# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_6
_database_code_depnum_ccdc_archive 'CCDC 1506192'
_audit_update_record             
;
2016-09-24 deposited with the CCDC.
2016-10-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H14 Hg I2 N4 O2'
_chemical_formula_weight         712.67

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           1
_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'

_cell_length_a                   7.6855(15)
_cell_length_b                   7.8344(16)
_cell_length_c                   8.1579(16)
_cell_angle_alpha                91.15(3)
_cell_angle_beta                 104.78(3)
_cell_angle_gamma                116.81(3)
_cell_volume                     418.66(18)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5874
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      24.86

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.827
_exptl_crystal_F_000             322
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    12.889
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2438
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'phi and omega scans'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7105
_diffrn_reflns_av_unetI/netI     0.0316
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       ?
_diffrn_reflns_limit_h_max       ?
_diffrn_reflns_limit_k_min       ?
_diffrn_reflns_limit_k_max       ?
_diffrn_reflns_limit_l_min       ?
_diffrn_reflns_limit_l_max       ?
_diffrn_reflns_theta_min         3.419
_diffrn_reflns_theta_max         36.252
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.943
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.943
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.943
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             7105
_reflns_number_gt                6624
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         1.000
_reflns_Friedel_fraction_max     0.943
_reflns_Friedel_fraction_full    0.997

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_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)+(0.0419P)²+0.8318P] 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
_refine_ls_extinction_coef       0.0057(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.463(5)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         7105
_refine_ls_number_parameters     202
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0368
_refine_ls_R_factor_gt           0.0323
_refine_ls_wR_factor_ref         0.0814
_refine_ls_wR_factor_gt          0.0788
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_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 0.50000(2) 0.50000(2) 0.50000(2) 0.03042(9) Uani 1 1 d . . . . .
C1 C 0.7018(14) 0.5016(12) 0.9219(11) 0.0321(15) Uani 1 1 d . . . . .
H1 H 0.5671 0.3995 0.9031 0.039 Uiso 1 1 calc R U . . .
C2 C 0.8406(14) 0.5425(12) 1.0824(11) 0.0320(15) Uani 1 1 d . . . . .
H2 H 0.8032 0.4689 1.1704 0.038 Uiso 1 1 calc R U . . .
C3 C 1.0340(15) 0.6932(14) 1.1104(10) 0.0355(17) Uani 1 1 d . . . . .
H3 H 1.1331 0.7260 1.2191 0.043 Uiso 1 1 calc R U . . .
C4 C 1.0837(12) 0.7973(12) 0.9780(9) 0.0289(14) Uani 1 1 d . . . . .
H4 H 1.2167 0.9020 0.9953 0.035 Uiso 1 1 calc R U . . .
C5 C 0.9338(11) 0.7450(10) 0.8185(8) 0.0224(11) Uani 1 1 d . . . . .
C6 C 0.9751(11) 0.8545(10) 0.6746(8) 0.0219(11) Uani 1 1 d . . . . .
C7 C 0.6986(12) 0.8362(12) 0.2512(9) 0.0266(12) Uani 1 1 d . . . . .
C8 C 0.7595(12) 0.9599(11) 0.1175(9) 0.0241(12) Uani 1 1 d . . . . .
C9 C 0.6262(13) 0.9145(13) -0.0456(9) 0.0298(14) Uani 1 1 d . . . . .
H9 H 0.4930 0.8073 -0.0743 0.036 Uiso 1 1 calc R U . . .
C10 C 0.6920(14) 1.0301(14) -0.1671(10) 0.0330(16) Uani 1 1 d . . . . .
H10 H 0.6052 1.0027 -0.2811 0.040 Uiso 1 1 calc R U . . .
C11 C 0.8871(17) 1.1859(15) -0.1183(12) 0.0381(19) Uani 1 1 d . . . . .
H11 H 0.9358 1.2685 -0.1978 0.046 Uiso 1 1 calc R U . . .
C12 C 1.0105(15) 1.2193(13) 0.0497(12) 0.0356(16) Uani 1 1 d . . . . .
H12 H 1.1444 1.3256 0.0824 0.043 Uiso 1 1 calc R U . . .
C13 C 1.1790(13) 1.0256(13) 0.6958(11) 0.0330(15) Uani 1 1 d . . . . .
H13A H 1.2497 0.9940 0.6254 0.050 Uiso 1 1 calc R U . . .
H13B H 1.2606 1.0587 0.8167 0.050 Uiso 1 1 calc R U . . .
H13C H 1.1603 1.1361 0.6591 0.050 Uiso 1 1 calc R U . . .
I1 I 0.52347(8) 0.19818(7) 0.36889(7) 0.03218(11) Uani 1 1 d . . . . .
I2 I 0.19152(7) 0.53852(7) 0.55724(6) 0.03018(11) Uani 1 1 d . . . . .
N1 N 0.7455(10) 0.5963(10) 0.7923(8) 0.0263(11) Uani 1 1 d . . . . .
N2 N 0.8252(11) 0.7970(10) 0.5345(8) 0.0264(12) Uani 1 1 d . . . . .
N3 N 0.8528(11) 0.8935(10) 0.4026(8) 0.0285(12) Uani 1 1 d . . . . .
H3N H 0.9712 0.9951 0.4128 0.034 Uiso 1 1 calc R U . . .
N4 N 0.9490(11) 1.1088(11) 0.1663(9) 0.0310(12) Uani 1 1 d . . . . .
O2 O 0.2307(8) 0.2429(7) 0.4368(6) 0.0202(8) Uani 1 1 d . . . . .
O15 O 0.5284(10) 0.6961(10) 0.2284(8) 0.0364(13) 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
Hg1 O2 2.064(5) . ?
Hg1 N2 2.472(7) . ?
Hg1 N1 2.482(6) . ?
Hg1 I2 2.6710(7) . ?
Hg1 I1 2.6738(8) . ?
C1 N1 1.330(10) . ?
C1 C2 1.385(12) . ?
C1 H1 0.9500 . ?
C2 C3 1.374(14) . ?
C2 H2 0.9500 . ?
C3 C4 1.394(11) . ?
C3 H3 0.9500 . ?
C4 C5 1.406(10) . ?
C4 H4 0.9500 . ?
C5 N1 1.345(10) . ?
C5 C6 1.483(9) . ?
C6 N2 1.294(9) . ?
C6 C13 1.497(11) . ?
C7 O15 1.234(10) . ?
C7 N3 1.372(10) . ?
C7 C8 1.497(10) . ?
C8 N4 1.339(11) . ?
C8 C9 1.380(10) . ?
C9 C10 1.392(11) . ?
C9 H9 0.9500 . ?
C10 C11 1.386(15) . ?
C10 H10 0.9500 . ?
C11 C12 1.395(14) . ?
C11 H11 0.9500 . ?
C12 N4 1.330(11) . ?
C12 H12 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
N2 N3 1.333(9) . ?
N3 H3N 0.8800 . ?

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
O2 Hg1 N2 171.80(19) . . ?
O2 Hg1 N1 120.8(2) . . ?
N2 Hg1 N1 65.5(2) . . ?
O2 Hg1 I2 67.14(14) . . ?
N2 Hg1 I2 117.96(16) . . ?
N1 Hg1 I2 102.06(16) . . ?
O2 Hg1 I1 65.49(14) . . ?
N2 Hg1 I1 108.92(16) . . ?
N1 Hg1 I1 103.14(16) . . ?
I2 Hg1 I1 132.59(3) . . ?
N1 C1 C2 124.1(8) . . ?
N1 C1 H1 118.0 . . ?
C2 C1 H1 118.0 . . ?
C3 C2 C1 117.8(7) . . ?
C3 C2 H2 121.1 . . ?
C1 C2 H2 121.1 . . ?
C2 C3 C4 119.5(8) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C3 C4 C5 118.9(8) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 H4 120.6 . . ?
N1 C5 C4 121.1(6) . . ?
N1 C5 C6 117.4(6) . . ?
C4 C5 C6 121.5(7) . . ?
N2 C6 C5 116.5(6) . . ?
N2 C6 C13 122.8(6) . . ?
C5 C6 C13 120.6(6) . . ?
O15 C7 N3 123.1(7) . . ?
O15 C7 C8 123.9(7) . . ?
N3 C7 C8 113.0(7) . . ?
N4 C8 C9 123.9(7) . . ?
N4 C8 C7 115.7(6) . . ?
C9 C8 C7 120.3(7) . . ?
C8 C9 C10 118.2(8) . . ?
C8 C9 H9 120.9 . . ?
C10 C9 H9 120.9 . . ?
C11 C10 C9 118.6(7) . . ?
C11 C10 H10 120.7 . . ?
C9 C10 H10 120.7 . . ?
C10 C11 C12 118.8(8) . . ?
C10 C11 H11 120.6 . . ?
C12 C11 H11 120.6 . . ?
N4 C12 C11 123.0(9) . . ?
N4 C12 H12 118.5 . . ?
C11 C12 H12 118.5 . . ?
C6 C13 H13A 109.5 . . ?
C6 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C6 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C1 N1 C5 118.6(7) . . ?
C1 N1 Hg1 122.8(6) . . ?
C5 N1 Hg1 118.5(5) . . ?
C6 N2 N3 118.9(7) . . ?
C6 N2 Hg1 121.3(5) . . ?
N3 N2 Hg1 119.6(5) . . ?
N2 N3 C7 120.8(7) . . ?
N2 N3 H3N 119.6 . . ?
C7 N3 H3N 119.6 . . ?
C12 N4 C8 117.5(7) . . ?

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 1.4(13) . . . . ?
C1 C2 C3 C4 -0.4(13) . . . . ?
C2 C3 C4 C5 -0.1(13) . . . . ?
C3 C4 C5 N1 -0.5(12) . . . . ?
C3 C4 C5 C6 177.8(7) . . . . ?
N1 C5 C6 N2 -0.1(9) . . . . ?
C4 C5 C6 N2 -178.5(7) . . . . ?
N1 C5 C6 C13 178.1(7) . . . . ?
C4 C5 C6 C13 -0.2(11) . . . . ?
O15 C7 C8 N4 178.4(8) . . . . ?
N3 C7 C8 N4 -2.2(9) . . . . ?
O15 C7 C8 C9 -3.5(12) . . . . ?
N3 C7 C8 C9 176.0(7) . . . . ?
N4 C8 C9 C10 0.0(12) . . . . ?
C7 C8 C9 C10 -177.9(7) . . . . ?
C8 C9 C10 C11 -0.6(12) . . . . ?
C9 C10 C11 C12 0.8(13) . . . . ?
C10 C11 C12 N4 -0.5(14) . . . . ?
C2 C1 N1 C5 -2.0(12) . . . . ?
C2 C1 N1 Hg1 174.8(6) . . . . ?
C4 C5 N1 C1 1.4(11) . . . . ?
C6 C5 N1 C1 -176.9(7) . . . . ?
C4 C5 N1 Hg1 -175.5(6) . . . . ?
C6 C5 N1 Hg1 6.2(8) . . . . ?
C5 C6 N2 N3 178.4(6) . . . . ?
C13 C6 N2 N3 0.2(11) . . . . ?
C5 C6 N2 Hg1 -6.2(9) . . . . ?
C13 C6 N2 Hg1 175.6(6) . . . . ?
C6 N2 N3 C7 179.3(7) . . . . ?
Hg1 N2 N3 C7 3.8(10) . . . . ?
O15 C7 N3 N2 0.5(12) . . . . ?
C8 C7 N3 N2 -178.9(7) . . . . ?
C11 C12 N4 C8 -0.1(13) . . . . ?
C9 C8 N4 C12 0.3(12) . . . . ?
C7 C8 N4 C12 178.4(7) . . . . ?

_refine_diff_density_max         1.707
_refine_diff_density_min         -1.624
_refine_diff_density_rms         0.174

# start Validation Reply Form
_vrf_PLAT430_6                   
;
PROBLEM: Short Inter D...A Contact  O2.. N4      ..   2.46 Ang.
RESPONSE: This short contact is due to strong hydrogen bonds
present in the structure.
;
# end Validation Reply Form

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_7
_database_code_depnum_ccdc_archive 'CCDC 1506193'
_audit_update_record             
;
2016-09-24 deposited with the CCDC.
2016-10-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H14 Cl2 Hg N4 O'
_chemical_formula_weight         573.82

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Hg Hg -4.2923 7.6849 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   9.2294(3)
_cell_length_b                   11.4544(3)
_cell_length_c                   18.2305(6)
_cell_angle_alpha                80.471(3)
_cell_angle_beta                 77.234(3)
_cell_angle_gamma                87.169(3)
_cell_volume                     1853.54(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5838
_cell_measurement_theta_min      7.82
_cell_measurement_theta_max      124.42

_exptl_crystal_description       Prismatic
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.056
_exptl_crystal_F_000             1088
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    17.675
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.643
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15160
_diffrn_reflns_av_unetI/netI     0.0413
_diffrn_reflns_av_R_equivalents  0.0454
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.914
_diffrn_reflns_theta_max         62.208
_diffrn_reflns_theta_full        68.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.866
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.866
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.866
_reflns_number_total             5838
_reflns_number_gt                5463
_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 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (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)+(0.0683P)²+3.4442P] 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
_refine_ls_extinction_coef       0.00071(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5838
_refine_ls_number_parameters     470
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0349
_refine_ls_wR_factor_ref         0.0927
_refine_ls_wR_factor_gt          0.0904
_refine_ls_goodness_of_fit_ref   0.940
_refine_ls_restrained_S_all      0.940
_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 0.45137(2) 0.76995(2) -0.09444(2) 0.01939(11) Uani 1 1 d . . . . .
Hg2 Hg 1.10893(2) 0.23813(2) 0.49584(2) 0.01862(11) Uani 1 1 d . . . . .
Cl1 Cl 0.42085(17) 0.87818(13) -0.21267(8) 0.0287(3) Uani 1 1 d . . . . .
Cl2 Cl 0.31825(17) 0.59599(12) -0.02518(8) 0.0273(3) Uani 1 1 d . . . . .
Cl3 Cl 1.20869(17) 0.12628(13) 0.59706(8) 0.0291(3) Uani 1 1 d . . . . .
Cl4 Cl 1.1532(2) 0.25626(16) 0.36368(8) 0.0402(4) Uani 1 1 d . . . . .
C1A C 0.7904(6) 0.6879(5) -0.1643(3) 0.0194(12) Uani 1 1 d . . . . .
H1A H 0.7500 0.6914 -0.2070 0.023 Uiso 1 1 calc R U . . .
C1B C 0.7909(6) 0.0971(5) 0.5229(3) 0.0226(12) Uani 1 1 d . . . . .
H1B H 0.8442 0.0639 0.4816 0.027 Uiso 1 1 calc R U . . .
C2A C 0.9339(7) 0.6459(5) -0.1675(3) 0.0240(13) Uani 1 1 d . . . . .
H2A H 0.9878 0.6180 -0.2108 0.029 Uiso 1 1 calc R U . . .
C2B C 0.6546(7) 0.0517(5) 0.5593(4) 0.0271(14) Uani 1 1 d . . . . .
H2B H 0.6166 -0.0108 0.5429 0.033 Uiso 1 1 calc R U . . .
C3A C 0.9960(7) 0.6460(5) -0.1053(4) 0.0269(13) Uani 1 1 d . . . . .
H3A H 1.0934 0.6203 -0.1063 0.032 Uiso 1 1 calc R U . . .
C3B C 0.5745(7) 0.1001(5) 0.6206(3) 0.0248(13) Uani 1 1 d . . . . .
H3B H 0.4815 0.0711 0.6463 0.030 Uiso 1 1 calc R U . . .
C4A C 0.9102(6) 0.6853(5) -0.0410(3) 0.0216(12) Uani 1 1 d . . . . .
H4A H 0.9496 0.6856 0.0017 0.026 Uiso 1 1 calc R U . . .
C4B C 0.6351(6) 0.1925(5) 0.6432(3) 0.0206(12) Uani 1 1 d . . . . .
H4B H 0.5838 0.2264 0.6846 0.025 Uiso 1 1 calc R U . . .
C5A C 0.7665(6) 0.7239(4) -0.0411(3) 0.0145(11) Uani 1 1 d . . . . .
C5B C 0.7735(6) 0.2342(5) 0.6034(3) 0.0161(11) Uani 1 1 d . . . . .
C6A C 0.6707(6) 0.7702(4) 0.0253(3) 0.0137(11) Uani 1 1 d . . . . .
C6B C 0.8434(6) 0.3337(5) 0.6252(3) 0.0148(11) Uani 1 1 d . . . . .
C7A C 0.3170(6) 0.9096(4) 0.0521(3) 0.0151(11) Uani 1 1 d . . . . .
C7B C 1.1808(6) 0.4858(4) 0.5565(3) 0.0153(11) Uani 1 1 d . . . . .
C8A C 0.2196(6) 0.9594(4) 0.1166(3) 0.0160(11) Uani 1 1 d . . . . .
C8B C 1.2581(6) 0.5793(5) 0.5808(3) 0.0153(11) Uani 1 1 d . . . . .
C9A C 0.0778(7) 1.0000(5) 0.1108(4) 0.0256(13) Uani 1 1 d . . . . .
H9A H 0.0419 0.9970 0.0674 0.031 Uiso 1 1 calc R U . . .
C9B C 1.3886(6) 0.6245(5) 0.5350(3) 0.0184(12) Uani 1 1 d . . . . .
H9B H 1.4273 0.5983 0.4889 0.022 Uiso 1 1 calc R U . . .
C10A C -0.0085(7) 1.0455(6) 0.1728(4) 0.0303(15) Uani 1 1 d . . . . .
H10A H -0.1047 1.0728 0.1718 0.036 Uiso 1 1 calc R U . . .
C10B C 1.4613(6) 0.7091(5) 0.5585(3) 0.0240(13) Uani 1 1 d . . . . .
H10B H 1.5503 0.7406 0.5289 0.029 Uiso 1 1 calc R U . . .
C11A C 0.0488(7) 1.0496(5) 0.2347(4) 0.0286(14) Uani 1 1 d . . . . .
H11A H -0.0068 1.0810 0.2762 0.034 Uiso 1 1 calc R U . . .
C11B C 1.3984(7) 0.7457(5) 0.6271(4) 0.0286(14) Uani 1 1 d . . . . .
H11B H 1.4444 0.8026 0.6447 0.034 Uiso 1 1 calc R U . . .
C12A C 0.1921(8) 1.0063(6) 0.2351(4) 0.0301(14) Uani 1 1 d . . . . .
H12A H 0.2301 1.0091 0.2780 0.036 Uiso 1 1 calc R U . . .
C12B C 1.2684(8) 0.6974(5) 0.6685(3) 0.0279(14) Uani 1 1 d . . . . .
H12B H 1.2274 0.7232 0.7145 0.034 Uiso 1 1 calc R U . . .
C13A C 0.7114(6) 0.7513(5) 0.1009(3) 0.0146(11) Uani 1 1 d . . . . .
C13B C 0.7701(6) 0.3807(5) 0.6960(3) 0.0189(12) Uani 1 1 d . . . . .
C14A C 0.7468(7) 0.6373(5) 0.1331(3) 0.0268(13) Uani 1 1 d . . . . .
H14A H 0.7503 0.5750 0.1058 0.032 Uiso 1 1 calc R U . . .
C14B C 0.6546(7) 0.4625(5) 0.6966(3) 0.0243(13) Uani 1 1 d . . . . .
H14B H 0.6256 0.4941 0.6516 0.029 Uiso 1 1 calc R U . . .
C15A C 0.7766(7) 0.6163(6) 0.2047(4) 0.0294(14) Uani 1 1 d . . . . .
H15A H 0.7987 0.5399 0.2260 0.035 Uiso 1 1 calc R U . . .
C15B C 0.5826(7) 0.4969(6) 0.7649(4) 0.0312(14) Uani 1 1 d . . . . .
H15B H 0.5042 0.5512 0.7656 0.037 Uiso 1 1 calc R U . . .
C16A C 0.7735(7) 0.7098(5) 0.2456(3) 0.0244(13) Uani 1 1 d . . . . .
H16A H 0.7930 0.6959 0.2942 0.029 Uiso 1 1 calc R U . . .
C16B C 0.6257(7) 0.4518(5) 0.8320(4) 0.0291(14) Uani 1 1 d . . . . .
H16B H 0.5750 0.4741 0.8777 0.035 Uiso 1 1 calc R U . . .
C17A C 0.7414(6) 0.8226(5) 0.2132(3) 0.0220(12) Uani 1 1 d . . . . .
H17A H 0.7395 0.8848 0.2404 0.026 Uiso 1 1 calc R U . . .
C17B C 0.7444(7) 0.3734(6) 0.8309(3) 0.0288(14) Uani 1 1 d . . . . .
H17B H 0.7756 0.3446 0.8757 0.035 Uiso 1 1 calc R U . . .
C18A C 0.7117(6) 0.8453(5) 0.1407(3) 0.0164(11) Uani 1 1 d . . . . .
H18A H 0.6923 0.9222 0.1189 0.020 Uiso 1 1 calc R U . . .
C18B C 0.8174(6) 0.3374(5) 0.7627(3) 0.0213(12) Uani 1 1 d . . . . .
H18B H 0.8975 0.2847 0.7619 0.026 Uiso 1 1 calc R U . . .
N1A N 0.7069(5) 0.7240(4) -0.1017(2) 0.0158(9) Uani 1 1 d . . . . .
N1B N 0.8509(5) 0.1865(4) 0.5437(3) 0.0174(10) Uani 1 1 d . . . . .
N2A N 0.5487(5) 0.8221(4) 0.0111(2) 0.0138(9) Uani 1 1 d . . . . .
N2B N 0.9688(5) 0.3685(4) 0.5828(2) 0.0139(9) Uani 1 1 d . . . . .
N3A N 0.4489(5) 0.8668(4) 0.0669(2) 0.0166(9) Uani 1 1 d . . . . .
H3NA H 0.4692 0.8679 0.1106 0.020 Uiso 1 1 calc R U . . .
N3B N 1.0434(5) 0.4574(4) 0.5999(3) 0.0166(9) Uani 1 1 d . . . . .
H3NB H 1.0045 0.4943 0.6371 0.020 Uiso 1 1 calc R U . . .
N4A N 0.2774(5) 0.9612(4) 0.1777(3) 0.0218(10) Uani 1 1 d . . . . .
N4B N 1.1947(5) 0.6143(4) 0.6472(3) 0.0219(10) Uani 1 1 d . . . . .
O1A O 0.2823(4) 0.9105(3) -0.0094(2) 0.0208(9) Uani 1 1 d . . . . .
O1B O 1.2376(4) 0.4380(3) 0.5019(2) 0.0223(9) 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
Hg1 Cl1 2.3687(14) . ?
Hg1 N1A 2.370(4) . ?
Hg1 Cl2 2.4078(14) . ?
Hg1 N2A 2.463(4) . ?
Hg1 O1A 2.634(4) . ?
Hg2 Cl4 2.3287(15) . ?
Hg2 Cl3 2.3970(14) . ?
Hg2 N1B 2.415(4) . ?
Hg2 N2B 2.471(4) . ?
Hg2 O1B 2.660(4) . ?
C1A N1A 1.343(7) . ?
C1A C2A 1.379(8) . ?
C1B N1B 1.333(7) . ?
C1B C2B 1.369(9) . ?
C2A C3A 1.380(9) . ?
C2B C3B 1.381(9) . ?
C3A C4A 1.389(8) . ?
C3B C4B 1.381(9) . ?
C4A C5A 1.378(8) . ?
C4B C5B 1.386(8) . ?
C5A N1A 1.339(7) . ?
C5A C6A 1.490(7) . ?
C5B N1B 1.344(7) . ?
C5B C6B 1.487(8) . ?
C6A N2A 1.303(7) . ?
C6A C13A 1.486(7) . ?
C6B N2B 1.282(7) . ?
C6B C13B 1.490(7) . ?
C7A O1A 1.232(7) . ?
C7A N3A 1.355(7) . ?
C7A C8A 1.490(7) . ?
C7B O1B 1.218(7) . ?
C7B N3B 1.361(7) . ?
C7B C8B 1.493(7) . ?
C8A N4A 1.341(7) . ?
C8A C9A 1.387(8) . ?
C8B N4B 1.339(7) . ?
C8B C9B 1.375(8) . ?
C9A C10A 1.393(9) . ?
C9B C10B 1.379(8) . ?
C10A C11A 1.356(10) . ?
C10B C11B 1.380(9) . ?
C11A C12A 1.390(9) . ?
C11B C12B 1.358(9) . ?
C12A N4A 1.326(8) . ?
C12B N4B 1.350(8) . ?
C13A C14A 1.394(8) . ?
C13A C18A 1.395(8) . ?
C13B C14B 1.383(8) . ?
C13B C18B 1.390(8) . ?
C14A C15A 1.372(9) . ?
C14B C15B 1.385(9) . ?
C15A C16A 1.399(9) . ?
C15B C16B 1.381(10) . ?
C16A C17A 1.376(9) . ?
C16B C17B 1.381(10) . ?
C17A C18A 1.390(8) . ?
C17B C18B 1.393(8) . ?
N2A N3A 1.363(6) . ?
N2B N3B 1.370(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Cl1 Hg1 N1A 109.06(11) . . ?
Cl1 Hg1 Cl2 126.80(5) . . ?
N1A Hg1 Cl2 106.16(11) . . ?
Cl1 Hg1 N2A 133.03(10) . . ?
N1A Hg1 N2A 65.83(14) . . ?
Cl2 Hg1 N2A 97.45(10) . . ?
Cl1 Hg1 O1A 95.82(9) . . ?
N1A Hg1 O1A 127.75(13) . . ?
Cl2 Hg1 O1A 92.78(9) . . ?
N2A Hg1 O1A 63.66(13) . . ?
Cl4 Hg2 Cl3 137.29(6) . . ?
Cl4 Hg2 N1B 106.77(12) . . ?
Cl3 Hg2 N1B 98.53(11) . . ?
Cl4 Hg2 N2B 130.42(11) . . ?
Cl3 Hg2 N2B 91.10(11) . . ?
N1B Hg2 N2B 66.08(15) . . ?
Cl4 Hg2 O1B 97.24(10) . . ?
Cl3 Hg2 O1B 93.80(10) . . ?
N1B Hg2 O1B 127.38(13) . . ?
N2B Hg2 O1B 62.71(13) . . ?
N1A C1A C2A 122.4(5) . . ?
N1B C1B C2B 123.3(5) . . ?
C1A C2A C3A 118.6(5) . . ?
C3B C2B C1B 118.9(5) . . ?
C2A C3A C4A 118.8(5) . . ?
C2B C3B C4B 118.7(5) . . ?
C5A C4A C3A 119.5(5) . . ?
C3B C4B C5B 119.2(5) . . ?
N1A C5A C4A 121.4(5) . . ?
N1A C5A C6A 116.6(5) . . ?
C4A C5A C6A 122.0(5) . . ?
N1B C5B C4B 121.8(5) . . ?
N1B C5B C6B 116.9(5) . . ?
C4B C5B C6B 121.3(5) . . ?
N2A C6A C13A 124.7(5) . . ?
N2A C6A C5A 114.0(4) . . ?
C13A C6A C5A 121.2(5) . . ?
N2B C6B C13B 124.7(5) . . ?
N2B C6B C5B 116.3(5) . . ?
C13B C6B C5B 118.9(4) . . ?
O1A C7A N3A 123.4(5) . . ?
O1A C7A C8A 123.0(5) . . ?
N3A C7A C8A 113.6(4) . . ?
O1B C7B N3B 122.8(5) . . ?
O1B C7B C8B 122.1(5) . . ?
N3B C7B C8B 115.1(4) . . ?
N4A C8A C9A 124.1(5) . . ?
N4A C8A C7A 116.2(5) . . ?
C9A C8A C7A 119.7(5) . . ?
N4B C8B C9B 123.8(5) . . ?
N4B C8B C7B 117.1(5) . . ?
C9B C8B C7B 119.2(5) . . ?
C8A C9A C10A 117.2(6) . . ?
C8B C9B C10B 119.0(5) . . ?
C11A C10A C9A 119.5(6) . . ?
C9B C10B C11B 118.2(5) . . ?
C10A C11A C12A 119.0(6) . . ?
C12B C11B C10B 119.0(6) . . ?
N4A C12A C11A 123.5(6) . . ?
N4B C12B C11B 124.3(6) . . ?
C14A C13A C18A 119.6(5) . . ?
C14A C13A C6A 119.4(5) . . ?
C18A C13A C6A 121.0(5) . . ?
C14B C13B C18B 120.2(5) . . ?
C14B C13B C6B 121.5(5) . . ?
C18B C13B C6B 118.3(5) . . ?
C15A C14A C13A 120.6(5) . . ?
C13B C14B C15B 119.3(6) . . ?
C14A C15A C16A 120.1(6) . . ?
C16B C15B C14B 120.9(6) . . ?
C17A C16A C15A 119.4(5) . . ?
C15B C16B C17B 119.7(6) . . ?
C16A C17A C18A 121.2(5) . . ?
C16B C17B C18B 120.0(6) . . ?
C17A C18A C13A 119.2(5) . . ?
C13B C18B C17B 119.7(6) . . ?
C5A N1A C1A 119.1(5) . . ?
C5A N1A Hg1 120.3(3) . . ?
C1A N1A Hg1 120.4(4) . . ?
C1B N1B C5B 118.2(5) . . ?
C1B N1B Hg2 122.1(4) . . ?
C5B N1B Hg2 118.5(3) . . ?
C6A N2A N3A 120.5(4) . . ?
C6A N2A Hg1 118.4(3) . . ?
N3A N2A Hg1 116.7(3) . . ?
C6B N2B N3B 120.3(4) . . ?
C6B N2B Hg2 118.8(4) . . ?
N3B N2B Hg2 118.3(3) . . ?
C7A N3A N2A 118.6(4) . . ?
C7B N3B N2B 118.2(4) . . ?
C12A N4A C8A 116.7(5) . . ?
C8B N4B C12B 115.8(5) . . ?
C7A O1A Hg1 113.0(3) . . ?
C7B O1B Hg2 114.6(3) . . ?

_refine_diff_density_max         2.929
_refine_diff_density_min         -2.427
_refine_diff_density_rms         0.191

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_8
_database_code_depnum_ccdc_archive 'CCDC 1506194'
_audit_update_record             
;
2016-09-24 deposited with the CCDC.
2016-10-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H14 Br2 Hg N4 O'
_chemical_formula_weight         662.74

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Hg Hg -4.2923 7.6849 '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                   9.3269(6)
_cell_length_b                   11.5055(9)
_cell_length_c                   18.7159(12)
_cell_angle_alpha                79.290(6)
_cell_angle_beta                 77.048(6)
_cell_angle_gamma                86.951(6)
_cell_volume                     1923.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    7134
_cell_measurement_theta_min      3.9072
_cell_measurement_theta_max      62.8392

_exptl_crystal_description       Prismatic
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.289
_exptl_crystal_F_000             1232
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    19.349
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.09862
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14662
_diffrn_reflns_av_unetI/netI     0.0501
_diffrn_reflns_av_R_equivalents  0.0504
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.910
_diffrn_reflns_theta_max         62.932
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.881
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.881
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.881
_reflns_number_total             6140
_reflns_number_gt                5616
_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 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (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)+(0.1504P)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         6140
_refine_ls_number_parameters     469
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0739
_refine_ls_R_factor_gt           0.0705
_refine_ls_wR_factor_ref         0.1871
_refine_ls_wR_factor_gt          0.1801
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_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 0.39088(4) 0.26252(3) 0.00265(2) 0.0368(2) Uani 1 1 d . . . . .
Hg2 Hg 0.95070(4) 0.26572(3) 0.41054(2) 0.0358(2) Uani 1 1 d . . . . .
Br1 Br 0.33561(15) 0.25298(12) 0.13814(6) 0.0546(3) Uani 1 1 d . . . . .
Br2 Br 0.29481(13) 0.38037(11) -0.10444(6) 0.0487(3) Uani 1 1 d . . . . .
Br3 Br 0.80675(12) 0.08907(9) 0.48697(6) 0.0460(3) Uani 1 1 d . . . . .
Br4 Br 0.91973(13) 0.37108(10) 0.28616(6) 0.0471(3) Uani 1 1 d . . . . .
C1A C 0.7069(11) 0.3985(8) -0.0219(6) 0.040(2) Uani 1 1 d . . . . .
H1A H 0.6553 0.4299 0.0189 0.048 Uiso 1 1 calc R U . . .
C1B C 1.2861(10) 0.1855(9) 0.3403(5) 0.037(2) Uani 1 1 d . . . . .
H1B H 1.2438 0.1862 0.2997 0.044 Uiso 1 1 calc R U . . .
C2A C 0.8433(12) 0.4471(9) -0.0593(6) 0.045(2) Uani 1 1 d . . . . .
H2A H 0.8820 0.5084 -0.0437 0.054 Uiso 1 1 calc R U . . .
C2B C 1.4302(12) 0.1464(9) 0.3349(6) 0.043(2) Uani 1 1 d . . . . .
H2B H 1.4819 0.1181 0.2929 0.051 Uiso 1 1 calc R U . . .
C3A C 0.9160(12) 0.4023(11) -0.1183(7) 0.050(3) Uani 1 1 d . . . . .
H3A H 1.0055 0.4347 -0.1452 0.060 Uiso 1 1 calc R U . . .
C3B C 1.4949(12) 0.1506(10) 0.3940(6) 0.045(2) Uani 1 1 d . . . . .
H3B H 1.5927 0.1274 0.3917 0.055 Uiso 1 1 calc R U . . .
C4A C 0.8606(11) 0.3086(9) -0.1403(5) 0.039(2) Uani 1 1 d . . . . .
H4A H 0.9134 0.2766 -0.1806 0.047 Uiso 1 1 calc R U . . .
C4B C 1.4117(12) 0.1899(9) 0.4570(6) 0.041(2) Uani 1 1 d . . . . .
H4B H 1.4537 0.1932 0.4972 0.049 Uiso 1 1 calc R U . . .
C5A C 0.7260(11) 0.2638(8) -0.1013(5) 0.0354(19) Uani 1 1 d . . . . .
C5B C 1.2683(10) 0.2237(8) 0.4595(5) 0.0320(19) Uani 1 1 d . . . . .
C6A C 0.6548(10) 0.1664(8) -0.1208(5) 0.0323(18) Uani 1 1 d . . . . .
C6B C 1.1736(10) 0.2696(8) 0.5237(5) 0.0335(19) Uani 1 1 d . . . . .
C7A C 0.3203(10) 0.0160(9) -0.0550(5) 0.0350(19) Uani 1 1 d . . . . .
C7B C 0.8226(11) 0.4084(8) 0.5507(5) 0.0350(19) Uani 1 1 d . . . . .
C8A C 0.2436(11) -0.0752(9) -0.0796(5) 0.038(2) Uani 1 1 d . . . . .
C8B C 0.7267(11) 0.4545(8) 0.6137(5) 0.0350(19) Uani 1 1 d . . . . .
C9A C 0.1126(10) -0.1210(8) -0.0353(6) 0.0346(19) Uani 1 1 d . . . . .
H9A H 0.0713 -0.0947 0.0090 0.042 Uiso 1 1 calc R U . . .
C9B C 0.5854(11) 0.4950(9) 0.6084(6) 0.042(2) Uani 1 1 d . . . . .
H9B H 0.5489 0.4921 0.5665 0.050 Uiso 1 1 calc R U . . .
C10A C 0.0440(11) -0.2071(9) -0.0585(6) 0.041(2) Uani 1 1 d . . . . .
H10A H -0.0442 -0.2401 -0.0303 0.050 Uiso 1 1 calc R U . . .
C10B C 0.4996(12) 0.5410(10) 0.6700(7) 0.050(3) Uani 1 1 d . . . . .
H10B H 0.4045 0.5691 0.6691 0.060 Uiso 1 1 calc R U . . .
C11A C 0.1103(13) -0.2414(10) -0.1238(7) 0.050(3) Uani 1 1 d . . . . .
H11A H 0.0677 -0.2993 -0.1408 0.060 Uiso 1 1 calc R U . . .
C11B C 0.5569(12) 0.5438(9) 0.7299(6) 0.045(2) Uani 1 1 d . . . . .
H11B H 0.5010 0.5719 0.7711 0.054 Uiso 1 1 calc R U . . .
C12A C 0.2382(14) -0.1914(10) -0.1642(6) 0.047(3) Uani 1 1 d . . . . .
H12A H 0.2796 -0.2158 -0.2091 0.057 Uiso 1 1 calc R U . . .
C12B C 0.6998(13) 0.5044(9) 0.7290(6) 0.046(2) Uani 1 1 d . . . . .
H12B H 0.7396 0.5102 0.7695 0.055 Uiso 1 1 calc R U . . .
C13A C 0.7306(10) 0.1199(8) -0.1916(5) 0.0352(19) Uani 1 1 d . . . . .
C13B C 1.2176(10) 0.2490(8) 0.5970(5) 0.0339(19) Uani 1 1 d . . . . .
C14A C 0.8469(13) 0.0397(11) -0.1903(7) 0.053(3) Uani 1 1 d . . . . .
H14A H 0.8756 0.0091 -0.1460 0.063 Uiso 1 1 calc R U . . .
C14B C 1.2563(13) 0.1349(9) 0.6283(6) 0.045(2) Uani 1 1 d . . . . .
H14B H 1.2629 0.0732 0.6019 0.054 Uiso 1 1 calc R U . . .
C15A C 0.9182(12) 0.0068(10) -0.2557(7) 0.051(3) Uani 1 1 d . . . . .
H15A H 0.9981 -0.0451 -0.2558 0.061 Uiso 1 1 calc R U . . .
C15B C 1.2847(14) 0.1149(10) 0.6995(6) 0.048(2) Uani 1 1 d . . . . .
H15B H 1.3085 0.0388 0.7209 0.057 Uiso 1 1 calc R U . . .
C16A C 0.8753(12) 0.0484(10) -0.3211(6) 0.046(2) Uani 1 1 d . . . . .
H16A H 0.9267 0.0263 -0.3653 0.055 Uiso 1 1 calc R U . . .
C16B C 1.2780(12) 0.2052(10) 0.7384(6) 0.042(2) Uani 1 1 d . . . . .
H16B H 1.2975 0.1896 0.7859 0.050 Uiso 1 1 calc R U . . .
C17A C 0.7539(13) 0.1241(11) -0.3209(6) 0.049(3) Uani 1 1 d . . . . .
H17A H 0.7203 0.1498 -0.3645 0.059 Uiso 1 1 calc R U . . .
C17B C 1.2427(12) 0.3199(10) 0.7081(6) 0.044(2) Uani 1 1 d . . . . .
H17B H 1.2389 0.3807 0.7351 0.052 Uiso 1 1 calc R U . . .
C18A C 0.6816(11) 0.1616(9) -0.2537(6) 0.040(2) Uani 1 1 d . . . . .
H18A H 0.6020 0.2139 -0.2527 0.048 Uiso 1 1 calc R U . . .
C18B C 1.2126(10) 0.3432(8) 0.6364(5) 0.0351(19) Uani 1 1 d . . . . .
H18B H 1.1898 0.4197 0.6152 0.042 Uiso 1 1 calc R U . . .
N1A N 0.6469(9) 0.3106(7) -0.0410(5) 0.0391(18) Uani 1 1 d . . . . .
N1B N 1.2028(8) 0.2229(6) 0.4011(4) 0.0311(15) Uani 1 1 d . . . . .
N2A N 0.5299(9) 0.1314(7) -0.0809(4) 0.0365(17) Uani 1 1 d . . . . .
N2B N 1.0534(8) 0.3198(7) 0.5105(4) 0.0301(15) Uani 1 1 d . . . . .
N3A N 0.4569(9) 0.0439(7) -0.0981(5) 0.0392(18) Uani 1 1 d . . . . .
H3A1 H 0.4953 0.0081 -0.1344 0.047 Uiso 1 1 calc R U . . .
N3B N 0.9511(8) 0.3629(7) 0.5649(4) 0.0317(15) Uani 1 1 d . . . . .
H3B1 H 0.9695 0.3606 0.6081 0.038 Uiso 1 1 calc R U . . .
N4A N 0.3086(10) -0.1095(8) -0.1438(5) 0.0425(19) Uani 1 1 d . . . . .
N4B N 0.7836(10) 0.4585(7) 0.6733(4) 0.0398(18) Uani 1 1 d . . . . .
O1A O 0.2625(8) 0.0620(6) -0.0018(4) 0.0422(15) Uani 1 1 d . . . . .
O1B O 0.7874(8) 0.4118(6) 0.4906(4) 0.0409(15) 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
Hg1 N1A 2.403(9) . ?
Hg1 Br1 2.4545(11) . ?
Hg1 N2A 2.482(8) . ?
Hg1 Br2 2.5150(11) . ?
Hg2 N1B 2.351(8) . ?
Hg2 N2B 2.471(7) . ?
Hg2 Br4 2.4875(11) . ?
Hg2 Br3 2.5156(11) . ?
Hg2 O1B 2.652(7) . ?
C1A N1A 1.323(13) . ?
C1A C2A 1.397(16) . ?
C1B N1B 1.354(12) . ?
C1B C2B 1.382(15) . ?
C2A C3A 1.335(17) . ?
C2B C3B 1.382(15) . ?
C3A C4A 1.385(17) . ?
C3B C4B 1.397(16) . ?
C4A C5A 1.376(15) . ?
C4B C5B 1.366(15) . ?
C5A N1A 1.385(13) . ?
C5A C6A 1.473(13) . ?
C5B N1B 1.368(11) . ?
C5B C6B 1.489(13) . ?
C6A N2A 1.275(13) . ?
C6A C13A 1.530(13) . ?
C6B N2B 1.286(13) . ?
C6B C13B 1.492(12) . ?
C7A O1A 1.219(12) . ?
C7A N3A 1.365(13) . ?
C7A C8A 1.494(14) . ?
C7B O1B 1.234(12) . ?
C7B N3B 1.343(13) . ?
C7B C8B 1.477(14) . ?
C8A N4A 1.339(13) . ?
C8A C9A 1.382(14) . ?
C8B N4B 1.346(13) . ?
C8B C9B 1.393(15) . ?
C9A C10A 1.389(14) . ?
C9B C10B 1.419(16) . ?
C10A C11A 1.359(17) . ?
C10B C11B 1.352(17) . ?
C11A C12A 1.354(18) . ?
C11B C12B 1.383(17) . ?
C12A N4A 1.333(14) . ?
C12B N4B 1.332(14) . ?
C13A C18A 1.340(14) . ?
C13A C14A 1.388(16) . ?
C13B C14B 1.398(15) . ?
C13B C18B 1.414(14) . ?
C14A C15A 1.365(17) . ?
C14B C15B 1.391(15) . ?
C15A C16A 1.368(17) . ?
C15B C16B 1.367(16) . ?
C16A C17A 1.391(18) . ?
C16B C17B 1.389(16) . ?
C17A C18A 1.420(15) . ?
C17B C18B 1.407(14) . ?
N2A N3A 1.368(11) . ?
N2B N3B 1.376(11) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1A Hg1 Br1 106.4(2) . . ?
N1A Hg1 N2A 66.5(3) . . ?
Br1 Hg1 N2A 133.50(19) . . ?
N1A Hg1 Br2 98.8(2) . . ?
Br1 Hg1 Br2 135.45(4) . . ?
N2A Hg1 Br2 90.10(19) . . ?
N1B Hg2 N2B 65.3(2) . . ?
N1B Hg2 Br4 107.38(18) . . ?
N2B Hg2 Br4 134.32(18) . . ?
N1B Hg2 Br3 108.59(18) . . ?
N2B Hg2 Br3 97.58(17) . . ?
Br4 Hg2 Br3 125.71(4) . . ?
N1B Hg2 O1B 127.2(2) . . ?
N2B Hg2 O1B 64.0(2) . . ?
Br4 Hg2 O1B 97.21(16) . . ?
Br3 Hg2 O1B 92.07(17) . . ?
N1A C1A C2A 123.9(10) . . ?
N1B C1B C2B 124.1(8) . . ?
C3A C2A C1A 117.7(9) . . ?
C1B C2B C3B 117.8(9) . . ?
C2A C3A C4A 121.3(10) . . ?
C2B C3B C4B 119.2(10) . . ?
C5A C4A C3A 118.7(10) . . ?
C5B C4B C3B 119.8(9) . . ?
C4A C5A N1A 121.0(9) . . ?
C4A C5A C6A 123.4(9) . . ?
N1A C5A C6A 115.6(9) . . ?
C4B C5B N1B 122.1(9) . . ?
C4B C5B C6B 123.0(8) . . ?
N1B C5B C6B 114.8(8) . . ?
N2A C6A C5A 118.3(8) . . ?
N2A C6A C13A 124.0(8) . . ?
C5A C6A C13A 117.5(8) . . ?
N2B C6B C5B 114.4(7) . . ?
N2B C6B C13B 125.7(8) . . ?
C5B C6B C13B 119.8(8) . . ?
O1A C7A N3A 124.0(8) . . ?
O1A C7A C8A 121.9(9) . . ?
N3A C7A C8A 114.1(8) . . ?
O1B C7B N3B 123.3(9) . . ?
O1B C7B C8B 122.7(9) . . ?
N3B C7B C8B 113.9(8) . . ?
N4A C8A C9A 123.5(9) . . ?
N4A C8A C7A 117.2(9) . . ?
C9A C8A C7A 119.3(9) . . ?
N4B C8B C9B 123.1(9) . . ?
N4B C8B C7B 117.3(9) . . ?
C9B C8B C7B 119.5(8) . . ?
C8A C9A C10A 118.5(9) . . ?
C8B C9B C10B 117.0(10) . . ?
C11A C10A C9A 117.8(10) . . ?
C11B C10B C9B 119.6(11) . . ?
C12A C11A C10A 120.0(10) . . ?
C10B C11B C12B 119.0(10) . . ?
N4A C12A C11A 124.3(10) . . ?
N4B C12B C11B 123.5(10) . . ?
C18A C13A C14A 122.5(9) . . ?
C18A C13A C6A 117.3(9) . . ?
C14A C13A C6A 120.3(9) . . ?
C14B C13B C18B 120.1(8) . . ?
C14B C13B C6B 119.8(8) . . ?
C18B C13B C6B 120.1(9) . . ?
C15A C14A C13A 118.4(11) . . ?
C15B C14B C13B 119.2(9) . . ?
C14A C15A C16A 121.7(10) . . ?
C16B C15B C14B 121.1(10) . . ?
C15A C16A C17A 119.3(9) . . ?
C15B C16B C17B 121.1(9) . . ?
C16A C17A C18A 119.4(10) . . ?
C16B C17B C18B 119.4(9) . . ?
C13A C18A C17A 118.6(10) . . ?
C17B C18B C13B 119.2(9) . . ?
C1A N1A C5A 117.4(9) . . ?
C1A N1A Hg1 122.8(7) . . ?
C5A N1A Hg1 118.0(6) . . ?
C1B N1B C5B 117.0(8) . . ?
C1B N1B Hg2 121.3(6) . . ?
C5B N1B Hg2 121.4(6) . . ?
C6A N2A N3A 120.6(8) . . ?
C6A N2A Hg1 117.8(6) . . ?
N3A N2A Hg1 119.1(6) . . ?
C6B N2B N3B 121.7(7) . . ?
C6B N2B Hg2 118.9(6) . . ?
N3B N2B Hg2 114.3(5) . . ?
C7A N3A N2A 117.0(8) . . ?
C7B N3B N2B 120.3(7) . . ?
C12A N4A C8A 115.9(9) . . ?
C12B N4B C8B 117.7(9) . . ?
C7B O1B Hg2 111.9(6) . . ?

_refine_diff_density_max         6.048
_refine_diff_density_min         -2.654
_refine_diff_density_rms         0.358

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_9
_database_code_depnum_ccdc_archive 'CCDC 1506195'
_audit_update_record             
;
2016-09-24 deposited with the CCDC.
2016-10-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H14 Hg I2 N4 O'
_chemical_formula_weight         756.72

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Hg Hg -4.2923 7.6849 '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                   19.9763(2)
_cell_length_b                   11.83920(10)
_cell_length_c                   17.7194(2)
_cell_angle_alpha                90
_cell_angle_beta                 103.3280(10)
_cell_angle_gamma                90
_cell_volume                     4077.83(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    7134
_cell_measurement_theta_min      3.9072
_cell_measurement_theta_max      62.8392

_exptl_crystal_description       Prismatic
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.465
_exptl_crystal_F_000             2752
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_exptl_absorpt_coefficient_mu    37.436
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.09862
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19906
_diffrn_reflns_av_unetI/netI     0.0344
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         4.373
_diffrn_reflns_theta_max         60.207
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.823
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.823
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.823
_reflns_number_total             6070
_reflns_number_gt                5594
_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 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (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)+(0.0385P)²+7.4225P] 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         6070
_refine_ls_number_parameters     469
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0322
_refine_ls_R_factor_gt           0.0290
_refine_ls_wR_factor_ref         0.0728
_refine_ls_wR_factor_gt          0.0708
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
O1A O -0.0007(2) 0.5851(4) 0.1209(2) 0.0299(9) Uani 1 1 d . . . . .
Hg1 Hg 0.09042(2) 0.72285(2) 0.07713(2) 0.02847(9) Uani 1 1 d . . . . .
Hg2 Hg 0.50273(2) 0.73458(2) 0.06364(2) 0.02814(9) Uani 1 1 d . . . . .
I1 I 0.02301(2) 0.90339(4) 0.11355(2) 0.03534(12) Uani 1 1 d . . . . .
I2 I 0.20619(2) 0.61271(4) 0.13253(3) 0.04258(13) Uani 1 1 d . . . . .
I3 I 0.36873(2) 0.71133(4) 0.02247(3) 0.04085(13) Uani 1 1 d . . . . .
I4 I 0.60564(2) 0.65823(4) 0.17872(2) 0.03307(11) Uani 1 1 d . . . . .
C1A C 0.1592(3) 0.7799(5) -0.0758(4) 0.0291(14) Uani 1 1 d . . . . .
H1A H 0.1999 0.7748 -0.0379 0.035 Uiso 1 1 calc R U . . .
C1B C 0.5277(4) 0.5843(5) -0.0888(4) 0.0332(15) Uani 1 1 d . . . . .
H1B H 0.4896 0.5458 -0.0802 0.040 Uiso 1 1 calc R U . . .
C2A C 0.1615(3) 0.8257(5) -0.1469(4) 0.0322(15) Uani 1 1 d . . . . .
H2A H 0.2025 0.8523 -0.1564 0.039 Uiso 1 1 calc R U . . .
C2B C 0.5603(4) 0.5421(6) -0.1438(4) 0.0385(17) Uani 1 1 d . . . . .
H2B H 0.5441 0.4772 -0.1718 0.046 Uiso 1 1 calc R U . . .
C3A C 0.1012(4) 0.8308(5) -0.2033(4) 0.0321(15) Uani 1 1 d . . . . .
H3A H 0.1011 0.8617 -0.2516 0.039 Uiso 1 1 calc R U . . .
C3B C 0.6171(4) 0.5981(6) -0.1563(4) 0.0364(16) Uani 1 1 d . . . . .
H3B H 0.6406 0.5709 -0.1922 0.044 Uiso 1 1 calc R U . . .
C4A C 0.0408(3) 0.7900(5) -0.1881(4) 0.0287(14) Uani 1 1 d . . . . .
H4A H 0.0000 0.7921 -0.2260 0.034 Uiso 1 1 calc R U . . .
C4B C 0.6387(4) 0.6955(5) -0.1146(4) 0.0299(14) Uani 1 1 d . . . . .
H4B H 0.6767 0.7353 -0.1225 0.036 Uiso 1 1 calc R U . . .
C5A C 0.0424(3) 0.7458(5) -0.1152(3) 0.0238(13) Uani 1 1 d . . . . .
C5B C 0.6029(3) 0.7333(5) -0.0606(4) 0.0264(13) Uani 1 1 d . . . . .
C6A C -0.0198(3) 0.6987(5) -0.0947(3) 0.0225(12) Uani 1 1 d . . . . .
C6B C 0.6217(3) 0.8392(5) -0.0169(3) 0.0222(12) Uani 1 1 d . . . . .
C7A C -0.0569(3) 0.5868(5) 0.0756(3) 0.0246(13) Uani 1 1 d . . . . .
C7B C 0.5550(3) 1.0008(5) 0.1155(4) 0.0287(14) Uani 1 1 d . . . . .
C8A C -0.1209(3) 0.5512(5) 0.0980(3) 0.0226(12) Uani 1 1 d . . . . .
C8B C 0.5791(3) 1.1057(5) 0.1610(3) 0.0254(13) Uani 1 1 d . . . . .
C9A C -0.1174(3) 0.5042(5) 0.1708(4) 0.0292(14) Uani 1 1 d . . . . .
H9A H -0.0754 0.4954 0.2062 0.035 Uiso 1 1 calc R U . . .
C9B C 0.5352(4) 1.1605(5) 0.1996(4) 0.0301(14) Uani 1 1 d . . . . .
H9B H 0.4916 1.1319 0.1985 0.036 Uiso 1 1 calc R U . . .
C10A C -0.1778(4) 0.4711(6) 0.1887(4) 0.0348(15) Uani 1 1 d . . . . .
H10A H -0.1775 0.4394 0.2368 0.042 Uiso 1 1 calc R U . . .
C10B C 0.5580(4) 1.2582(5) 0.2394(4) 0.0353(16) Uani 1 1 d . . . . .
H10B H 0.5298 1.2977 0.2654 0.042 Uiso 1 1 calc R U . . .
C11A C -0.2393(4) 0.4856(6) 0.1341(4) 0.0368(16) Uani 1 1 d . . . . .
H11A H -0.2808 0.4634 0.1449 0.044 Uiso 1 1 calc R U . . .
C11B C 0.6226(4) 1.2959(5) 0.2401(4) 0.0366(16) Uani 1 1 d . . . . .
H11B H 0.6395 1.3613 0.2669 0.044 Uiso 1 1 calc R U . . .
C12A C -0.2377(3) 0.5338(6) 0.0634(4) 0.0358(16) Uani 1 1 d . . . . .
H12A H -0.2791 0.5436 0.0272 0.043 Uiso 1 1 calc R U . . .
C12B C 0.6627(4) 1.2357(6) 0.2004(4) 0.0389(17) Uani 1 1 d . . . . .
H12B H 0.7064 1.2631 0.2006 0.047 Uiso 1 1 calc R U . . .
C13A C -0.0862(3) 0.6981(5) -0.1536(3) 0.0235(13) Uani 1 1 d . . . . .
C13B C 0.6867(3) 0.8972(5) -0.0222(4) 0.0292(14) Uani 1 1 d . . . . .
C14A C -0.0972(3) 0.6257(6) -0.2158(4) 0.0362(15) Uani 1 1 d . . . . .
H14A H -0.0628 0.5758 -0.2214 0.043 Uiso 1 1 calc R U . . .
C14B C 0.7492(4) 0.8553(6) 0.0193(4) 0.0371(16) Uani 1 1 d . . . . .
H14B H 0.7502 0.7932 0.0518 0.045 Uiso 1 1 calc R U . . .
C15A C -0.1590(4) 0.6266(6) -0.2700(5) 0.0463(18) Uani 1 1 d . . . . .
H15A H -0.1663 0.5772 -0.3119 0.056 Uiso 1 1 calc R U . . .
C15B C 0.8093(4) 0.9046(7) 0.0129(5) 0.052(2) Uani 1 1 d . . . . .
H15B H 0.8511 0.8767 0.0412 0.063 Uiso 1 1 calc R U . . .
C16A C -0.2101(4) 0.7015(6) -0.2618(4) 0.0412(17) Uani 1 1 d . . . . .
H16A H -0.2520 0.7013 -0.2980 0.049 Uiso 1 1 calc R U . . .
C16B C 0.8081(5) 0.9962(7) -0.0358(6) 0.058(3) Uani 1 1 d . . . . .
H16B H 0.8492 1.0286 -0.0412 0.070 Uiso 1 1 calc R U . . .
C17A C -0.1998(4) 0.7756(7) -0.2012(5) 0.0427(18) Uani 1 1 d . . . . .
H17A H -0.2341 0.8265 -0.1967 0.051 Uiso 1 1 calc R U . . .
C17B C 0.7480(5) 1.0385(7) -0.0751(6) 0.057(2) Uani 1 1 d . . . . .
H17B H 0.7479 1.1013 -0.1066 0.068 Uiso 1 1 calc R U . . .
C18A C -0.1378(4) 0.7743(6) -0.1465(4) 0.0363(16) Uani 1 1 d . . . . .
H18A H -0.1306 0.8242 -0.1049 0.044 Uiso 1 1 calc R U . . .
C18B C 0.6857(4) 0.9908(6) -0.0700(4) 0.0427(17) Uani 1 1 d . . . . .
H18B H 0.6443 1.0207 -0.0978 0.051 Uiso 1 1 calc R U . . .
N1A N 0.1014(3) 0.7429(4) -0.0593(3) 0.0274(11) Uani 1 1 d . . . . .
N1B N 0.5480(3) 0.6768(4) -0.0478(3) 0.0266(11) Uani 1 1 d . . . . .
N2A N -0.0118(3) 0.6630(4) -0.0245(3) 0.0250(11) Uani 1 1 d . . . . .
N2B N 0.5814(3) 0.8732(4) 0.0252(3) 0.0248(11) Uani 1 1 d . . . . .
N3A N -0.0670(3) 0.6213(4) 0.0003(3) 0.0257(11) Uani 1 1 d . . . . .
H3NA H -0.1069 0.6171 -0.0307 0.031 Uiso 1 1 calc R U . . .
N3B N 0.5972(3) 0.9695(4) 0.0684(3) 0.0289(12) Uani 1 1 d . . . . .
H3NB H 0.6327 1.0092 0.0660 0.035 Uiso 1 1 calc R U . . .
N4A N -0.1800(3) 0.5669(4) 0.0446(3) 0.0302(12) Uani 1 1 d . . . . .
N4B N 0.6425(3) 1.1411(4) 0.1619(3) 0.0315(12) Uani 1 1 d . . . . .
O1B O 0.5031(2) 0.9495(4) 0.1195(3) 0.0377(11) 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
O1A C7A 1.221(8) . ?
Hg1 N1A 2.488(5) . ?
Hg1 N2A 2.495(5) . ?
Hg1 I2 2.6392(5) . ?
Hg1 I1 2.6832(5) . ?
Hg2 N1B 2.450(5) . ?
Hg2 N2B 2.474(5) . ?
Hg2 I3 2.6217(5) . ?
Hg2 I4 2.6961(5) . ?
C1A N1A 1.330(8) . ?
C1A C2A 1.381(9) . ?
C1B N1B 1.325(8) . ?
C1B C2B 1.384(10) . ?
C2A C3A 1.378(10) . ?
C2B C3B 1.376(10) . ?
C3A C4A 1.381(9) . ?
C3B C4B 1.385(9) . ?
C4A C5A 1.387(9) . ?
C4B C5B 1.395(9) . ?
C5A N1A 1.353(9) . ?
C5A C6A 1.482(8) . ?
C5B N1B 1.348(8) . ?
C5B C6B 1.476(8) . ?
C6A N2A 1.288(8) . ?
C6A C13A 1.487(9) . ?
C6B N2B 1.283(8) . ?
C6B C13B 1.490(9) . ?
C7A N3A 1.365(8) . ?
C7A C8A 1.484(8) . ?
C7B O1B 1.217(8) . ?
C7B N3B 1.367(8) . ?
C7B C8B 1.498(9) . ?
C8A N4A 1.345(8) . ?
C8A C9A 1.392(9) . ?
C8B N4B 1.332(8) . ?
C8B C9B 1.390(9) . ?
C9A C10A 1.375(9) . ?
C9B C10B 1.377(10) . ?
C10A C11A 1.387(10) . ?
C10B C11B 1.365(11) . ?
C11A C12A 1.384(10) . ?
C11B C12B 1.379(10) . ?
C12A N4A 1.329(8) . ?
C12B N4B 1.325(9) . ?
C13A C14A 1.372(9) . ?
C13A C18A 1.399(9) . ?
C13B C14B 1.387(10) . ?
C13B C18B 1.392(10) . ?
C14A C15A 1.378(10) . ?
C14B C15B 1.363(11) . ?
C15A C16A 1.385(11) . ?
C15B C16B 1.381(13) . ?
C16A C17A 1.365(11) . ?
C16B C17B 1.339(14) . ?
C17A C18A 1.385(11) . ?
C17B C18B 1.387(11) . ?
N2A N3A 1.368(7) . ?
N2B N3B 1.369(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1A Hg1 N2A 64.30(16) . . ?
N1A Hg1 I2 98.22(12) . . ?
N2A Hg1 I2 129.03(11) . . ?
N1A Hg1 I1 108.60(12) . . ?
N2A Hg1 I1 91.55(11) . . ?
I2 Hg1 I1 138.541(17) . . ?
N1B Hg2 N2B 65.65(15) . . ?
N1B Hg2 I3 106.81(12) . . ?
N2B Hg2 I3 131.72(12) . . ?
N1B Hg2 I4 99.05(13) . . ?
N2B Hg2 I4 90.51(12) . . ?
I3 Hg2 I4 136.622(16) . . ?
N1A C1A C2A 122.9(6) . . ?
N1B C1B C2B 123.5(6) . . ?
C3A C2A C1A 118.2(6) . . ?
C3B C2B C1B 118.5(6) . . ?
C2A C3A C4A 119.9(6) . . ?
C2B C3B C4B 118.9(6) . . ?
C3A C4A C5A 118.6(6) . . ?
C3B C4B C5B 119.1(6) . . ?
N1A C5A C4A 121.4(5) . . ?
N1A C5A C6A 116.5(5) . . ?
C4A C5A C6A 122.0(6) . . ?
N1B C5B C4B 121.6(6) . . ?
N1B C5B C6B 116.9(5) . . ?
C4B C5B C6B 121.5(5) . . ?
N2A C6A C5A 116.0(5) . . ?
N2A C6A C13A 124.6(5) . . ?
C5A C6A C13A 119.4(5) . . ?
N2B C6B C5B 116.9(5) . . ?
N2B C6B C13B 124.4(5) . . ?
C5B C6B C13B 118.6(5) . . ?
O1A C7A N3A 123.6(5) . . ?
O1A C7A C8A 122.5(5) . . ?
N3A C7A C8A 113.9(5) . . ?
O1B C7B N3B 123.6(6) . . ?
O1B C7B C8B 123.7(5) . . ?
N3B C7B C8B 112.7(5) . . ?
N4A C8A C9A 123.7(5) . . ?
N4A C8A C7A 116.3(5) . . ?
C9A C8A C7A 119.9(5) . . ?
N4B C8B C9B 123.6(6) . . ?
N4B C8B C7B 117.0(5) . . ?
C9B C8B C7B 119.4(6) . . ?
C10A C9A C8A 118.0(6) . . ?
C10B C9B C8B 118.3(6) . . ?
C9A C10A C11A 119.1(6) . . ?
C11B C10B C9B 118.6(6) . . ?
C12A C11A C10A 118.7(6) . . ?
C10B C11B C12B 119.1(6) . . ?
N4A C12A C11A 123.4(6) . . ?
N4B C12B C11B 123.8(7) . . ?
C14A C13A C18A 119.3(6) . . ?
C14A C13A C6A 121.3(5) . . ?
C18A C13A C6A 119.4(6) . . ?
C14B C13B C18B 119.5(6) . . ?
C14B C13B C6B 119.5(6) . . ?
C18B C13B C6B 121.0(6) . . ?
C13A C14A C15A 120.5(6) . . ?
C15B C14B C13B 120.3(7) . . ?
C14A C15A C16A 119.7(7) . . ?
C14B C15B C16B 120.0(8) . . ?
C17A C16A C15A 120.9(7) . . ?
C17B C16B C15B 120.1(7) . . ?
C16A C17A C18A 119.4(6) . . ?
C16B C17B C18B 121.6(8) . . ?
C17A C18A C13A 120.2(7) . . ?
C17B C18B C13B 118.4(8) . . ?
C1A N1A C5A 118.9(5) . . ?
C1A N1A Hg1 121.4(4) . . ?
C5A N1A Hg1 117.3(4) . . ?
C1B N1B C5B 118.3(5) . . ?
C1B N1B Hg2 123.4(4) . . ?
C5B N1B Hg2 117.6(4) . . ?
C6A N2A N3A 120.0(5) . . ?
C6A N2A Hg1 120.1(4) . . ?
N3A N2A Hg1 117.1(3) . . ?
C6B N2B N3B 119.5(5) . . ?
C6B N2B Hg2 118.4(4) . . ?
N3B N2B Hg2 118.5(3) . . ?
C7A N3A N2A 118.3(5) . . ?
C7B N3B N2B 118.2(5) . . ?
C12A N4A C8A 117.0(5) . . ?
C12B N4B C8B 116.6(6) . . ?

_refine_diff_density_max         1.494
_refine_diff_density_min         -1.089
_refine_diff_density_rms         0.152

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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 1506196'
_audit_update_record             
;
2016-09-24 deposited with the CCDC.
2016-10-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H10 Br2 Hg N4 O'
_chemical_formula_weight         586.65

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/n

loop_
_symmetry_equiv_pos_as_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                   7.3839(7)
_cell_length_b                   12.5740(11)
_cell_length_c                   15.6783(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.892(5)
_cell_angle_gamma                90.00
_cell_volume                     1454.9(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1964
_cell_measurement_theta_min      2.6
_cell_measurement_theta_max      24.37

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.678
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1072
_exptl_absorpt_coefficient_mu    16.072
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.1078
_exptl_absorpt_correction_T_max  0.2119
_exptl_absorpt_process_details   'BRUKER SADABS'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(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 APPEX-II CCD'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            2985
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0408
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.60
_diffrn_reflns_theta_max         26.44
_reflns_number_total             2985
_reflns_number_gt                2523
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'APPEX2 (BRUKER AXS, 2005)'
_computing_cell_refinement       'APPEX2 (BRUKER AXS, 2005)'
_computing_data_reduction        'APPEX2 (BRUKER AXS, 2005)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0203P)²+4.4775P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2985
_refine_ls_number_parameters     185
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0400
_refine_ls_R_factor_gt           0.0300
_refine_ls_wR_factor_ref         0.0600
_refine_ls_wR_factor_gt          0.0575
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.0647(8) 0.1908(5) 0.0373(4) 0.0200(13) Uani 1 1 d . . .
H1 H -0.0120 0.2590 0.0300 0.024 Uiso 1 1 calc R . .
C2 C -0.1816(8) 0.1526(5) -0.0261(4) 0.0213(14) Uani 1 1 d . . .
H2 H -0.2085 0.1937 -0.0757 0.026 Uiso 1 1 calc R . .
C3 C -0.2580(8) 0.0546(5) -0.0160(4) 0.0215(14) Uani 1 1 d . . .
H3 H -0.3368 0.0259 -0.0592 0.026 Uiso 1 1 calc R . .
C4 C -0.2196(8) -0.0019(5) 0.0573(4) 0.0200(14) Uani 1 1 d . . .
H4 H -0.2742 -0.0693 0.0662 0.024 Uiso 1 1 calc R . .
C5 C -0.1002(8) 0.0406(5) 0.1182(3) 0.0166(13) Uani 1 1 d . . .
C6 C -0.0570(8) -0.0160(5) 0.1975(4) 0.0184(13) Uani 1 1 d . . .
H6 H -0.1058 -0.0847 0.2070 0.022 Uiso 1 1 calc R . .
C7 C 0.1820(8) 0.0271(5) 0.3910(3) 0.0177(13) Uani 1 1 d . . .
C8 C 0.2055(8) -0.0384(5) 0.4703(3) 0.0163(13) Uani 1 1 d . . .
C9 C 0.3017(8) 0.0014(5) 0.5403(4) 0.0197(14) Uani 1 1 d . . .
H9 H 0.3536 0.0705 0.5395 0.024 Uiso 1 1 calc R . .
C10 C 0.3197(8) -0.0630(5) 0.6118(4) 0.0203(14) Uani 1 1 d . . .
H10 H 0.3864 -0.0392 0.6610 0.024 Uiso 1 1 calc R . .
C11 C 0.2404(8) -0.1611(5) 0.6104(4) 0.0237(15) Uani 1 1 d . . .
H11 H 0.2517 -0.2070 0.6584 0.028 Uiso 1 1 calc R . .
C12 C 0.1427(9) -0.1924(5) 0.5374(4) 0.0232(14) Uani 1 1 d . . .
H12 H 0.0846 -0.2598 0.5374 0.028 Uiso 1 1 calc R . .
Br1 Br 0.50602(9) 0.18088(5) 0.18400(4) 0.02646(16) Uani 1 1 d . . .
Br2 Br 0.02144(9) 0.36284(5) 0.26912(4) 0.02176(15) Uani 1 1 d . . .
Hg1 Hg 0.18237(3) 0.197520(19) 0.222966(14) 0.01919(8) Uani 1 1 d . . .
N1 N -0.0223(6) 0.1366(4) 0.1080(3) 0.0156(11) Uani 1 1 d . . .
N2 N 0.0459(7) 0.0272(4) 0.2533(3) 0.0195(11) Uani 1 1 d . . .
N3 N 0.0820(7) -0.0231(4) 0.3284(3) 0.0181(12) Uani 1 1 d . . .
N4 N 0.1265(7) -0.1329(4) 0.4674(3) 0.0205(12) Uani 1 1 d . . .
O1 O 0.2474(6) 0.1152(3) 0.3819(2) 0.0214(10) Uani 1 1 d . . .
H3N H 0.047(8) -0.078(5) 0.342(4) 0.011(17) Uiso 1 1 d . . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 1.330(7) . ?
C1 C2 1.380(8) . ?
C1 H1 0.9500 . ?
C2 C3 1.367(9) . ?
C2 H2 0.9500 . ?
C3 C4 1.373(8) . ?
C3 H3 0.9500 . ?
C4 C5 1.385(8) . ?
C4 H4 0.9500 . ?
C5 N1 1.349(7) . ?
C5 C6 1.458(8) . ?
C6 N2 1.263(7) . ?
C6 H6 0.9500 . ?
C7 O1 1.220(7) . ?
C7 N3 1.363(8) . ?
C7 C8 1.497(8) . ?
C8 N4 1.324(7) . ?
C8 C9 1.381(8) . ?
C9 C10 1.385(8) . ?
C9 H9 0.9500 . ?
C10 C11 1.365(9) . ?
C10 H10 0.9500 . ?
C11 C12 1.390(9) . ?
C11 H11 0.9500 . ?
C12 N4 1.330(7) . ?
C12 H12 0.9500 . ?
Br1 Hg1 2.4949(7) . ?
Br2 Hg1 2.5127(7) . ?
Hg1 N2 2.421(5) . ?
Hg1 N1 2.437(5) . ?
N2 N3 1.355(7) . ?
N3 H3N 0.77(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 123.1(6) . . ?
N1 C1 H1 118.5 . . ?
C2 C1 H1 118.5 . . ?
C3 C2 C1 118.8(6) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 H2 120.6 . . ?
C2 C3 C4 119.3(6) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C3 C4 C5 119.1(6) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
N1 C5 C4 121.8(5) . . ?
N1 C5 C6 117.1(5) . . ?
C4 C5 C6 121.0(5) . . ?
N2 C6 C5 119.4(6) . . ?
N2 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
O1 C7 N3 123.0(5) . . ?
O1 C7 C8 124.2(5) . . ?
N3 C7 C8 112.8(5) . . ?
N4 C8 C9 124.5(5) . . ?
N4 C8 C7 115.2(5) . . ?
C9 C8 C7 120.2(5) . . ?
C8 C9 C10 117.7(6) . . ?
C8 C9 H9 121.2 . . ?
C10 C9 H9 121.2 . . ?
C11 C10 C9 119.0(6) . . ?
C11 C10 H10 120.5 . . ?
C9 C10 H10 120.5 . . ?
C10 C11 C12 118.7(6) . . ?
C10 C11 H11 120.6 . . ?
C12 C11 H11 120.6 . . ?
N4 C12 C11 123.3(6) . . ?
N4 C12 H12 118.3 . . ?
C11 C12 H12 118.3 . . ?
N2 Hg1 N1 67.38(16) . . ?
N2 Hg1 Br1 112.47(11) . . ?
N1 Hg1 Br1 111.59(11) . . ?
N2 Hg1 Br2 118.13(11) . . ?
N1 Hg1 Br2 100.70(11) . . ?
Br1 Hg1 Br2 127.29(2) . . ?
C1 N1 C5 117.9(5) . . ?
C1 N1 Hg1 125.3(4) . . ?
C5 N1 Hg1 116.7(4) . . ?
C6 N2 N3 119.9(5) . . ?
C6 N2 Hg1 119.3(4) . . ?
N3 N2 Hg1 120.8(4) . . ?
N2 N3 C7 119.7(5) . . ?
N2 N3 H3N 127(4) . . ?
C7 N3 H3N 113(4) . . ?
C8 N4 C12 116.7(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
N1 C1 C2 C3 0.1(9) . . . . ?
C1 C2 C3 C4 1.4(9) . . . . ?
C2 C3 C4 C5 -1.8(9) . . . . ?
C3 C4 C5 N1 0.8(9) . . . . ?
C3 C4 C5 C6 179.3(5) . . . . ?
N1 C5 C6 N2 1.8(8) . . . . ?
C4 C5 C6 N2 -176.8(5) . . . . ?
O1 C7 C8 N4 -178.9(5) . . . . ?
N3 C7 C8 N4 -0.3(7) . . . . ?
O1 C7 C8 C9 2.1(9) . . . . ?
N3 C7 C8 C9 -179.2(5) . . . . ?
N4 C8 C9 C10 1.4(9) . . . . ?
C7 C8 C9 C10 -179.7(5) . . . . ?
C8 C9 C10 C11 -1.0(9) . . . . ?
C9 C10 C11 C12 -0.6(9) . . . . ?
C10 C11 C12 N4 2.0(10) . . . . ?
C2 C1 N1 C5 -1.1(8) . . . . ?
C2 C1 N1 Hg1 -180.0(4) . . . . ?
C4 C5 N1 C1 0.6(8) . . . . ?
C6 C5 N1 C1 -177.9(5) . . . . ?
C4 C5 N1 Hg1 179.6(4) . . . . ?
C6 C5 N1 Hg1 1.1(6) . . . . ?
N2 Hg1 N1 C1 176.9(5) . . . . ?
Br1 Hg1 N1 C1 -76.8(5) . . . . ?
Br2 Hg1 N1 C1 60.7(5) . . . . ?
N2 Hg1 N1 C5 -2.0(4) . . . . ?
Br1 Hg1 N1 C5 104.3(4) . . . . ?
Br2 Hg1 N1 C5 -118.2(4) . . . . ?
C5 C6 N2 N3 177.8(5) . . . . ?
C5 C6 N2 Hg1 -3.8(7) . . . . ?
N1 Hg1 N2 C6 3.1(4) . . . . ?
Br1 Hg1 N2 C6 -101.9(4) . . . . ?
Br2 Hg1 N2 C6 93.4(4) . . . . ?
N1 Hg1 N2 N3 -178.5(4) . . . . ?
Br1 Hg1 N2 N3 76.5(4) . . . . ?
Br2 Hg1 N2 N3 -88.2(4) . . . . ?
C6 N2 N3 C7 -175.1(5) . . . . ?
Hg1 N2 N3 C7 6.5(7) . . . . ?
O1 C7 N3 N2 -2.7(9) . . . . ?
C8 C7 N3 N2 178.6(5) . . . . ?
C9 C8 N4 C12 -0.2(9) . . . . ?
C7 C8 N4 C12 -179.1(5) . . . . ?
C11 C12 N4 C8 -1.6(9) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        26.44
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         1.275
_refine_diff_density_min         -1.031
_refine_diff_density_rms         0.181
####################################################################### 
# 
# 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 1506197'
_audit_update_record             
;
2016-09-24 deposited with the CCDC.
2016-10-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H14 Br2 Hg N4 O2'
_chemical_formula_weight         618.69

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'
Hg Hg -2.3894 9.2266 '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'

_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                   8.8275(2)
_cell_length_b                   9.8653(2)
_cell_length_c                   10.7261(3)
_cell_angle_alpha                92.093(2)
_cell_angle_beta                 91.266(2)
_cell_angle_gamma                114.7120(10)
_cell_volume                     847.26(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6607
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      23.89

_exptl_crystal_description       prismatic
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.425
_exptl_crystal_F_000             572
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.17
_exptl_absorpt_coefficient_mu    13.810
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.0856
_exptl_absorpt_correction_T_max  0.2024
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus 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            20722
_diffrn_reflns_av_unetI/netI     0.0505
_diffrn_reflns_av_R_equivalents  0.0476
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.901
_diffrn_reflns_theta_max         30.533
_diffrn_reflns_theta_full        25.240
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             5162
_reflns_number_gt                3782
_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    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (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)+(0.0689P)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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5162
_refine_ls_number_parameters     200
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0679
_refine_ls_R_factor_gt           0.0398
_refine_ls_wR_factor_ref         0.1246
_refine_ls_wR_factor_gt          0.0963
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.064
_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 0.53762(3) 0.17374(3) 0.17266(2) 0.04540(11) Uani 1 1 d . . . . .
Br1 Br 0.78192(9) 0.20474(9) 0.31069(7) 0.0585(2) Uani 1 1 d . . . . .
Br2 Br 0.28346(10) -0.00033(8) 0.05170(7) 0.05515(19) Uani 1 1 d . . . . .
C1 C 0.7673(9) 0.4067(8) -0.0523(6) 0.0498(16) Uani 1 1 d . . . . .
H1 H 0.7689 0.3182 -0.0838 0.060 Uiso 1 1 calc R U . . .
C2 C 0.8587(9) 0.5365(8) -0.1099(7) 0.0536(17) Uani 1 1 d . . . . .
H2 H 0.9207 0.5349 -0.1785 0.064 Uiso 1 1 calc R U . . .
C3 C 0.8580(8) 0.6666(8) -0.0662(6) 0.0492(16) Uani 1 1 d . . . . .
H3 H 0.9202 0.7558 -0.1033 0.059 Uiso 1 1 calc R U . . .
C4 C 0.7617(8) 0.6635(7) 0.0357(6) 0.0436(14) Uani 1 1 d . . . . .
H4 H 0.7576 0.7511 0.0667 0.052 Uiso 1 1 calc R U . . .
C5 C 0.6724(7) 0.5302(7) 0.0905(5) 0.0359(12) Uani 1 1 d . . . . .
C6 C 0.5699(7) 0.5246(7) 0.1961(5) 0.0370(12) Uani 1 1 d . . . . .
H6 H 0.5599 0.6103 0.2255 0.044 Uiso 1 1 calc R U . . .
C7 C 0.3214(7) 0.2659(7) 0.4033(5) 0.0390(13) Uani 1 1 d . . . . .
C8 C 0.2109(7) 0.2652(7) 0.5069(5) 0.0377(12) Uani 1 1 d . . . . .
C9 C 0.1464(8) 0.1408(8) 0.5775(6) 0.0456(14) Uani 1 1 d . . . . .
H9 H 0.1720 0.0594 0.5623 0.055 Uiso 1 1 calc R U . . .
C10 C 0.0417(8) 0.1417(9) 0.6723(6) 0.0536(17) Uani 1 1 d . . . . .
H10 H -0.0021 0.0621 0.7243 0.064 Uiso 1 1 calc R U . . .
C11 C 0.0047(9) 0.2636(10) 0.6870(7) 0.0566(19) Uani 1 1 d . . . . .
H11 H -0.0673 0.2659 0.7482 0.068 Uiso 1 1 calc R U . . .
C12 C 0.0737(9) 0.3817(10) 0.6116(7) 0.0556(17) Uani 1 1 d . . . . .
H12 H 0.0473 0.4630 0.6237 0.067 Uiso 1 1 calc R U . . .
N1 N 0.6754(6) 0.4016(5) 0.0478(4) 0.0383(11) Uani 1 1 d . . . . .
N2 N 0.4935(6) 0.4011(6) 0.2484(4) 0.0350(10) Uani 1 1 d . . . . .
N3 N 0.3955(6) 0.3963(6) 0.3465(4) 0.0381(11) Uani 1 1 d . . . . .
H3A H 0.3814 0.4740 0.3714 0.046 Uiso 1 1 calc R U . . .
N4 N 0.1784(7) 0.3851(6) 0.5205(5) 0.0463(12) Uani 1 1 d D . . . .
O1 O 0.3405(6) 0.1525(5) 0.3711(4) 0.0543(12) Uani 1 1 d . . . . .
O1M O 0.3650(8) 0.6772(6) 0.3903(5) 0.0677(15) Uani 1 1 d D . . . .
H1M H 0.3314 0.6939 0.4736 0.081 Uiso 1 1 d DR U . . .
C1M C 0.4325(10) 0.8281(9) 0.3652(8) 0.064(2) Uani 1 1 d D . . . .
H1M1 H 0.3443 0.8595 0.3518 0.096 Uiso 1 1 d R U . . .
H1M2 H 0.4959 0.8424 0.2914 0.096 Uiso 1 1 d R U . . .
H1M3 H 0.5041 0.8861 0.4342 0.096 Uiso 1 1 d 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 Br2 2.4806(8) . ?
Hg1 Br1 2.4921(8) . ?
Hg1 N1 2.517(5) . ?
Hg1 N2 2.541(5) . ?
C1 N1 1.350(8) . ?
C1 C2 1.374(10) . ?
C2 C3 1.353(11) . ?
C3 C4 1.393(9) . ?
C4 C5 1.381(8) . ?
C5 N1 1.344(8) . ?
C5 C6 1.454(8) . ?
C6 N2 1.278(7) . ?
C7 O1 1.237(8) . ?
C7 N3 1.351(8) . ?
C7 C8 1.493(8) . ?
C8 N4 1.333(8) . ?
C8 C9 1.381(9) . ?
C9 C10 1.391(9) . ?
C10 C11 1.377(11) . ?
C11 C12 1.370(11) . ?
C12 N4 1.351(8) . ?
N2 N3 1.367(6) . ?
O1M C1M 1.392(9) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Br2 Hg1 Br1 147.38(3) . . ?
Br2 Hg1 N1 107.51(12) . . ?
Br1 Hg1 N1 98.61(12) . . ?
Br2 Hg1 N2 108.72(11) . . ?
Br1 Hg1 N2 99.81(11) . . ?
N1 Hg1 N2 64.86(15) . . ?
N1 C1 C2 123.1(6) . . ?
C3 C2 C1 119.6(6) . . ?
C2 C3 C4 118.2(6) . . ?
C5 C4 C3 120.0(6) . . ?
N1 C5 C4 121.5(6) . . ?
N1 C5 C6 117.8(5) . . ?
C4 C5 C6 120.7(6) . . ?
N2 C6 C5 119.5(5) . . ?
O1 C7 N3 122.8(5) . . ?
O1 C7 C8 121.4(6) . . ?
N3 C7 C8 115.8(6) . . ?
N4 C8 C9 125.3(6) . . ?
N4 C8 C7 116.2(5) . . ?
C9 C8 C7 118.5(6) . . ?
C8 C9 C10 117.5(6) . . ?
C11 C10 C9 118.2(7) . . ?
C12 C11 C10 120.1(6) . . ?
N4 C12 C11 122.9(7) . . ?
C5 N1 C1 117.6(5) . . ?
C5 N1 Hg1 118.2(4) . . ?
C1 N1 Hg1 123.8(4) . . ?
C6 N2 N3 119.1(5) . . ?
C6 N2 Hg1 119.0(4) . . ?
N3 N2 Hg1 121.8(3) . . ?
C7 N3 N2 118.0(5) . . ?
C8 N4 C12 116.0(6) . . ?

_refine_diff_density_max         1.324
_refine_diff_density_min         -2.861
_refine_diff_density_rms         0.478

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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 1506198'
_audit_update_record             
;
2016-09-24 deposited with the CCDC.
2016-10-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H12 Cl2 Hg N4 O'
_chemical_formula_weight         511.76

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'
Cl Cl 0.1484 0.1585 '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                   7.9297(16)
_cell_length_b                   13.566(3)
_cell_length_c                   14.212(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.29(3)
_cell_angle_gamma                90
_cell_volume                     1528.8(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5814
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      24.16

_exptl_crystal_description       prismatic
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.223
_exptl_crystal_F_000             960
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_exptl_absorpt_coefficient_mu    10.419
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.0841
_exptl_absorpt_correction_T_max  0.2154
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus 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            13584
_diffrn_reflns_av_unetI/netI     0.0311
_diffrn_reflns_av_R_equivalents  0.0218
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.867
_diffrn_reflns_theta_max         36.283
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             7077
_reflns_number_gt                5295
_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    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (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)+(0.0264P)²+0.4050P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7077
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0478
_refine_ls_R_factor_gt           0.0266
_refine_ls_wR_factor_ref         0.0591
_refine_ls_wR_factor_gt          0.0540
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_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 0.81878(2) 0.31186(2) 0.21028(2) 0.03162(3) Uani 1 1 d . . . . .
Cl1 Cl 0.54712(8) 0.34643(6) 0.14838(5) 0.04287(14) Uani 1 1 d . . . . .
Cl2 Cl 0.95213(9) 0.16246(5) 0.25856(5) 0.04078(14) Uani 1 1 d . . . . .
C1 C 1.0881(3) 0.31220(16) 0.03200(18) 0.0347(5) Uani 1 1 d . . . . .
H1 H 1.0439 0.2491 0.0254 0.042 Uiso 1 1 calc R U . . .
C2 C 1.2096(3) 0.34357(19) -0.03139(17) 0.0359(5) Uani 1 1 d . . . . .
H2 H 1.2469 0.3023 -0.0792 0.043 Uiso 1 1 calc R U . . .
C3 C 1.2733(3) 0.43777(19) -0.02143(17) 0.0360(5) Uani 1 1 d . . . . .
H3 H 1.3528 0.4616 -0.0635 0.043 Uiso 1 1 calc R U . . .
C4 C 1.2176(3) 0.49622(17) 0.05172(16) 0.0311(4) Uani 1 1 d . . . . .
H4 H 1.2606 0.5595 0.0598 0.037 Uiso 1 1 calc R U . . .
C5 C 1.0971(3) 0.45988(15) 0.11316(14) 0.0253(4) Uani 1 1 d . . . . .
C6 C 1.0372(3) 0.51705(15) 0.19601(15) 0.0257(4) Uani 1 1 d . . . . .
C7 C 0.8000(3) 0.46513(16) 0.39838(15) 0.0276(4) Uani 1 1 d . . . . .
C8 C 0.7721(3) 0.52387(16) 0.48617(15) 0.0273(4) Uani 1 1 d . . . . .
C9 C 0.6794(3) 0.48683(18) 0.56012(16) 0.0321(5) Uani 1 1 d . . . . .
H9 H 0.6326 0.4240 0.5569 0.039 Uiso 1 1 calc R U . . .
C10 C 0.6576(3) 0.54507(18) 0.63916(17) 0.0351(5) Uani 1 1 d . . . . .
H10 H 0.5932 0.5229 0.6894 0.042 Uiso 1 1 calc R U . . .
C11 C 0.7333(3) 0.63692(18) 0.64187(16) 0.0344(5) Uani 1 1 d . . . . .
H11 H 0.7231 0.6771 0.6946 0.041 Uiso 1 1 calc R U . . .
C12 C 0.8249(4) 0.66787(18) 0.56427(19) 0.0380(6) Uani 1 1 d . . . . .
H12 H 0.8753 0.7298 0.5662 0.046 Uiso 1 1 calc R U . . .
C13 C 1.0934(3) 0.62116(17) 0.21096(18) 0.0360(5) Uani 1 1 d . . . . .
H13A H 1.0010 0.6594 0.2347 0.054 Uiso 1 1 d R U . . .
H13B H 1.1303 0.6485 0.1523 0.054 Uiso 1 1 d R U . . .
H13C H 1.1848 0.6224 0.2555 0.054 Uiso 1 1 d R U . . .
N1 N 1.0322(2) 0.36894(13) 0.10214(13) 0.0286(4) Uani 1 1 d . . . . .
N2 N 0.9430(2) 0.46969(13) 0.25365(12) 0.0257(3) Uani 1 1 d . . . . .
N3 N 0.8943(2) 0.51450(14) 0.33487(12) 0.0290(4) Uani 1 1 d . . . . .
H3N H 0.9237 0.5744 0.3458 0.035 Uiso 1 1 calc R U . . .
N4 N 0.8442(3) 0.61323(14) 0.48707(14) 0.0330(4) Uani 1 1 d . . . . .
O1 O 0.7451(2) 0.38166(12) 0.38613(12) 0.0359(4) 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
Hg1 Cl1 2.3696(9) . ?
Hg1 Cl2 2.3853(8) . ?
Hg1 N1 2.4188(19) . ?
Hg1 N2 2.4348(19) . ?
C1 N1 1.337(3) . ?
C1 C2 1.389(3) . ?
C2 C3 1.381(4) . ?
C3 C4 1.382(3) . ?
C4 C5 1.388(3) . ?
C5 N1 1.346(3) . ?
C5 C6 1.490(3) . ?
C6 N2 1.284(3) . ?
C6 C13 1.496(3) . ?
C7 O1 1.225(3) . ?
C7 N3 1.353(3) . ?
C7 C8 1.498(3) . ?
C8 N4 1.340(3) . ?
C8 C9 1.380(3) . ?
C9 C10 1.385(3) . ?
C10 C11 1.384(4) . ?
C11 C12 1.388(4) . ?
C12 N4 1.334(3) . ?
N2 N3 1.362(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
Cl1 Hg1 Cl2 132.52(3) . . ?
Cl1 Hg1 N1 109.77(5) . . ?
Cl2 Hg1 N1 98.30(5) . . ?
Cl1 Hg1 N2 106.60(5) . . ?
Cl2 Hg1 N2 119.75(5) . . ?
N1 Hg1 N2 66.17(6) . . ?
N1 C1 C2 122.8(2) . . ?
C3 C2 C1 118.1(2) . . ?
C2 C3 C4 119.4(2) . . ?
C3 C4 C5 119.5(2) . . ?
N1 C5 C4 121.1(2) . . ?
N1 C5 C6 116.49(18) . . ?
C4 C5 C6 122.4(2) . . ?
N2 C6 C5 115.63(19) . . ?
N2 C6 C13 123.8(2) . . ?
C5 C6 C13 120.54(19) . . ?
O1 C7 N3 124.1(2) . . ?
O1 C7 C8 123.8(2) . . ?
N3 C7 C8 112.14(19) . . ?
N4 C8 C9 123.4(2) . . ?
N4 C8 C7 115.1(2) . . ?
C9 C8 C7 121.5(2) . . ?
C8 C9 C10 118.6(2) . . ?
C11 C10 C9 118.7(2) . . ?
C10 C11 C12 118.6(2) . . ?
N4 C12 C11 123.2(2) . . ?
C1 N1 C5 119.1(2) . . ?
C1 N1 Hg1 121.69(16) . . ?
C5 N1 Hg1 119.21(14) . . ?
C6 N2 N3 119.05(18) . . ?
C6 N2 Hg1 120.97(14) . . ?
N3 N2 Hg1 119.41(13) . . ?
C7 N3 N2 120.30(18) . . ?
C12 N4 C8 117.4(2) . . ?

_refine_diff_density_max         1.045
_refine_diff_density_min         -1.868
_refine_diff_density_rms         0.136

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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 1506199'
_audit_update_record             
;
2016-09-24 deposited with the CCDC.
2016-10-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H12 Br2 Hg N4 O'
_chemical_formula_weight         600.68

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'
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'
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                   8.1943(2)
_cell_length_b                   13.4627(2)
_cell_length_c                   14.4493(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.865(2)
_cell_angle_gamma                90
_cell_volume                     1593.83(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    190(2)
_cell_measurement_reflns_used    4945
_cell_measurement_theta_min      2.8337
_cell_measurement_theta_max      32.0910

_exptl_crystal_description       Prismatic
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.503
_exptl_crystal_F_000             1104
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    14.674
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.31371
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      190(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12855
_diffrn_reflns_av_unetI/netI     0.0535
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.839
_diffrn_reflns_theta_max         32.164
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.922
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.922
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.922
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5179
_reflns_number_gt                3940
_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 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (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)+(0.0227P)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
_refine_ls_extinction_coef       0.00100(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5179
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0586
_refine_ls_R_factor_gt           0.0368
_refine_ls_wR_factor_ref         0.0728
_refine_ls_wR_factor_gt          0.0638
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_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 0.31151(2) 0.18866(2) 0.21245(2) 0.03140(7) Uani 1 1 d . . . . .
Br1 Br 0.44179(6) 0.34820(4) 0.26248(4) 0.03705(13) Uani 1 1 d . . . . .
Br2 Br 0.03760(6) 0.14778(4) 0.14678(4) 0.04012(13) Uani 1 1 d . . . . .
C1 C 0.5636(6) 0.1904(3) 0.0346(3) 0.0332(11) Uani 1 1 d . . . . .
H1 H 0.5154 0.2525 0.0273 0.040 Uiso 1 1 calc R U . . .
C2 C 0.6808(6) 0.1614(4) -0.0283(3) 0.0356(12) Uani 1 1 d . . . . .
H2 H 0.7117 0.2032 -0.0762 0.043 Uiso 1 1 calc R U . . .
C3 C 0.7496(6) 0.0692(4) -0.0175(3) 0.0328(11) Uani 1 1 d . . . . .
H3 H 0.8272 0.0469 -0.0590 0.039 Uiso 1 1 calc R U . . .
C4 C 0.7030(6) 0.0095(4) 0.0553(3) 0.0326(11) Uani 1 1 d . . . . .
H4 H 0.7484 -0.0533 0.0633 0.039 Uiso 1 1 calc R U . . .
C5 C 0.5873(5) 0.0448(3) 0.1163(3) 0.0267(10) Uani 1 1 d . . . . .
C6 C 0.5372(5) -0.0137(3) 0.1988(3) 0.0259(9) Uani 1 1 d . . . . .
C7 C 0.3041(5) 0.0338(3) 0.3966(3) 0.0268(9) Uani 1 1 d . . . . .
C8 C 0.2797(5) -0.0275(3) 0.4825(3) 0.0260(9) Uani 1 1 d . . . . .
C9 C 0.1824(6) 0.0079(4) 0.5526(3) 0.0334(11) Uani 1 1 d . . . . .
H9 H 0.1307 0.0692 0.5479 0.040 Uiso 1 1 calc R U . . .
C10 C 0.1647(6) -0.0518(4) 0.6305(3) 0.0331(11) Uani 1 1 d . . . . .
H10 H 0.0990 -0.0314 0.6788 0.040 Uiso 1 1 calc R U . . .
C11 C 0.2456(6) -0.1414(3) 0.6351(4) 0.0362(12) Uani 1 1 d . . . . .
H11 H 0.2367 -0.1821 0.6868 0.043 Uiso 1 1 calc R U . . .
C12 C 0.3403(7) -0.1694(3) 0.5611(4) 0.0380(12) Uani 1 1 d . . . . .
H12 H 0.3950 -0.2298 0.5643 0.046 Uiso 1 1 calc R U . . .
C13 C 0.5982(6) -0.1170(3) 0.2143(3) 0.0348(11) Uani 1 1 d . . . . .
H13A H 0.6879 -0.1157 0.2578 0.052 Uiso 1 1 d R U . . .
H13B H 0.6339 -0.1444 0.1567 0.052 Uiso 1 1 d R U . . .
H13C H 0.5119 -0.1571 0.2384 0.052 Uiso 1 1 d R U . . .
N1 N 0.5168(5) 0.1339(3) 0.1047(3) 0.0272(8) Uani 1 1 d . . . . .
N2 N 0.4435(4) 0.0330(3) 0.2557(2) 0.0252(8) Uani 1 1 d . . . . .
N3 N 0.4025(5) -0.0132(3) 0.3360(2) 0.0276(8) Uani 1 1 d . . . . .
H3A H 0.4388 -0.0718 0.3481 0.033 Uiso 1 1 calc R U . . .
N4 N 0.3570(5) -0.1136(3) 0.4854(3) 0.0330(9) Uani 1 1 d . . . . .
O1 O 0.2439(4) 0.1150(2) 0.3836(2) 0.0350(8) 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
Hg1 N1 2.424(3) . ?
Hg1 N2 2.435(4) . ?
Hg1 Br2 2.4854(6) . ?
Hg1 Br1 2.5004(5) . ?
C1 N1 1.328(5) . ?
C1 C2 1.388(6) . ?
C1 H1 0.9300 . ?
C2 C3 1.372(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.382(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.389(6) . ?
C4 H4 0.9300 . ?
C5 N1 1.340(6) . ?
C5 C6 1.491(6) . ?
C6 N2 1.296(5) . ?
C6 C13 1.493(6) . ?
C7 O1 1.213(5) . ?
C7 N3 1.356(5) . ?
C7 C8 1.507(6) . ?
C8 N4 1.321(6) . ?
C8 C9 1.383(6) . ?
C9 C10 1.391(6) . ?
C9 H9 0.9300 . ?
C10 C11 1.377(7) . ?
C10 H10 0.9300 . ?
C11 C12 1.383(7) . ?
C11 H11 0.9300 . ?
C12 N4 1.336(6) . ?
C12 H12 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
N2 N3 1.363(5) . ?
N3 H3A 0.8600 . ?

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 N2 65.99(12) . . ?
N1 Hg1 Br2 108.60(10) . . ?
N2 Hg1 Br2 107.60(9) . . ?
N1 Hg1 Br1 98.60(9) . . ?
N2 Hg1 Br1 118.62(9) . . ?
Br2 Hg1 Br1 132.828(19) . . ?
N1 C1 C2 123.2(4) . . ?
N1 C1 H1 118.4 . . ?
C2 C1 H1 118.4 . . ?
C3 C2 C1 117.9(4) . . ?
C3 C2 H2 121.1 . . ?
C1 C2 H2 121.1 . . ?
C2 C3 C4 119.7(4) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C3 C4 C5 118.9(5) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 H4 120.6 . . ?
N1 C5 C4 121.6(4) . . ?
N1 C5 C6 116.7(4) . . ?
C4 C5 C6 121.7(4) . . ?
N2 C6 C5 115.0(4) . . ?
N2 C6 C13 123.8(4) . . ?
C5 C6 C13 121.1(4) . . ?
O1 C7 N3 124.4(4) . . ?
O1 C7 C8 124.2(4) . . ?
N3 C7 C8 111.4(4) . . ?
N4 C8 C9 124.1(4) . . ?
N4 C8 C7 115.9(4) . . ?
C9 C8 C7 120.0(4) . . ?
C8 C9 C10 117.4(4) . . ?
C8 C9 H9 121.3 . . ?
C10 C9 H9 121.3 . . ?
C11 C10 C9 119.3(4) . . ?
C11 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
C10 C11 C12 118.4(5) . . ?
C10 C11 H11 120.8 . . ?
C12 C11 H11 120.8 . . ?
N4 C12 C11 123.1(5) . . ?
N4 C12 H12 118.5 . . ?
C11 C12 H12 118.5 . . ?
C6 C13 H13A 109.5 . . ?
C6 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C6 C13 H13C 109.4 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C1 N1 C5 118.7(4) . . ?
C1 N1 Hg1 121.7(3) . . ?
C5 N1 Hg1 119.6(3) . . ?
C6 N2 N3 118.3(4) . . ?
C6 N2 Hg1 121.3(3) . . ?
N3 N2 Hg1 119.8(3) . . ?
C7 N3 N2 119.5(4) . . ?
C7 N3 H3A 120.2 . . ?
N2 N3 H3A 120.2 . . ?
C8 N4 C12 117.6(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 0.8(8) . . . . ?
C1 C2 C3 C4 -1.1(8) . . . . ?
C2 C3 C4 C5 -0.2(7) . . . . ?
C3 C4 C5 N1 2.0(7) . . . . ?
C3 C4 C5 C6 -177.1(4) . . . . ?
N1 C5 C6 N2 -7.1(6) . . . . ?
C4 C5 C6 N2 172.0(4) . . . . ?
N1 C5 C6 C13 175.2(4) . . . . ?
C4 C5 C6 C13 -5.7(7) . . . . ?
O1 C7 C8 N4 -178.9(5) . . . . ?
N3 C7 C8 N4 0.8(6) . . . . ?
O1 C7 C8 C9 0.5(7) . . . . ?
N3 C7 C8 C9 -179.8(4) . . . . ?
N4 C8 C9 C10 -0.5(8) . . . . ?
C7 C8 C9 C10 -179.8(4) . . . . ?
C8 C9 C10 C11 1.0(7) . . . . ?
C9 C10 C11 C12 -0.8(8) . . . . ?
C10 C11 C12 N4 0.0(8) . . . . ?
C2 C1 N1 C5 0.8(8) . . . . ?
C2 C1 N1 Hg1 179.9(4) . . . . ?
C4 C5 N1 C1 -2.2(7) . . . . ?
C6 C5 N1 C1 176.9(4) . . . . ?
C4 C5 N1 Hg1 178.6(3) . . . . ?
C6 C5 N1 Hg1 -2.2(5) . . . . ?
C5 C6 N2 N3 -175.3(4) . . . . ?
C13 C6 N2 N3 2.4(7) . . . . ?
C5 C6 N2 Hg1 13.4(5) . . . . ?
C13 C6 N2 Hg1 -169.0(3) . . . . ?
O1 C7 N3 N2 2.3(7) . . . . ?
C8 C7 N3 N2 -177.4(4) . . . . ?
C6 N2 N3 C7 -179.7(4) . . . . ?
Hg1 N2 N3 C7 -8.2(5) . . . . ?
C9 C8 N4 C12 -0.3(8) . . . . ?
C7 C8 N4 C12 179.0(4) . . . . ?
C11 C12 N4 C8 0.6(8) . . . . ?

_refine_diff_density_max         1.827
_refine_diff_density_min         -1.969
_refine_diff_density_rms         0.181

_shelxl_version_number           2014-3

