(2) Uani 1 1 d . . . . .
H14 H 0.1193 0.5474 0.0745 0.032 Uiso 1 1 calc R U . . .
C15 C 0.3219(10) 0.5516(7) 0.1551(5) 0.032(2) Uani 1 1 d . . . . .
H15 H 0.3859 0.5444 0.1149 0.038 Uiso 1 1 calc R U . . .
C16 C 0.3896(9) 0.5599(6) 0.2372(5) 0.025(2) Uani 1 1 d . . . . .
H16 H 0.4997 0.5558 0.2541 0.030 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Hg1 N13 2.420(7) . ?
Hg1 Br1 2.4409(11) . ?
Hg1 Br2 2.4829(9) . ?
Hg1 Br3 2.9168(11) . ?
Hg2 N1 2.378(6) 4_575 ?
Hg2 N8 2.494(6) 4_575 ?
Hg2 Br4 2.4962(9) . ?
Hg2 Br3 2.5206(10) . ?
Hg2 O10 2.628(6) 4_575 ?
N1 C2 1.329(10) . ?
N1 C6 1.339(10) . ?
N1 Hg2 2.378(6) 4_676 ?
C2 C3 1.369(12) . ?
C2 H2 0.9500 . ?
C3 C4 1.373(13) . ?
C3 H3 0.9500 . ?
C4 C5 1.387(11) . ?
C4 H4 0.9500 . ?
C5 C6 1.388(11) . ?
C5 H5 0.9500 . ?
C6 C7 1.494(11) . ?
C7 N8 1.274(9) . ?
C7 C71 1.503(11) . ?
C71 H71A 0.9800 . ?
C71 H71B 0.9800 . ?
C71 H71C 0.9800 . ?
N8 N9 1.382(8) . ?
N8 Hg2 2.494(6) 4_676 ?
N9 C10 1.365(10) . ?
N9 H9 0.8800 . ?
C10 O10 1.218(10) . ?
C10 C11 1.484(11) . ?
O10 Hg2 2.628(6) 4_676 ?
C11 C12 1.387(11) . ?
C11 C16 1.390(11) . ?
C12 N13 1.349(10) . ?
C12 H12 0.9500 . ?
N13 C14 1.358(11) . ?
C14 C15 1.361(12) . ?
C14 H14 0.9500 . ?
C15 C16 1.378(11) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?

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 Br1 106.17(16) . . ?
N13 Hg1 Br2 95.73(16) . . ?
Br1 Hg1 Br2 153.87(4) . . ?
N13 Hg1 Br3 95.99(17) . . ?
Br1 Hg1 Br3 99.08(4) . . ?
Br2 Hg1 Br3 92.50(3) . . ?
N1 Hg2 N8 66.1(2) 4_575 4_575 ?
N1 Hg2 Br4 100.75(16) 4_575 . ?
N8 Hg2 Br4 122.32(14) 4_575 . ?
N1 Hg2 Br3 111.19(16) 4_575 . ?
N8 Hg2 Br3 95.79(14) 4_575 . ?
Br4 Hg2 Br3 138.07(4) . . ?
N1 Hg2 O10 126.0(2) 4_575 4_575 ?
N8 Hg2 O10 62.26(19) 4_575 4_575 ?
Br4 Hg2 O10 93.81(13) . 4_575 ?
Br3 Hg2 O10 88.94(14) . 4_575 ?
Hg2 Br3 Hg1 99.45(3) . . ?
C2 N1 C6 119.8(7) . . ?
C2 N1 Hg2 120.6(5) . 4_676 ?
C6 N1 Hg2 119.5(5) . 4_676 ?
N1 C2 C3 122.7(8) . . ?
N1 C2 H2 118.7 . . ?
C3 C2 H2 118.7 . . ?
C4 C3 C2 118.6(8) . . ?
C4 C3 H3 120.7 . . ?
C2 C3 H3 120.7 . . ?
C3 C4 C5 119.1(8) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C6 C5 C4 119.2(8) . . ?
C6 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?
N1 C6 C5 120.5(7) . . ?
N1 C6 C7 118.4(7) . . ?
C5 C6 C7 121.1(7) . . ?
N8 C7 C6 113.8(7) . . ?
N8 C7 C71 128.2(7) . . ?
C6 C7 C71 118.1(7) . . ?
C7 C71 H71A 109.5 . . ?
C7 C71 H71B 109.5 . . ?
H71A C71 H71B 109.5 . . ?
C7 C71 H71C 109.5 . . ?
H71A C71 H71C 109.5 . . ?
H71B C71 H71C 109.5 . . ?
C7 N8 N9 121.0(6) . . ?
C7 N8 Hg2 119.2(5) . 4_676 ?
N9 N8 Hg2 117.0(4) . 4_676 ?
C10 N9 N8 116.9(6) . . ?
C10 N9 H9 121.6 . . ?
N8 N9 H9 121.6 . . ?
O10 C10 N9 122.4(7) . . ?
O10 C10 C11 121.0(7) . . ?
N9 C10 C11 116.5(7) . . ?
C10 O10 Hg2 115.6(5) . 4_676 ?
C12 C11 C16 117.9(7) . . ?
C12 C11 C10 115.2(7) . . ?
C16 C11 C10 126.9(7) . . ?
N13 C12 C11 122.8(8) . . ?
N13 C12 H12 118.6 . . ?
C11 C12 H12 118.6 . . ?
C12 N13 C14 118.2(7) . . ?
C12 N13 Hg1 116.9(5) . . ?
C14 N13 Hg1 124.8(5) . . ?
N13 C14 C15 121.5(8) . . ?
N13 C14 H14 119.2 . . ?
C15 C14 H14 119.2 . . ?
C14 C15 C16 120.5(8) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C15 C16 C11 119.0(8) . . ?
C15 C16 H16 120.5 . . ?
C11 C16 H16 120.5 . . ?

_refine_diff_density_max         1.101
_refine_diff_density_min         -1.635
_refine_diff_density_rms         0.277

####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 1583983'
_audit_update_record             
;
2017-11-04 deposited with the CCDC.
2018-01-09 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         'C13 H12 Hg I2 N4 O'
_chemical_formula_sum            'C13 H12 Hg I2 N4 O'
_chemical_formula_weight         694.66

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'
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'
O O 0.0106 0.0060 '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                   9.4971(10)
_cell_length_b                   19.796(2)
_cell_length_c                   9.2661(10)
_cell_angle_alpha                90
_cell_angle_beta                 96.913(10)
_cell_angle_gamma                90
_cell_volume                     1729.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    2442
_cell_measurement_theta_min      4
_cell_measurement_theta_max      27

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.668
_exptl_crystal_F_000             1248
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_exptl_absorpt_coefficient_mu    12.473
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   numerical

_exptl_absorpt_process_details   sadabs

_exptl_absorpt_correction_T_min  0.027

_exptl_absorpt_correction_T_max  0.222

_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'Nonius CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_number            75755
_diffrn_reflns_av_R_equivalents  0.0464

_diffrn_reflns_av_sigmaI/netI    0.0262
_diffrn_reflns_limit_h_min       -12

_diffrn_reflns_limit_h_max       12

_diffrn_reflns_limit_k_min       -26

_diffrn_reflns_limit_k_max       26

_diffrn_reflns_limit_l_min       -12

_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.057
_diffrn_reflns_theta_max         28.000
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4179
_reflns_number_gt                3652
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Mercury (MacRae et al., 2009)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'

_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)+(0.0106P)²+1.6142P] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.00304(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4179
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0352
_refine_ls_R_factor_gt           0.0254
_refine_ls_wR_factor_ref         0.0779
_refine_ls_wR_factor_gt          0.0753
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.002
_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 0.83573(2) 0.88269(2) 0.74169(2) 0.03713(8) Uani 1 1 d . . . . .
I1 I 0.86334(4) 0.75416(2) 0.82032(5) 0.05314(12) Uani 1 1 d . . . . .
I2 I 0.64632(4) 0.97439(2) 0.80285(4) 0.04818(11) Uani 1 1 d . . . . .
N1 N 0.8493(4) 0.9158(2) 0.4915(4) 0.0342(8) Uani 1 1 d . . . . .
C2 C 0.7354(5) 0.9326(3) 0.4002(6) 0.0412(11) Uani 1 1 d . . . . .
H2 H 0.6475 0.9338 0.4350 0.049 Uiso 1 1 calc R U . . .
C3 C 0.7424(6) 0.9484(3) 0.2557(6) 0.0456(12) Uani 1 1 d . . . . .
H3 H 0.6606 0.9595 0.1947 0.055 Uiso 1 1 calc R U . . .
C4 C 0.8685(6) 0.9476(3) 0.2051(5) 0.0395(11) Uani 1 1 d . . . . .
H4 H 0.8752 0.9577 0.1081 0.047 Uiso 1 1 calc R U . . .
C5 C 0.9889(5) 0.9314(2) 0.2983(5) 0.0343(9) Uani 1 1 d . . . . .
H5 H 1.0775 0.9314 0.2650 0.041 Uiso 1 1 calc R U . . .
C6 C 0.9760(5) 0.9155(2) 0.4406(4) 0.0278(8) Uani 1 1 d . . . . .
C7 C 1.1009(5) 0.8971(2) 0.5452(5) 0.0289(8) Uani 1 1 d . . . . .
C71 C 1.2401(6) 0.8860(3) 0.4923(6) 0.0461(13) Uani 1 1 d . . . . .
H71A H 1.3136 0.8869 0.5731 0.069 Uiso 1 1 calc R U . . .
H71B H 1.2568 0.9211 0.4248 0.069 Uiso 1 1 calc R U . . .
H71C H 1.2402 0.8430 0.4447 0.069 Uiso 1 1 calc R U . . .
N8 N 1.0763(4) 0.89257(19) 0.6776(4) 0.0286(7) Uani 1 1 d . . . . .
N9 N 1.1831(4) 0.8702(2) 0.7803(4) 0.0285(7) Uani 1 1 d . . . . .
H9 H 1.2611 0.8541 0.7560 0.034 Uiso 1 1 calc R U . . .
C10 C 1.1595(5) 0.8746(2) 0.9206(5) 0.0286(8) Uani 1 1 d . . . . .
O10 O 1.0604(4) 0.9046(2) 0.9623(4) 0.0394(8) Uani 1 1 d . . . . .
C11 C 1.2692(5) 0.8378(2) 1.0192(5) 0.0297(8) Uani 1 1 d . . . . .
C12 C 1.2256(5) 0.7921(3) 1.1171(5) 0.0365(10) Uani 1 1 d . . . . .
H12 H 1.1292 0.7884 1.1247 0.044 Uiso 1 1 calc R U . . .
N13 N 1.3160(5) 0.7528(3) 1.2020(5) 0.0452(11) Uani 1 1 d . . . . .
C14 C 1.4540(6) 0.7623(3) 1.1930(7) 0.0501(14) Uani 1 1 d . . . . .
H14 H 1.5186 0.7369 1.2540 0.060 Uiso 1 1 calc R U . . .
C15 C 1.5063(6) 0.8066(3) 1.1006(7) 0.0487(13) Uani 1 1 d . . . . .
H15 H 1.6035 0.8108 1.0983 0.058 Uiso 1 1 calc R U . . .
C16 C 1.4125(5) 0.8451(3) 1.0110(6) 0.0421(11) Uani 1 1 d . . . . .
H16 H 1.4450 0.8754 0.9459 0.051 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Hg1 N1 2.427(4) . ?
Hg1 N8 2.436(4) . ?
Hg1 I1 2.6510(5) . ?
Hg1 I2 2.6642(5) . ?
N1 C2 1.333(6) . ?
N1 C6 1.344(6) . ?
C2 C3 1.384(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.338(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.385(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.376(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.485(6) . ?
C7 N8 1.279(6) . ?
C7 C71 1.481(7) . ?
C71 H71A 0.9600 . ?
C71 H71B 0.9600 . ?
C71 H71C 0.9600 . ?
N8 N9 1.378(5) . ?
N9 C10 1.349(5) . ?
N9 H9 0.8600 . ?
C10 O10 1.215(6) . ?
C10 C11 1.489(6) . ?
C11 C12 1.380(6) . ?
C11 C16 1.380(7) . ?
C12 N13 1.341(7) . ?
C12 H12 0.9300 . ?
N13 C14 1.336(7) . ?
C14 C15 1.361(8) . ?
C14 H14 0.9300 . ?
C15 C16 1.373(8) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Hg1 N8 65.56(13) . . ?
N1 Hg1 I1 120.45(10) . . ?
N8 Hg1 I1 94.56(9) . . ?
N1 Hg1 I2 97.70(10) . . ?
N8 Hg1 I2 132.38(9) . . ?
I1 Hg1 I2 129.978(16) . . ?
C2 N1 C6 118.0(4) . . ?
C2 N1 Hg1 122.8(3) . . ?
C6 N1 Hg1 119.1(3) . . ?
N1 C2 C3 122.7(5) . . ?
N1 C2 H2 118.6 . . ?
C3 C2 H2 118.6 . . ?
C4 C3 C2 119.1(5) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
C3 C4 C5 119.4(5) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C6 C5 C4 119.2(5) . . ?
C6 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?
N1 C6 C5 121.5(4) . . ?
N1 C6 C7 116.8(4) . . ?
C5 C6 C7 121.7(4) . . ?
N8 C7 C71 125.5(4) . . ?
N8 C7 C6 114.8(4) . . ?
C71 C7 C6 119.7(4) . . ?
C7 C71 H71A 109.5 . . ?
C7 C71 H71B 109.5 . . ?
H71A C71 H71B 109.5 . . ?
C7 C71 H71C 109.5 . . ?
H71A C71 H71C 109.5 . . ?
H71B C71 H71C 109.5 . . ?
C7 N8 N9 118.7(4) . . ?
C7 N8 Hg1 121.6(3) . . ?
N9 N8 Hg1 116.1(3) . . ?
C10 N9 N8 116.8(4) . . ?
C10 N9 H9 121.6 . . ?
N8 N9 H9 121.6 . . ?
O10 C10 N9 124.2(4) . . ?
O10 C10 C11 123.7(4) . . ?
N9 C10 C11 112.0(4) . . ?
C12 C11 C16 118.7(4) . . ?
C12 C11 C10 118.7(4) . . ?
C16 C11 C10 122.5(4) . . ?
N13 C12 C11 123.0(5) . . ?
N13 C12 H12 118.5 . . ?
C11 C12 H12 118.5 . . ?
C14 N13 C12 116.5(5) . . ?
N13 C14 C15 124.4(5) . . ?
N13 C14 H14 117.8 . . ?
C15 C14 H14 117.8 . . ?
C14 C15 C16 118.7(5) . . ?
C14 C15 H15 120.7 . . ?
C16 C15 H15 120.7 . . ?
C15 C16 C11 118.8(5) . . ?
C15 C16 H16 120.6 . . ?
C11 C16 H16 120.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 N1 C2 C3 1.2(8) . . . . ?
Hg1 N1 C2 C3 -176.9(4) . . . . ?
N1 C2 C3 C4 -0.7(9) . . . . ?
C2 C3 C4 C5 -0.5(9) . . . . ?
C3 C4 C5 C6 1.1(8) . . . . ?
C2 N1 C6 C5 -0.5(7) . . . . ?
Hg1 N1 C6 C5 177.6(3) . . . . ?
C2 N1 C6 C7 179.5(5) . . . . ?
Hg1 N1 C6 C7 -2.3(5) . . . . ?
C4 C5 C6 N1 -0.6(7) . . . . ?
C4 C5 C6 C7 179.4(4) . . . . ?
N1 C6 C7 N8 -9.2(6) . . . . ?
C5 C6 C7 N8 170.8(4) . . . . ?
N1 C6 C7 C71 171.2(5) . . . . ?
C5 C6 C7 C71 -8.8(7) . . . . ?
C71 C7 N8 N9 -5.9(7) . . . . ?
C6 C7 N8 N9 174.6(4) . . . . ?
C71 C7 N8 Hg1 -163.7(4) . . . . ?
C6 C7 N8 Hg1 16.8(5) . . . . ?
C7 N8 N9 C10 171.5(4) . . . . ?
Hg1 N8 N9 C10 -29.5(5) . . . . ?
N8 N9 C10 O10 -10.1(7) . . . . ?
N8 N9 C10 C11 169.6(4) . . . . ?
O10 C10 C11 C12 50.9(7) . . . . ?
N9 C10 C11 C12 -128.8(5) . . . . ?
O10 C10 C11 C16 -132.7(6) . . . . ?
N9 C10 C11 C16 47.6(6) . . . . ?
C16 C11 C12 N13 -2.1(8) . . . . ?
C10 C11 C12 N13 174.5(5) . . . . ?
C11 C12 N13 C14 3.4(9) . . . . ?
C12 N13 C14 C15 -2.7(10) . . . . ?
N13 C14 C15 C16 0.7(11) . . . . ?
C14 C15 C16 C11 0.8(10) . . . . ?
C12 C11 C16 C15 -0.1(8) . . . . ?
C10 C11 C16 C15 -176.5(5) . . . . ?

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
N9 H9 N13 0.86 2.25 2.875(6) 129.4 4_575

_refine_diff_density_max         1.589
_refine_diff_density_min         -1.311
_refine_diff_density_rms         0.116

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

data_2
_database_code_depnum_ccdc_archive 'CCDC 1583982'
_audit_update_record             
;
2017-11-04 deposited with the CCDC.
2018-01-09 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         'C18 H13 Br Hg N4 O'
_chemical_formula_sum            'C18 H13 Br Hg N4 O'
_chemical_formula_weight         581.82

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'
O O 0.0106 0.0060 '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/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   10.8009(10)
_cell_length_b                   15.0130(13)
_cell_length_c                   11.3474(10)
_cell_angle_alpha                90
_cell_angle_beta                 108.659(2)
_cell_angle_gamma                90
_cell_volume                     1743.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    2988
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      25.00

_exptl_crystal_description       Plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.217
_exptl_crystal_F_000             1088
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    11.134
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3511
_exptl_absorpt_correction_T_max  0.6531
_exptl_absorpt_process_details   'Bruker SAINT'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      295(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  'Bruker Smart APEX CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_number            33100
_diffrn_reflns_av_unetI/netI     0.0451
_diffrn_reflns_av_R_equivalents  0.0657
_diffrn_reflns_limit_h_min       ?
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       ?
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       ?
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.267
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3419
_reflns_number_gt                2709
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Data were apparently pre-merged, so _diffrn_reflns_number
 etc. will have to be added later.
 
 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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Mercury (MacRae et al., 2009)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'


_refine_special_details          'Refined as a 2-component twin.,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)+(0.0800P)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         3069
_refine_ls_number_parameters     227
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0876
_refine_ls_R_factor_gt           0.0758
_refine_ls_wR_factor_ref         0.2184
_refine_ls_wR_factor_gt          0.2154
_refine_ls_goodness_of_fit_ref   1.974
_refine_ls_restrained_S_all      1.974
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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 0.14052(6) 0.09169(4) 0.69439(5) 0.0392(3) Uani 1 1 d . . . . .
Br1 Br 0.1183(2) 0.11355(15) 0.90153(19) 0.0656(6) Uani 1 1 d . . . . .
N1 N 0.3011(12) -0.0311(8) 0.7459(12) 0.041(3) Uani 1 1 d . . . . .
C2 C 0.3622(18) -0.0617(12) 0.8625(17) 0.056(5) Uani 1 1 d . . . . .
H2 H 0.3424 -0.0365 0.9292 0.067 Uiso 1 1 calc R U . . .
C3 C 0.4527(17) -0.1290(13) 0.8844(16) 0.050(4) Uani 1 1 d . . . . .
H3 H 0.4960 -0.1478 0.9652 0.060 Uiso 1 1 calc R U . . .
C4 C 0.4784(18) -0.1683(11) 0.7849(18) 0.058(5) Uani 1 1 d . . . . .
H4 H 0.5381 -0.2148 0.7975 0.069 Uiso 1 1 calc R U . . .
C5 C 0.4141(16) -0.1377(10) 0.6659(16) 0.046(4) Uani 1 1 d . . . . .
H5 H 0.4309 -0.1629 0.5977 0.055 Uiso 1 1 calc R U . . .
C6 C 0.3244(14) -0.0691(10) 0.6495(14) 0.033(3) Uani 1 1 d . . . . .
C7 C 0.2493(13) -0.0331(8) 0.5242(13) 0.032(3) Uani 1 1 d . . . . .
C71 C 0.2743(13) -0.0689(10) 0.4128(14) 0.033(3) Uani 1 1 d . . . . .
C72 C 0.3261(19) -0.0149(12) 0.3403(18) 0.056(5) Uani 1 1 d . . . . .
H72 H 0.3403 0.0453 0.3596 0.067 Uiso 1 1 calc R U . . .
C73 C 0.356(2) -0.0492(15) 0.241(2) 0.068(6) Uani 1 1 d . . . . .
H73 H 0.3926 -0.0119 0.1955 0.082 Uiso 1 1 calc R U . . .
C74 C 0.3346(19) -0.1364(15) 0.2075(17) 0.062(5) Uani 1 1 d . . . . .
H74 H 0.3541 -0.1584 0.1389 0.075 Uiso 1 1 calc R U . . .
C75 C 0.2823(17) -0.1920(12) 0.2785(16) 0.051(4) Uani 1 1 d . . . . .
H75 H 0.2684 -0.2519 0.2580 0.061 Uiso 1 1 calc R U . . .
C76 C 0.2508(15) -0.1583(10) 0.3798(16) 0.045(4) Uani 1 1 d . . . . .
H76 H 0.2141 -0.1955 0.4253 0.054 Uiso 1 1 calc R U . . .
N8 N 0.1664(11) 0.0294(7) 0.5218(10) 0.033(3) Uani 1 1 d . . . . .
N9 N 0.0990(12) 0.0638(8) 0.4046(12) 0.036(3) Uani 1 1 d . . . . .
C10 C 0.0158(12) 0.1303(9) 0.4180(13) 0.027(3) Uani 1 1 d . . . . .
O10 O 0.0006(10) 0.1615(6) 0.5105(9) 0.041(3) Uani 1 1 d . . . . .
C11 C -0.0521(13) 0.1746(9) 0.2940(13) 0.030(3) Uani 1 1 d . . . . .
C12 C -0.1353(12) 0.2449(11) 0.2908(13) 0.035(4) Uani 1 1 d . . . . .
H12 H -0.1493 0.2610 0.3647 0.043 Uiso 1 1 calc R U . . .
N13 N -0.1976(11) 0.2918(8) 0.1877(10) 0.034(3) Uani 1 1 d . . . . .
C14 C -0.1738(15) 0.2681(12) 0.0826(14) 0.044(4) Uani 1 1 d . . . . .
H14 H -0.2119 0.3018 0.0114 0.053 Uiso 1 1 calc R U . . .
C15 C -0.0960(17) 0.1968(12) 0.0740(15) 0.053(5) Uani 1 1 d . . . . .
H15 H -0.0852 0.1816 -0.0016 0.064 Uiso 1 1 calc R U . . .
C16 C -0.0337(15) 0.1477(11) 0.1824(15) 0.043(4) Uani 1 1 d . . . . .
H16 H 0.0184 0.0989 0.1802 0.052 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Hg1 N8 2.267(12) . ?
Hg1 O10 2.392(9) . ?
Hg1 Br1 2.460(2) . ?
Hg1 N1 2.470(12) . ?
Hg1 N13 2.491(12) 4_666 ?
N1 C6 1.33(2) . ?
N1 C2 1.36(2) . ?
C2 C3 1.37(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.38(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.38(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.38(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.50(2) . ?
C7 N8 1.291(17) . ?
C7 C71 1.48(2) . ?
C71 C72 1.39(2) . ?
C71 C76 1.40(2) . ?
C72 C73 1.37(3) . ?
C72 H72 0.9300 . ?
C73 C74 1.36(3) . ?
C73 H73 0.9300 . ?
C74 C75 1.40(3) . ?
C74 H74 0.9300 . ?
C75 C76 1.39(2) . ?
C75 H75 0.9300 . ?
C76 H76 0.9300 . ?
N8 N9 1.395(16) . ?
N9 C10 1.383(18) . ?
C10 O10 1.208(16) . ?
C10 C11 1.516(19) . ?
C11 C12 1.38(2) . ?
C11 C16 1.40(2) . ?
C12 N13 1.348(17) . ?
C12 H12 0.9300 . ?
N13 C14 1.346(19) . ?
N13 Hg1 2.491(12) 4_565 ?
C14 C15 1.38(2) . ?
C14 H14 0.9300 . ?
C15 C16 1.41(2) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N8 Hg1 O10 69.2(4) . . ?
N8 Hg1 Br1 163.2(3) . . ?
O10 Hg1 Br1 123.2(3) . . ?
N8 Hg1 N1 68.0(4) . . ?
O10 Hg1 N1 137.2(4) . . ?
Br1 Hg1 N1 98.6(3) . . ?
N8 Hg1 N13 88.9(4) . 4_666 ?
O10 Hg1 N13 85.4(4) . 4_666 ?
Br1 Hg1 N13 102.7(3) . 4_666 ?
N1 Hg1 N13 94.9(4) . 4_666 ?
C6 N1 C2 119.8(14) . . ?
C6 N1 Hg1 115.4(9) . . ?
C2 N1 Hg1 124.7(12) . . ?
N1 C2 C3 121.5(18) . . ?
N1 C2 H2 119.2 . . ?
C3 C2 H2 119.2 . . ?
C2 C3 C4 119.1(15) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 H3 120.5 . . ?
C3 C4 C5 119.1(16) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C4 C5 C6 119.3(17) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
N1 C6 C5 121.2(14) . . ?
N1 C6 C7 116.1(13) . . ?
C5 C6 C7 122.7(14) . . ?
N8 C7 C71 124.2(12) . . ?
N8 C7 C6 116.4(13) . . ?
C71 C7 C6 119.3(12) . . ?
C72 C71 C76 118.3(15) . . ?
C72 C71 C7 120.7(14) . . ?
C76 C71 C7 120.9(14) . . ?
C73 C72 C71 120.9(16) . . ?
C73 C72 H72 119.6 . . ?
C71 C72 H72 119.6 . . ?
C74 C73 C72 121.8(19) . . ?
C74 C73 H73 119.1 . . ?
C72 C73 H73 119.1 . . ?
C73 C74 C75 118.5(17) . . ?
C73 C74 H74 120.8 . . ?
C75 C74 H74 120.8 . . ?
C76 C75 C74 120.6(17) . . ?
C76 C75 H75 119.7 . . ?
C74 C75 H75 119.7 . . ?
C75 C76 C71 119.9(16) . . ?
C75 C76 H76 120.1 . . ?
C71 C76 H76 120.1 . . ?
C7 N8 N9 115.9(12) . . ?
C7 N8 Hg1 123.9(9) . . ?
N9 N8 Hg1 120.0(8) . . ?
C10 N9 N8 108.8(11) . . ?
O10 C10 N9 130.5(12) . . ?
O10 C10 C11 118.4(12) . . ?
N9 C10 C11 110.7(12) . . ?
C10 O10 Hg1 111.4(8) . . ?
C12 C11 C16 118.4(13) . . ?
C12 C11 C10 118.5(13) . . ?
C16 C11 C10 123.0(12) . . ?
N13 C12 C11 124.3(14) . . ?
N13 C12 H12 117.9 . . ?
C11 C12 H12 117.9 . . ?
C14 N13 C12 116.6(12) . . ?
C14 N13 Hg1 123.2(9) . 4_565 ?
C12 N13 Hg1 120.1(10) . 4_565 ?
N13 C14 C15 124.0(14) . . ?
N13 C14 H14 118.0 . . ?
C15 C14 H14 118.0 . . ?
C14 C15 C16 118.4(16) . . ?
C14 C15 H15 120.8 . . ?
C16 C15 H15 120.8 . . ?
C11 C16 C15 118.2(14) . . ?
C11 C16 H16 120.9 . . ?
C15 C16 H16 120.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 N1 C2 C3 3(3) . . . . ?
Hg1 N1 C2 C3 -178.5(14) . . . . ?
N1 C2 C3 C4 -2(3) . . . . ?
C2 C3 C4 C5 1(3) . . . . ?
C3 C4 C5 C6 -1(3) . . . . ?
C2 N1 C6 C5 -2(2) . . . . ?
Hg1 N1 C6 C5 178.9(12) . . . . ?
C2 N1 C6 C7 178.0(14) . . . . ?
Hg1 N1 C6 C7 -0.7(16) . . . . ?
C4 C5 C6 N1 1(2) . . . . ?
C4 C5 C6 C7 -179.0(15) . . . . ?
N1 C6 C7 N8 -2.1(19) . . . . ?
C5 C6 C7 N8 178.3(14) . . . . ?
N1 C6 C7 C71 177.1(13) . . . . ?
C5 C6 C7 C71 -2(2) . . . . ?
N8 C7 C71 C72 64(2) . . . . ?
C6 C7 C71 C72 -115.6(16) . . . . ?
N8 C7 C71 C76 -118.5(16) . . . . ?
C6 C7 C71 C76 62.3(18) . . . . ?
C76 C71 C72 C73 -2(3) . . . . ?
C7 C71 C72 C73 176.3(17) . . . . ?
C71 C72 C73 C74 1(3) . . . . ?
C72 C73 C74 C75 -1(3) . . . . ?
C73 C74 C75 C76 1(3) . . . . ?
C74 C75 C76 C71 -2(2) . . . . ?
C72 C71 C76 C75 2(2) . . . . ?
C7 C71 C76 C75 -176.3(14) . . . . ?
C71 C7 N8 N9 -1(2) . . . . ?
C6 C7 N8 N9 178.7(12) . . . . ?
C71 C7 N8 Hg1 -174.8(10) . . . . ?
C6 C7 N8 Hg1 4.3(17) . . . . ?
C7 N8 N9 C10 -179.3(12) . . . . ?
Hg1 N8 N9 C10 -4.8(15) . . . . ?
N8 N9 C10 O10 3(2) . . . . ?
N8 N9 C10 C11 175.7(11) . . . . ?
N9 C10 O10 Hg1 0(2) . . . . ?
C11 C10 O10 Hg1 -172.2(9) . . . . ?
O10 C10 C11 C12 -4(2) . . . . ?
N9 C10 C11 C12 -177.6(13) . . . . ?
O10 C10 C11 C16 175.3(14) . . . . ?
N9 C10 C11 C16 2.0(19) . . . . ?
C16 C11 C12 N13 -2(2) . . . . ?
C10 C11 C12 N13 177.5(12) . . . . ?
C11 C12 N13 C14 -1(2) . . . . ?
C11 C12 N13 Hg1 174.7(11) . . . 4_565 ?
C12 N13 C14 C15 4(2) . . . . ?
Hg1 N13 C14 C15 -172.1(13) 4_565 . . . ?
N13 C14 C15 C16 -3(3) . . . . ?
C12 C11 C16 C15 3(2) . . . . ?
C10 C11 C16 C15 -176.5(14) . . . . ?
C14 C15 C16 C11 -1(2) . . . . ?

_refine_diff_density_max         3.133
_refine_diff_density_min         -3.438
_refine_diff_density_rms         0.496

####################################################################### 
# 
# 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_5
_database_code_depnum_ccdc_archive 'CCDC 1583985'
_audit_update_record             
;
2017-11-06 deposited with the CCDC.
2018-01-09 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H13 Hg I N4 O'
_chemical_formula_sum            'C18 H13 Hg I N4 O'
_chemical_formula_weight         628.81

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   10.7093(10)
_cell_length_b                   15.1214(14)
_cell_length_c                   11.4424(11)
_cell_angle_alpha                90
_cell_angle_beta                 110.2750(10)
_cell_angle_gamma                90
_cell_volume                     1738.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    3757
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      28.24

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.403
_exptl_crystal_F_000             1160
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    10.645
_shelx_estimated_absorpt_T_min   0.265
_shelx_estimated_absorpt_T_max   0.815
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4616
_exptl_absorpt_correction_T_max  0.8153
_exptl_absorpt_process_details   'Bruker SAINT (Bruker-AXS 2009)'
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      100(1)
_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  'Bruker Smart APEX CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_number            7894
_diffrn_reflns_av_unetI/netI     0.0486
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.246
_diffrn_reflns_theta_max         28.312
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             7894
_reflns_number_gt                6656
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _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 APEX2 (Bruker-AXS, 2010)'
_computing_cell_refinement       'Bruker SAINT (Bruker-AXS 2009)'
_computing_data_reduction        'Bruker SAINT (Bruker-AXS 2009)'
_computing_structure_solution    'SHELXT-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Mercury (MacRae et al., 2009)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'

_refine_special_details          'Refined as a 2-component twin.,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)+(0.0258P)²+7.3630P] 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         7894
_refine_ls_number_parameters     227
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0491
_refine_ls_R_factor_gt           0.0365
_refine_ls_wR_factor_ref         0.0799
_refine_ls_wR_factor_gt          0.0749
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.002
_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 0.36066(2) 0.58686(2) 0.30383(2) 0.01198(7) Uani 1 1 d . . . . .
I1 I 0.38339(5) 0.60190(3) 0.08334(4) 0.01837(11) Uani 1 1 d . . . . .
N1 N 0.1959(5) 0.4649(3) 0.2534(5) 0.0135(11) Uani 1 1 d . . . . .
C2 C 0.1321(7) 0.4332(4) 0.1391(6) 0.0161(14) Uani 1 1 d . . . . .
H2 H 0.1483 0.4593 0.0702 0.019 Uiso 1 1 calc R U . . .
C3 C 0.0434(7) 0.3635(5) 0.1180(6) 0.0177(14) Uani 1 1 d . . . . .
H3 H -0.0002 0.3418 0.0360 0.021 Uiso 1 1 calc R U . . .
C4 C 0.0193(7) 0.3262(4) 0.2181(6) 0.0174(14) Uani 1 1 d . . . . .
H4 H -0.0407 0.2780 0.2061 0.021 Uiso 1 1 calc R U . . .
C5 C 0.0837(7) 0.3599(4) 0.3364(7) 0.0156(13) Uani 1 1 d . . . . .
H5 H 0.0668 0.3359 0.4061 0.019 Uiso 1 1 calc R U . . .
C6 C 0.1732(6) 0.4293(4) 0.3521(6) 0.0110(12) Uani 1 1 d . . . . .
C7 C 0.2502(6) 0.4669(4) 0.4764(6) 0.0117(12) Uani 1 1 d . . . . .
C71 C 0.2258(6) 0.4331(4) 0.5885(6) 0.0134(13) Uani 1 1 d . . . . .
C72 C 0.1765(7) 0.4898(4) 0.6589(6) 0.0172(14) Uani 1 1 d . . . . .
H72 H 0.1635 0.5507 0.6377 0.021 Uiso 1 1 calc R U . . .
C73 C 0.1464(7) 0.4572(5) 0.7601(7) 0.0222(15) Uani 1 1 d . . . . .
H73 H 0.1133 0.4960 0.8078 0.027 Uiso 1 1 calc R U . . .
C74 C 0.1646(7) 0.3687(5) 0.7910(7) 0.0208(15) Uani 1 1 d . . . . .
H74 H 0.1417 0.3464 0.8585 0.025 Uiso 1 1 calc R U . . .
C75 C 0.2163(7) 0.3123(5) 0.7237(7) 0.0185(14) Uani 1 1 d . . . . .
H75 H 0.2317 0.2519 0.7471 0.022 Uiso 1 1 calc R U . . .
C76 C 0.2457(6) 0.3442(4) 0.6217(6) 0.0143(13) Uani 1 1 d . . . . .
H76 H 0.2795 0.3051 0.5748 0.017 Uiso 1 1 calc R U . . .
N8 N 0.3355(5) 0.5292(3) 0.4806(5) 0.0102(10) Uani 1 1 d . . . . .
N9 N 0.4070(5) 0.5646(3) 0.5944(5) 0.0118(11) Uani 1 1 d . . . . .
C10 C 0.4867(6) 0.6308(4) 0.5824(5) 0.0063(11) Uani 1 1 d . U . . .
O10 O 0.5049(4) 0.6584(3) 0.4875(4) 0.0121(9) Uani 1 1 d . . . . .
C11 C 0.5571(6) 0.6761(4) 0.7051(6) 0.0117(13) Uani 1 1 d . . . . .
C12 C 0.6413(6) 0.7470(4) 0.7060(6) 0.0104(12) Uani 1 1 d . . . . .
H12 H 0.6557 0.7617 0.6310 0.013 Uiso 1 1 calc R U . . .
N13 N 0.7028(5) 0.7953(4) 0.8089(5) 0.0145(11) Uani 1 1 d . . . . .
C14 C 0.6783(6) 0.7721(4) 0.9122(6) 0.0133(13) Uani 1 1 d . . . . .
H14 H 0.7174 0.8074 0.9844 0.016 Uiso 1 1 calc R U . . .
C15 C 0.6025(7) 0.7028(5) 0.9222(6) 0.0180(14) Uani 1 1 d . . . . .
H15 H 0.5936 0.6882 0.9997 0.022 Uiso 1 1 calc R U . . .
C16 C 0.5384(6) 0.6537(4) 0.8160(6) 0.0130(13) Uani 1 1 d . . . . .
H16 H 0.4826 0.6055 0.8187 0.016 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Hg1 N8 2.303(5) . ?
Hg1 O10 2.393(4) . ?
Hg1 N13 2.471(5) 4_575 ?
Hg1 N1 2.478(5) . ?
Hg1 I1 2.6272(5) . ?
N1 C2 1.338(8) . ?
N1 C6 1.347(8) . ?
C2 C3 1.383(9) . ?
C2 H2 0.9500 . ?
C3 C4 1.379(10) . ?
C3 H3 0.9500 . ?
C4 C5 1.386(9) . ?
C4 H4 0.9500 . ?
C5 C6 1.390(9) . ?
C5 H5 0.9500 . ?
C6 C7 1.488(9) . ?
C7 N8 1.302(8) . ?
C7 C71 1.485(9) . ?
C71 C76 1.394(9) . ?
C71 C72 1.398(9) . ?
C72 C73 1.395(10) . ?
C72 H72 0.9500 . ?
C73 C74 1.381(11) . ?
C73 H73 0.9500 . ?
C74 C75 1.385(10) . ?
C74 H74 0.9500 . ?
C75 C76 1.396(9) . ?
C75 H75 0.9500 . ?
C76 H76 0.9500 . ?
N8 N9 1.369(7) . ?
N9 C10 1.353(8) . ?
C10 O10 1.240(7) . ?
C10 C11 1.509(8) . ?
C11 C16 1.393(9) . ?
C11 C12 1.398(8) . ?
C12 N13 1.347(8) . ?
C12 H12 0.9500 . ?
N13 C14 1.343(8) . ?
N13 Hg1 2.471(5) 4_676 ?
C14 C15 1.355(9) . ?
C14 H14 0.9500 . ?
C15 C16 1.386(9) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?

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
N8 Hg1 O10 68.65(17) . . ?
N8 Hg1 N13 87.89(18) . 4_575 ?
O10 Hg1 N13 83.78(16) . 4_575 ?
N8 Hg1 N1 68.42(18) . . ?
O10 Hg1 N1 137.05(16) . . ?
N13 Hg1 N1 96.01(18) 4_575 . ?
N8 Hg1 I1 162.64(13) . . ?
O10 Hg1 I1 123.92(11) . . ?
N13 Hg1 I1 104.59(12) 4_575 . ?
N1 Hg1 I1 97.84(12) . . ?
C2 N1 C6 119.8(6) . . ?
C2 N1 Hg1 125.1(4) . . ?
C6 N1 Hg1 115.0(4) . . ?
N1 C2 C3 122.1(6) . . ?
N1 C2 H2 119.0 . . ?
C3 C2 H2 119.0 . . ?
C4 C3 C2 118.8(6) . . ?
C4 C3 H3 120.6 . . ?
C2 C3 H3 120.6 . . ?
C3 C4 C5 119.2(6) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C4 C5 C6 119.5(6) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
N1 C6 C5 120.7(6) . . ?
N1 C6 C7 116.6(5) . . ?
C5 C6 C7 122.7(6) . . ?
N8 C7 C71 123.3(6) . . ?
N8 C7 C6 117.4(6) . . ?
C71 C7 C6 119.3(5) . . ?
C76 C71 C72 119.1(6) . . ?
C76 C71 C7 120.7(6) . . ?
C72 C71 C7 120.1(6) . . ?
C73 C72 C71 120.2(6) . . ?
C73 C72 H72 119.9 . . ?
C71 C72 H72 119.9 . . ?
C74 C73 C72 120.1(7) . . ?
C74 C73 H73 119.9 . . ?
C72 C73 H73 119.9 . . ?
C73 C74 C75 120.2(7) . . ?
C73 C74 H74 119.9 . . ?
C75 C74 H74 119.9 . . ?
C74 C75 C76 120.1(7) . . ?
C74 C75 H75 120.0 . . ?
C76 C75 H75 120.0 . . ?
C71 C76 C75 120.3(6) . . ?
C71 C76 H76 119.9 . . ?
C75 C76 H76 119.9 . . ?
C7 N8 N9 118.1(5) . . ?
C7 N8 Hg1 122.4(4) . . ?
N9 N8 Hg1 119.4(4) . . ?
C10 N9 N8 110.9(5) . . ?
O10 C10 N9 129.4(5) . . ?
O10 C10 C11 118.8(5) . . ?
N9 C10 C11 111.8(5) . . ?
C10 O10 Hg1 111.5(4) . . ?
C16 C11 C12 118.4(6) . . ?
C16 C11 C10 123.6(5) . . ?
C12 C11 C10 118.0(5) . . ?
N13 C12 C11 122.7(6) . . ?
N13 C12 H12 118.6 . . ?
C11 C12 H12 118.6 . . ?
C14 N13 C12 116.2(5) . . ?
C14 N13 Hg1 123.6(4) . 4_676 ?
C12 N13 Hg1 120.1(4) . 4_676 ?
N13 C14 C15 125.6(6) . . ?
N13 C14 H14 117.2 . . ?
C15 C14 H14 117.2 . . ?
C14 C15 C16 118.0(6) . . ?
C14 C15 H15 121.0 . . ?
C16 C15 H15 121.0 . . ?
C15 C16 C11 119.0(6) . . ?
C15 C16 H16 120.5 . . ?
C11 C16 H16 120.5 . . ?

_refine_diff_density_max         2.345
_refine_diff_density_min         -1.311
_refine_diff_density_rms         0.233

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_4
_database_code_depnum_ccdc_archive 'CCDC 1583984'
_audit_update_record             
;
2017-11-06 deposited with the CCDC.
2018-01-09 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         'C18 H14 Hg I2 N4 O, C H4 O'
_chemical_formula_sum            'C19 H18 Hg I2 N4 O2'
_chemical_formula_weight         788.76

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'
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'
O O 0.0106 0.0060 '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                   9.9325(18)
_cell_length_b                   10.233(2)
_cell_length_c                   12.755(3)
_cell_angle_alpha                91.65(2)
_cell_angle_beta                 110.98(2)
_cell_angle_gamma                106.46(2)
_cell_volume                     1148.5(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    1274
_cell_measurement_theta_min      3
_cell_measurement_theta_max      22

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.281
_exptl_crystal_F_000             724
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    9.409
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.42
_exptl_absorpt_correction_T_max  0.85
_exptl_absorpt_process_details   'SADABS, Bruker-AXS, 2010'
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      295(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_number            7502
_diffrn_reflns_av_unetI/netI     0.1857
_diffrn_reflns_av_R_equivalents  0.1292
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.098
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.941
_diffrn_measured_fraction_theta_full 0.941
_diffrn_reflns_Laue_measured_fraction_max 0.941
_diffrn_reflns_Laue_measured_fraction_full 0.941
_diffrn_reflns_point_group_measured_fraction_max 0.941
_diffrn_reflns_point_group_measured_fraction_full 0.941
_reflns_number_total             3802
_reflns_number_gt                1774
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Mercury (MacRae et al., 2009)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'

_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)+(0.0600P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0060(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3802
_refine_ls_number_parameters     253
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1182
_refine_ls_R_factor_gt           0.0622
_refine_ls_wR_factor_ref         0.1577
_refine_ls_wR_factor_gt          0.1458
_refine_ls_goodness_of_fit_ref   0.825
_refine_ls_restrained_S_all      0.824
_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 0.15146(9) -0.05801(7) 0.19197(7) 0.0616(3) Uani 1 1 d . . . . .
I1 I -0.04280(15) -0.24748(13) 0.24714(12) 0.0703(4) Uani 1 1 d . . . . .
I2 I 0.21752(16) 0.16044(12) 0.09153(10) 0.0685(4) Uani 1 1 d . . . . .
N1 N 0.278(2) -0.2038(15) 0.1278(13) 0.066(4) Uani 1 1 d . . . . .
C2 C 0.203(3) -0.316(2) 0.0547(16) 0.072(6) Uani 1 1 d . . . . .
H2 H 0.0976 -0.3431 0.0269 0.086 Uiso 1 1 calc R U . . .
C3 C 0.270(3) -0.400(2) 0.015(3) 0.113(10) Uani 1 1 d . . . . .
H3 H 0.2137 -0.4825 -0.0344 0.135 Uiso 1 1 calc R U . . .
C4 C 0.431(4) -0.348(3) 0.055(3) 0.128(11) Uani 1 1 d . . . . .
H4 H 0.4820 -0.3945 0.0271 0.154 Uiso 1 1 calc R U . . .
C5 C 0.510(3) -0.239(2) 0.130(2) 0.091(8) Uani 1 1 d . . . . .
H5 H 0.6152 -0.2131 0.1599 0.109 Uiso 1 1 calc R U . . .
C6 C 0.435(2) -0.1614(16) 0.1639(14) 0.053(5) Uani 1 1 d . . . . .
C7 C 0.518(3) -0.0372(19) 0.2484(17) 0.070(6) Uani 1 1 d . . . . .
C71 C 0.685(2) 0.0364(15) 0.2694(15) 0.049(4) Uani 1 1 d . . . . .
C72 C 0.795(2) 0.0608(19) 0.3745(15) 0.058(5) Uani 1 1 d . . . . .
H72 H 0.7699 0.0357 0.4363 0.070 Uiso 1 1 calc R U . . .
C73 C 0.948(2) 0.124(2) 0.3896(17) 0.070(6) Uani 1 1 d . . . . .
H73 H 1.0246 0.1356 0.4605 0.084 Uiso 1 1 calc R U . . .
C74 C 0.981(2) 0.1680(17) 0.302(2) 0.072(6) Uani 1 1 d . . . . .
H74 H 1.0808 0.2167 0.3139 0.086 Uiso 1 1 calc R U . . .
C75 C 0.865(2) 0.141(2) 0.1907(19) 0.080(6) Uani 1 1 d . . . . .
H75 H 0.8867 0.1698 0.1282 0.096 Uiso 1 1 calc R U . . .
C76 C 0.719(3) 0.070(2) 0.1819(18) 0.075(6) Uani 1 1 d . . . . .
H76 H 0.6419 0.0450 0.1101 0.090 Uiso 1 1 calc R U . . .
N8 N 0.4454(16) -0.0028(13) 0.3053(12) 0.047(3) Uani 1 1 d . . . . .
N9 N 0.5148(16) 0.1147(14) 0.3876(12) 0.053(4) Uani 1 1 d . . . . .
H9 H 0.6078 0.1641 0.4051 0.064 Uiso 1 1 calc R U . . .
C10 C 0.427(2) 0.1453(16) 0.4373(12) 0.045(4) Uani 1 1 d . . . . .
O10 O 0.2936(14) 0.0747(12) 0.4128(10) 0.060(3) Uani 1 1 d . . . . .
C11 C 0.4964(18) 0.2658(14) 0.5215(13) 0.042(4) Uani 1 1 d . . . . .
C12 C 0.407(3) 0.336(2) 0.5473(15) 0.065(5) Uani 1 1 d . . . . .
H12 H 0.3024 0.3031 0.5070 0.078 Uiso 1 1 calc R U . . .
N13 N 0.464(3) 0.4467(17) 0.6271(16) 0.083(6) Uani 1 1 d . . . . .
C14 C 0.615(3) 0.490(2) 0.6834(18) 0.080(7) Uani 1 1 d . . . . .
H14 H 0.6563 0.5693 0.7364 0.096 Uiso 1 1 calc R U . . .
C15 C 0.713(3) 0.426(2) 0.6691(17) 0.081(7) Uani 1 1 d . . . . .
H15 H 0.8166 0.4598 0.7127 0.098 Uiso 1 1 calc R U . . .
C16 C 0.655(2) 0.3115(17) 0.5892(14) 0.059(5) Uani 1 1 d . . . . .
H16 H 0.7175 0.2642 0.5793 0.070 Uiso 1 1 calc R U . . .
O1A O 0.6978(18) 0.3705(13) 0.3634(12) 0.086(4) Uani 1 1 d D . . . .
H1A H 0.6688 0.4309 0.3869 0.103 Uiso 1 1 d R U . A .
C1A C 0.857(3) 0.450(6) 0.405(5) 0.14(2) Uiso 0.5 1 d D . P A 1
H1A1 H 0.8688 0.5464 0.4088 0.204 Uiso 0.5 1 d R U P A 1
H1A2 H 0.9025 0.4254 0.3555 0.204 Uiso 0.5 1 d R U P A 1
H1A3 H 0.9061 0.4295 0.4795 0.204 Uiso 0.5 1 d R U P A 1
C1A' C 0.694(7) 0.398(6) 0.252(2) 0.115(17) Uiso 0.5 1 d D . P A 2
H1A4 H 0.5924 0.3697 0.1961 0.172 Uiso 0.5 1 d R U P A 2
H1A5 H 0.7520 0.3481 0.2317 0.172 Uiso 0.5 1 d R U P A 2
H1A6 H 0.7405 0.4949 0.2555 0.172 Uiso 0.5 1 d R 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 N1 2.489(16) . ?
Hg1 I1 2.6283(16) . ?
Hg1 N8 2.632(14) . ?
Hg1 I2 2.6466(15) . ?
N1 C2 1.31(2) . ?
N1 C6 1.39(2) . ?
C2 C3 1.41(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.42(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.29(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.39(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.47(3) . ?
C7 N8 1.29(2) . ?
C7 C71 1.53(3) . ?
C71 C76 1.31(2) . ?
C71 C72 1.35(2) . ?
C72 C73 1.41(3) . ?
C72 H72 0.9300 . ?
C73 C74 1.32(3) . ?
C73 H73 0.9300 . ?
C74 C75 1.43(3) . ?
C74 H74 0.9300 . ?
C75 C76 1.39(3) . ?
C75 H75 0.9300 . ?
C76 H76 0.9300 . ?
N8 N9 1.400(19) . ?
N9 C10 1.34(2) . ?
N9 H9 0.8600 . ?
C10 O10 1.23(2) . ?
C10 C11 1.44(2) . ?
C11 C12 1.40(2) . ?
C11 C16 1.42(2) . ?
C12 N13 1.34(3) . ?
C12 H12 0.9300 . ?
N13 C14 1.34(3) . ?
C14 C15 1.38(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.37(3) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
O1A C1A 1.446(10) . ?
O1A C1A' 1.446(10) . ?
O1A H1A 0.8402 . ?
C1A H1A1 0.9600 . ?
C1A H1A2 0.9600 . ?
C1A H1A3 0.9600 . ?
C1A' H1A4 0.9600 . ?
C1A' H1A5 0.9600 . ?
C1A' H1A6 0.9600 . ?

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 Hg1 I1 99.9(4) . . ?
N1 Hg1 N8 63.2(5) . . ?
I1 Hg1 N8 120.1(3) . . ?
N1 Hg1 I2 100.6(4) . . ?
I1 Hg1 I2 151.04(6) . . ?
N8 Hg1 I2 87.5(3) . . ?
C2 N1 C6 116.7(17) . . ?
C2 N1 Hg1 123.3(15) . . ?
C6 N1 Hg1 119.8(11) . . ?
N1 C2 C3 125(2) . . ?
N1 C2 H2 117.5 . . ?
C3 C2 H2 117.5 . . ?
C2 C3 C4 114(2) . . ?
C2 C3 H3 122.9 . . ?
C4 C3 H3 122.9 . . ?
C5 C4 C3 123(2) . . ?
C5 C4 H4 118.7 . . ?
C3 C4 H4 118.7 . . ?
C4 C5 C6 119(2) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C5 C6 N1 121.7(18) . . ?
C5 C6 C7 122(2) . . ?
N1 C6 C7 116.5(17) . . ?
N8 C7 C6 116.2(19) . . ?
N8 C7 C71 124.6(18) . . ?
C6 C7 C71 119.0(18) . . ?
C76 C71 C72 121(2) . . ?
C76 C71 C7 118.0(18) . . ?
C72 C71 C7 121.3(16) . . ?
C71 C72 C73 119.5(17) . . ?
C71 C72 H72 120.2 . . ?
C73 C72 H72 120.2 . . ?
C74 C73 C72 119.7(19) . . ?
C74 C73 H73 120.1 . . ?
C72 C73 H73 120.1 . . ?
C73 C74 C75 121(2) . . ?
C73 C74 H74 119.6 . . ?
C75 C74 H74 119.6 . . ?
C76 C75 C74 115.6(19) . . ?
C76 C75 H75 122.2 . . ?
C74 C75 H75 122.2 . . ?
C71 C76 C75 123(2) . . ?
C71 C76 H76 118.4 . . ?
C75 C76 H76 118.4 . . ?
C7 N8 N9 120.6(16) . . ?
C7 N8 Hg1 115.1(13) . . ?
N9 N8 Hg1 115.4(9) . . ?
C10 N9 N8 115.8(13) . . ?
C10 N9 H9 122.1 . . ?
N8 N9 H9 122.1 . . ?
O10 C10 N9 122.5(15) . . ?
O10 C10 C11 121.2(17) . . ?
N9 C10 C11 116.3(16) . . ?
C12 C11 C16 117.2(15) . . ?
C12 C11 C10 120.4(17) . . ?
C16 C11 C10 122.1(15) . . ?
N13 C12 C11 123.5(19) . . ?
N13 C12 H12 118.2 . . ?
C11 C12 H12 118.2 . . ?
C14 N13 C12 116(2) . . ?
N13 C14 C15 125(2) . . ?
N13 C14 H14 117.5 . . ?
C15 C14 H14 117.5 . . ?
C16 C15 C14 118(2) . . ?
C16 C15 H15 120.8 . . ?
C14 C15 H15 120.8 . . ?
C15 C16 C11 119.1(19) . . ?
C15 C16 H16 120.5 . . ?
C11 C16 H16 120.5 . . ?
C1A O1A H1A 96.5 . . ?
C1A' O1A H1A 105.8 . . ?
O1A C1A H1A1 110.1 . . ?
O1A C1A H1A2 110.0 . . ?
H1A1 C1A H1A2 109.5 . . ?
O1A C1A H1A3 108.3 . . ?
H1A1 C1A H1A3 109.5 . . ?
H1A2 C1A H1A3 109.5 . . ?
O1A C1A' H1A4 111.8 . . ?
O1A C1A' H1A5 107.8 . . ?
H1A4 C1A' H1A5 109.5 . . ?
O1A C1A' H1A6 108.8 . . ?
H1A4 C1A' H1A6 109.5 . . ?
H1A5 C1A' H1A6 109.5 . . ?

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
C6 N1 C2 C3 3(3) . . . . ?
Hg1 N1 C2 C3 178.7(19) . . . . ?
N1 C2 C3 C4 -4(4) . . . . ?
C2 C3 C4 C5 5(5) . . . . ?
C3 C4 C5 C6 -6(5) . . . . ?
C4 C5 C6 N1 6(4) . . . . ?
C4 C5 C6 C7 180(2) . . . . ?
C2 N1 C6 C5 -4(3) . . . . ?
Hg1 N1 C6 C5 -179.6(15) . . . . ?
C2 N1 C6 C7 -178.4(16) . . . . ?
Hg1 N1 C6 C7 5.9(19) . . . . ?
C5 C6 C7 N8 -154.7(19) . . . . ?
N1 C6 C7 N8 20(2) . . . . ?
C5 C6 C7 C71 21(3) . . . . ?
N1 C6 C7 C71 -164.4(15) . . . . ?
N8 C7 C71 C76 -132(2) . . . . ?
C6 C7 C71 C76 53(2) . . . . ?
N8 C7 C71 C72 51(3) . . . . ?
C6 C7 C71 C72 -124.4(19) . . . . ?
C76 C71 C72 C73 1(3) . . . . ?
C7 C71 C72 C73 177.8(17) . . . . ?
C71 C72 C73 C74 5(3) . . . . ?
C72 C73 C74 C75 -5(3) . . . . ?
C73 C74 C75 C76 1(3) . . . . ?
C72 C71 C76 C75 -5(3) . . . . ?
C7 C71 C76 C75 177.5(19) . . . . ?
C74 C75 C76 C71 4(3) . . . . ?
C6 C7 N8 N9 -179.7(14) . . . . ?
C71 C7 N8 N9 5(2) . . . . ?
C6 C7 N8 Hg1 -33.9(18) . . . . ?
C71 C7 N8 Hg1 150.6(13) . . . . ?
C7 N8 N9 C10 176.5(15) . . . . ?
Hg1 N8 N9 C10 30.8(16) . . . . ?
N8 N9 C10 O10 0(2) . . . . ?
N8 N9 C10 C11 -179.7(13) . . . . ?
O10 C10 C11 C12 -24(2) . . . . ?
N9 C10 C11 C12 156.2(16) . . . . ?
O10 C10 C11 C16 150.0(16) . . . . ?
N9 C10 C11 C16 -30(2) . . . . ?
C16 C11 C12 N13 4(3) . . . . ?
C10 C11 C12 N13 178.2(16) . . . . ?
C11 C12 N13 C14 0(3) . . . . ?
C12 N13 C14 C15 -3(3) . . . . ?
N13 C14 C15 C16 2(3) . . . . ?
C14 C15 C16 C11 2(3) . . . . ?
C12 C11 C16 C15 -5(2) . . . . ?
C10 C11 C16 C15 -179.0(17) . . . . ?

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
C5 H5 I1 0.93 3.30 4.18(2) 158.3 1_655
C14 H14 I2 0.93 3.12 4.05(2) 177.3 2_666
N9 H9 O1A 0.86 2.21 2.829(18) 128.9 .
O1A H1A N13 0.84 2.03 2.81(2) 155.2 2_666

_refine_diff_density_max         1.285
_refine_diff_density_min         -2.245
_refine_diff_density_rms         0.258

