# Electronic Supplementary Material (ESI) for Dalton Transactions.
# 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_d
_database_code_depnum_ccdc_archive 'CCDC 1062554'
_audit_update_record             
;
2016-03-29 deposited with the CCDC.
2016-06-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H11 Cl1 Hg1 I2 N2'
_chemical_formula_weight         721.11

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'
I I -0.4742 1.8119 '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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P21nb

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, y+1/2, -z+1/2'
'x+1/2, -y, -z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   7.4201(5)
_cell_length_b                   8.7404(5)
_cell_length_c                   28.185(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1827.9(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    8298
_cell_measurement_theta_min      1.44
_cell_measurement_theta_max      27.00

_exptl_crystal_description       Plate
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.620
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1296
_exptl_absorpt_coefficient_mu    11.941
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.3021
_exptl_absorpt_correction_T_max  0.6001
_exptl_absorpt_process_details   'shape of crystal determined optically'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      298(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  'STOE IPDS II'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean '0.15 mm'
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8298
_diffrn_reflns_av_R_equivalents  0.1099
_diffrn_reflns_av_sigmaI/netI    0.0860
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_theta_min         1.44
_diffrn_reflns_theta_max         27.00
_reflns_number_total             3174
_reflns_number_gt                2181
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_cell_refinement       'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_data_reduction        'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1051P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.007(16)
_refine_ls_number_reflns         3174
_refine_ls_number_parameters     199
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0827
_refine_ls_R_factor_gt           0.0631
_refine_ls_wR_factor_ref         0.1722
_refine_ls_wR_factor_gt          0.1637
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.011
_refine_ls_shift/su_max          0.005
_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
Hg1 Hg 0.49326(9) 0.83402(10) 0.25507(2) 0.0548(3) Uani 1 1 d . . .
I2 I 0.25669(18) 1.07491(14) 0.25759(5) 0.0504(4) Uani 1 1 d . . .
I1 I 0.7898(3) 0.7978(2) 0.20387(7) 0.0741(5) Uani 1 1 d . . .
N1 N 0.545(2) 0.8094(19) 0.3381(7) 0.049(4) Uani 1 1 d . . .
C4 C 0.551(3) 0.933(2) 0.3675(7) 0.046(5) Uani 1 1 d . . .
H4 H 0.5229 1.0290 0.3552 0.056 Uiso 1 1 calc R . .
C1 C 0.635(3) 0.777(3) 0.4330(7) 0.047(5) Uani 1 1 d . . .
H1 H 0.6667 0.7667 0.4648 0.056 Uiso 1 1 calc R . .
C5 C 0.596(3) 0.923(3) 0.4128(8) 0.047(5) Uani 1 1 d . . .
C3 C 0.575(3) 0.670(3) 0.3549(9) 0.058(6) Uani 1 1 d . . .
H3 H 0.5631 0.5852 0.3353 0.069 Uiso 1 1 calc R . .
C6 C 0.616(3) 1.061(3) 0.4441(7) 0.050(5) Uani 1 1 d . . .
H6A H 0.5733 1.1541 0.4324 0.060 Uiso 1 1 calc R . .
N2 N 0.681(2) 1.062(2) 0.4819(6) 0.050(4) Uani 1 1 d . . .
C7 C 0.696(3) 1.202(3) 0.5065(9) 0.053(5) Uani 1 1 d . . .
C2 C 0.625(3) 0.653(3) 0.4033(9) 0.053(5) Uani 1 1 d . . .
H2 H 0.6502 0.5560 0.4151 0.064 Uiso 1 1 calc R . .
C8 C 0.772(3) 1.332(2) 0.4889(8) 0.054(5) Uani 1 1 d . . .
H8 H 0.8150 1.3296 0.4580 0.065 Uiso 1 1 calc R . .
C9 C 0.789(4) 1.464(3) 0.5127(9) 0.060(6) Uani 1 1 d . . .
H9 H 0.8456 1.5475 0.4988 0.072 Uiso 1 1 calc R . .
C16 C 0.640(3) 1.203(3) 0.5552(7) 0.047(5) Uani 1 1 d . . .
C15 C 0.581(3) 1.071(3) 0.5780(8) 0.055(6) Uani 1 1 d . . .
H15 H 0.5764 0.9801 0.5612 0.066 Uiso 1 1 calc R . .
C11 C 0.649(3) 1.342(3) 0.5823(8) 0.056(6) Uani 1 1 d . . .
C10 C 0.719(3) 1.474(2) 0.5591(9) 0.060(6) Uani 1 1 d . . .
Cl1 Cl 0.7349(13) 1.6429(8) 0.5892(3) 0.095(2) Uani 1 1 d . . .
C14 C 0.530(3) 1.073(3) 0.6250(8) 0.065(7) Uani 1 1 d . . .
H14 H 0.4901 0.9838 0.6396 0.078 Uiso 1 1 calc R . .
C13 C 0.537(3) 1.208(4) 0.6500(8) 0.076(9) Uani 1 1 d . . .
H13 H 0.5067 1.2093 0.6819 0.091 Uiso 1 1 calc R . .
C12 C 0.590(3) 1.340(3) 0.6283(9) 0.059(6) Uani 1 1 d . . .
H12 H 0.5853 1.4313 0.6453 0.070 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Hg1 N1 2.38(2) . ?
Hg1 I1 2.650(2) . ?
Hg1 I2 2.7421(14) . ?
Hg1 I2 2.8876(16) 2_545 ?
I2 Hg1 2.8875(16) 2 ?
N1 C3 1.32(3) . ?
N1 C4 1.37(3) . ?
C4 C5 1.32(3) . ?
C4 H4 0.9300 . ?
C1 C2 1.37(3) . ?
C1 C5 1.43(3) . ?
C1 H1 0.9300 . ?
C5 C6 1.50(3) . ?
C3 C2 1.42(3) . ?
C3 H3 0.9300 . ?
C6 N2 1.17(3) . ?
C6 H6A 0.9300 . ?
N2 C7 1.41(3) . ?
C7 C8 1.36(3) . ?
C7 C16 1.44(3) . ?
C2 H2 0.9300 . ?
C8 C9 1.34(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.41(3) . ?
C9 H9 0.9300 . ?
C16 C15 1.39(3) . ?
C16 C11 1.44(3) . ?
C15 C14 1.38(3) . ?
C15 H15 0.9300 . ?
C11 C12 1.37(3) . ?
C11 C10 1.42(3) . ?
C10 Cl1 1.71(2) . ?
C14 C13 1.38(4) . ?
C14 H14 0.9300 . ?
C13 C12 1.36(4) . ?
C13 H13 0.9300 . ?
C12 H12 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Hg1 I1 112.9(4) . . ?
N1 Hg1 I2 98.5(4) . . ?
I1 Hg1 I2 129.60(6) . . ?
N1 Hg1 I2 98.6(4) . 2_545 ?
I1 Hg1 I2 110.10(5) . 2_545 ?
I2 Hg1 I2 102.49(5) . 2_545 ?
Hg1 I2 Hg1 102.11(5) . 2 ?
C3 N1 C4 120(2) . . ?
C3 N1 Hg1 117.5(16) . . ?
C4 N1 Hg1 122.0(13) . . ?
C5 C4 N1 123(2) . . ?
C5 C4 H4 118.6 . . ?
N1 C4 H4 118.6 . . ?
C2 C1 C5 116.8(19) . . ?
C2 C1 H1 121.6 . . ?
C5 C1 H1 121.6 . . ?
C4 C5 C1 120(2) . . ?
C4 C5 C6 122(2) . . ?
C1 C5 C6 117.7(19) . . ?
N1 C3 C2 119(2) . . ?
N1 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
N2 C6 C5 125(2) . . ?
N2 C6 H6A 117.4 . . ?
C5 C6 H6A 117.4 . . ?
C6 N2 C7 118.8(19) . . ?
C8 C7 N2 126(2) . . ?
C8 C7 C16 118(2) . . ?
N2 C7 C16 117(2) . . ?
C1 C2 C3 121(2) . . ?
C1 C2 H2 119.4 . . ?
C3 C2 H2 119.4 . . ?
C9 C8 C7 125(2) . . ?
C9 C8 H8 117.4 . . ?
C7 C8 H8 117.4 . . ?
C8 C9 C10 119(2) . . ?
C8 C9 H9 120.5 . . ?
C10 C9 H9 120.5 . . ?
C15 C16 C7 122(2) . . ?
C15 C16 C11 118(2) . . ?
C7 C16 C11 120(2) . . ?
C14 C15 C16 122(2) . . ?
C14 C15 H15 119.2 . . ?
C16 C15 H15 119.2 . . ?
C12 C11 C10 124(2) . . ?
C12 C11 C16 119(2) . . ?
C10 C11 C16 117(2) . . ?
C9 C10 C11 121(2) . . ?
C9 C10 Cl1 119.3(19) . . ?
C11 C10 Cl1 120(2) . . ?
C13 C14 C15 119(3) . . ?
C13 C14 H14 120.4 . . ?
C15 C14 H14 120.4 . . ?
C12 C13 C14 121(2) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C13 C12 C11 122(2) . . ?
C13 C12 H12 119.1 . . ?
C11 C12 H12 119.1 . . ?

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 Hg1 I2 Hg1 93.7(4) . . . 2 ?
I1 Hg1 I2 Hg1 -35.68(9) . . . 2 ?
I2 Hg1 I2 Hg1 -165.47(6) 2_545 . . 2 ?
I1 Hg1 N1 C3 -73.5(15) . . . . ?
I2 Hg1 N1 C3 146.8(15) . . . . ?
I2 Hg1 N1 C3 42.7(15) 2_545 . . . ?
I1 Hg1 N1 C4 104.3(15) . . . . ?
I2 Hg1 N1 C4 -35.5(15) . . . . ?
I2 Hg1 N1 C4 -139.6(15) 2_545 . . . ?
C3 N1 C4 C5 4(3) . . . . ?
Hg1 N1 C4 C5 -173.8(16) . . . . ?
N1 C4 C5 C1 -2(3) . . . . ?
N1 C4 C5 C6 175(2) . . . . ?
C2 C1 C5 C4 0(3) . . . . ?
C2 C1 C5 C6 -177(2) . . . . ?
C4 N1 C3 C2 -4(3) . . . . ?
Hg1 N1 C3 C2 173.6(16) . . . . ?
C4 C5 C6 N2 -168(2) . . . . ?
C1 C5 C6 N2 9(3) . . . . ?
C5 C6 N2 C7 178(2) . . . . ?
C6 N2 C7 C8 -52(3) . . . . ?
C6 N2 C7 C16 133(2) . . . . ?
C5 C1 C2 C3 -1(3) . . . . ?
N1 C3 C2 C1 3(4) . . . . ?
N2 C7 C8 C9 -179(2) . . . . ?
C16 C7 C8 C9 -4(3) . . . . ?
C7 C8 C9 C10 -2(4) . . . . ?
C8 C7 C16 C15 -172.5(19) . . . . ?
N2 C7 C16 C15 3(3) . . . . ?
C8 C7 C16 C11 6(3) . . . . ?
N2 C7 C16 C11 -179.0(17) . . . . ?
C7 C16 C15 C14 179(2) . . . . ?
C11 C16 C15 C14 1(3) . . . . ?
C15 C16 C11 C12 -3(3) . . . . ?
C7 C16 C11 C12 178(2) . . . . ?
C15 C16 C11 C10 177(2) . . . . ?
C7 C16 C11 C10 -2(3) . . . . ?
C8 C9 C10 C11 7(4) . . . . ?
C8 C9 C10 Cl1 -178.3(19) . . . . ?
C12 C11 C10 C9 176(2) . . . . ?
C16 C11 C10 C9 -5(3) . . . . ?
C12 C11 C10 Cl1 1(3) . . . . ?
C16 C11 C10 Cl1 -179.6(15) . . . . ?
C16 C15 C14 C13 0(3) . . . . ?
C15 C14 C13 C12 2(4) . . . . ?
C14 C13 C12 C11 -5(4) . . . . ?
C10 C11 C12 C13 -175(2) . . . . ?
C16 C11 C12 C13 5(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         1.210
_refine_diff_density_min         -2.310
_refine_diff_density_rms         0.386
####################################################################### 
# 
# 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_d
_database_code_depnum_ccdc_archive 'CCDC 1062555'
_audit_update_record             
;
2016-03-29 deposited with the CCDC.
2016-06-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H22 Br2 Cl2 Hg1 N4 O2'
_chemical_formula_weight         925.83

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Hg Hg -2.3894 9.2266 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   26.837(5)
_cell_length_b                   4.7735(8)
_cell_length_c                   25.763(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 112.327(14)
_cell_angle_gamma                90.00
_cell_volume                     3052.9(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    13131
_cell_measurement_theta_min      2.78
_cell_measurement_theta_max      27.00

_exptl_crystal_description       Needle
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.050
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.014
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1768
_exptl_absorpt_coefficient_mu    7.872
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.3633
_exptl_absorpt_correction_T_max  0.4509
_exptl_absorpt_process_details   'shape of crystal determined optically'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      298(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  'STOE IPDS II'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean '0.15 mm'
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13131
_diffrn_reflns_av_R_equivalents  0.0917
_diffrn_reflns_av_sigmaI/netI    0.0818
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         2.78
_diffrn_reflns_theta_max         27.00
_reflns_number_total             3317
_reflns_number_gt                1894
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_cell_refinement       'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_data_reduction        'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0847P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3317
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0711
_refine_ls_R_factor_gt           0.0512
_refine_ls_wR_factor_ref         0.1312
_refine_ls_wR_factor_gt          0.1112
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.015
_refine_ls_shift/su_mean         0.003

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.0647(7) -0.405(4) 0.4120(9) 0.051(5) Uani 1 1 d . . .
H1 H 0.0770 -0.5435 0.4393 0.062 Uiso 1 1 calc R . .
C2 C 0.0139(7) -0.318(5) 0.3948(8) 0.047(5) Uani 1 1 d . . .
H2 H -0.0093 -0.3867 0.4109 0.064 Uiso 1 1 calc R . .
C3 C -0.0036(7) -0.118(4) 0.3511(7) 0.046(5) Uani 1 1 d . . .
H3 H -0.0392 -0.0566 0.3383 0.055 Uiso 1 1 calc R . .
C4 C 0.0802(6) -0.100(3) 0.3464(6) 0.050(4) Uiso 1 1 d . . .
H4 H 0.1036 -0.0321 0.3304 0.038 Uiso 1 1 calc R . .
C5 C 0.0997(6) -0.289(4) 0.3893(7) 0.044(5) Uani 1 1 d . . .
C6 C 0.1582(6) -0.401(3) 0.4057(7) 0.042(4) Uani 1 1 d . . .
C7 C 0.2476(7) -0.253(3) 0.4167(8) 0.048(5) Uani 1 1 d . . .
C8 C 0.2774(7) -0.435(4) 0.4569(7) 0.042(4) Uani 1 1 d . . .
H8 H 0.2628 -0.5274 0.4796 0.051 Uiso 1 1 calc R . .
C9 C 0.3334(8) -0.479(4) 0.4633(10) 0.046(7) Uani 1 1 d . . .
H9A H 0.3534 -0.6185 0.4875 0.076 Uiso 1 1 calc R . .
C10 C 0.3552(7) -0.333(5) 0.4368(8) 0.047(4) Uani 1 1 d . . .
C11 C 0.3263(6) -0.140(3) 0.3925(9) 0.050(5) Uani 1 1 d . . .
C12 C 0.3483(8) 0.007(5) 0.3590(8) 0.056(5) Uani 1 1 d . . .
H12 H 0.3845 -0.0169 0.3650 0.067 Uiso 1 1 calc R . .
C13 C 0.3181(8) 0.181(5) 0.3187(9) 0.062(5) Uani 1 1 d . . .
H13 H 0.3334 0.2728 0.2965 0.075 Uiso 1 1 calc R . .
C14 C 0.2648(9) 0.227(4) 0.3095(9) 0.058(5) Uani 1 1 d . . .
H14 H 0.2452 0.3583 0.2828 0.069 Uiso 1 1 calc R . .
C15 C 0.2404(8) 0.082(4) 0.3392(9) 0.061(7) Uani 1 1 d . . .
H15 H 0.2037 0.1050 0.3304 0.074 Uiso 1 1 calc R . .
C16 C 0.2704(6) -0.104(3) 0.3834(6) 0.048(3) Uani 1 1 d . . .
N1 N 0.0300(5) -0.009(3) 0.3265(6) 0.046(4) Uani 1 1 d . . .
N2 N 0.1928(5) -0.210(3) 0.4060(5) 0.045(3) Uani 1 1 d . . .
H2A H 0.1810 -0.0409 0.3989 0.037 Uiso 1 1 calc R . .
O1 O 0.1681(5) -0.641(2) 0.4210(6) 0.055(4) Uani 1 1 d . . .
Br1 Br 0.43049(8) -0.3969(5) 0.45088(10) 0.0721(8) Uani 1 1 d . . .
Hg1 Hg 0.0000 0.3212(2) 0.2500 0.0437(4) Uani 1 2 d S . .
Cl1 Cl 0.0859(2) 0.4167(11) 0.2508(2) 0.0641(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
C1 C2 1.33(2) . ?
C1 C5 1.40(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.42(3) . ?
C2 H2 0.9300 . ?
C3 N1 1.38(2) . ?
C3 H3 0.9300 . ?
C4 N1 1.321(19) . ?
C4 C5 1.37(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.56(2) . ?
C6 O1 1.209(17) . ?
C6 N2 1.30(2) . ?
C7 C8 1.36(2) . ?
C7 N2 1.40(2) . ?
C7 C16 1.42(2) . ?
C8 C9 1.46(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.27(3) . ?
C9 H9A 0.9300 . ?
C10 C11 1.44(3) . ?
C10 Br1 1.936(17) . ?
C11 C12 1.41(3) . ?
C11 C16 1.44(2) . ?
C12 C13 1.34(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.38(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.37(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.43(2) . ?
C15 H15 0.9300 . ?
N1 Hg1 2.412(16) . ?
N2 H2A 0.8600 . ?
Hg1 Cl1 2.342(5) 2 ?
Hg1 Cl1 2.342(5) . ?
Hg1 N1 2.412(16) 2 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C5 120.2(18) . . ?
C2 C1 H1 119.9 . . ?
C5 C1 H1 119.9 . . ?
C1 C2 C3 117.8(18) . . ?
C1 C2 H2 121.1 . . ?
C3 C2 H2 121.1 . . ?
N1 C3 C2 122.6(16) . . ?
N1 C3 H3 118.7 . . ?
C2 C3 H3 118.7 . . ?
N1 C4 C5 123.3(17) . . ?
N1 C4 H4 118.3 . . ?
C5 C4 H4 118.3 . . ?
C4 C5 C1 119.3(15) . . ?
C4 C5 C6 118.7(17) . . ?
C1 C5 C6 121.4(16) . . ?
O1 C6 N2 126.6(14) . . ?
O1 C6 C5 119.1(15) . . ?
N2 C6 C5 114.0(13) . . ?
C8 C7 N2 120.9(19) . . ?
C8 C7 C16 121.1(17) . . ?
N2 C7 C16 117.9(13) . . ?
C7 C8 C9 117.5(19) . . ?
C7 C8 H8 121.2 . . ?
C9 C8 H8 121.2 . . ?
C10 C9 C8 121.6(18) . . ?
C10 C9 H9A 119.2 . . ?
C8 C9 H9A 119.2 . . ?
C9 C10 C11 124.0(17) . . ?
C9 C10 Br1 118.4(16) . . ?
C11 C10 Br1 117.3(15) . . ?
C12 C11 C16 119.8(16) . . ?
C12 C11 C10 125.4(17) . . ?
C16 C11 C10 114.8(18) . . ?
C13 C12 C11 121(2) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C12 C13 C14 121(2) . . ?
C12 C13 H13 119.4 . . ?
C14 C13 H13 119.4 . . ?
C15 C14 C13 121(2) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C14 C15 C16 121.1(19) . . ?
C14 C15 H15 119.5 . . ?
C16 C15 H15 119.5 . . ?
C7 C16 C15 123.4(16) . . ?
C7 C16 C11 120.4(14) . . ?
C15 C16 C11 116.2(17) . . ?
C4 N1 C3 116.5(15) . . ?
C4 N1 Hg1 120.4(12) . . ?
C3 N1 Hg1 123.1(11) . . ?
C6 N2 C7 126.3(13) . . ?
C6 N2 H2A 116.9 . . ?
C7 N2 H2A 116.9 . . ?
Cl1 Hg1 Cl1 157.5(3) 2 . ?
Cl1 Hg1 N1 95.7(4) 2 2 ?
Cl1 Hg1 N1 99.0(4) . 2 ?
Cl1 Hg1 N1 99.0(4) 2 . ?
Cl1 Hg1 N1 95.7(4) . . ?
N1 Hg1 N1 98.3(7) 2 . ?

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
C5 C1 C2 C3 3(3) . . . . ?
C1 C2 C3 N1 -1(3) . . . . ?
N1 C4 C5 C1 3(3) . . . . ?
N1 C4 C5 C6 174.7(14) . . . . ?
C2 C1 C5 C4 -5(3) . . . . ?
C2 C1 C5 C6 -175.8(16) . . . . ?
C4 C5 C6 O1 -144.7(18) . . . . ?
C1 C5 C6 O1 27(3) . . . . ?
C4 C5 C6 N2 41(2) . . . . ?
C1 C5 C6 N2 -147.4(17) . . . . ?
N2 C7 C8 C9 176.7(15) . . . . ?
C16 C7 C8 C9 -2(2) . . . . ?
C7 C8 C9 C10 8(3) . . . . ?
C8 C9 C10 C11 -9(3) . . . . ?
C8 C9 C10 Br1 177.2(14) . . . . ?
C9 C10 C11 C12 -174(2) . . . . ?
Br1 C10 C11 C12 -1(3) . . . . ?
C9 C10 C11 C16 6(3) . . . . ?
Br1 C10 C11 C16 179.1(12) . . . . ?
C16 C11 C12 C13 0(3) . . . . ?
C10 C11 C12 C13 179.9(19) . . . . ?
C11 C12 C13 C14 2(3) . . . . ?
C12 C13 C14 C15 -4(3) . . . . ?
C13 C14 C15 C16 5(3) . . . . ?
C8 C7 C16 C15 177.8(16) . . . . ?
N2 C7 C16 C15 -1(2) . . . . ?
C8 C7 C16 C11 -1(2) . . . . ?
N2 C7 C16 C11 -180.0(14) . . . . ?
C14 C15 C16 C7 177.9(17) . . . . ?
C14 C15 C16 C11 -3(3) . . . . ?
C12 C11 C16 C7 179.7(16) . . . . ?
C10 C11 C16 C7 0(2) . . . . ?
C12 C11 C16 C15 1(2) . . . . ?
C10 C11 C16 C15 -179.1(15) . . . . ?
C5 C4 N1 C3 -1(2) . . . . ?
C5 C4 N1 Hg1 -179.4(12) . . . . ?
C2 C3 N1 C4 -1(2) . . . . ?
C2 C3 N1 Hg1 178.0(13) . . . . ?
O1 C6 N2 C7 10(3) . . . . ?
C5 C6 N2 C7 -177.0(15) . . . . ?
C8 C7 N2 C6 -39(2) . . . . ?
C16 C7 N2 C6 139.6(16) . . . . ?
C4 N1 Hg1 Cl1 -172.7(11) . . . 2 ?
C3 N1 Hg1 Cl1 8.7(13) . . . 2 ?
C4 N1 Hg1 Cl1 -9.8(12) . . . . ?
C3 N1 Hg1 Cl1 171.7(13) . . . . ?
C4 N1 Hg1 N1 90.2(13) . . . 2 ?
C3 N1 Hg1 N1 -88.4(13) . . . 2 ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         1.153
_refine_diff_density_min         -1.147
_refine_diff_density_rms         0.259
####################################################################### 
# 
# 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_d:\determination\solution\c728\khc728-abs
_database_code_depnum_ccdc_archive 'CCDC 1062556'
_audit_update_record             
;
2015-04-30 deposited with the CCDC.
2016-06-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H11 Br1 Hg1 I2 N2'
_chemical_formula_weight         765.56

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'
I I -0.4742 1.8119 '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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P21nb

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, y+1/2, -z+1/2'
'x+1/2, -y, -z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   7.4259(6)
_cell_length_b                   8.8140(10)
_cell_length_c                   28.085(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1838.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    17533
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      27.00

_exptl_crystal_description       Needle
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.766
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1368
_exptl_absorpt_coefficient_mu    13.903
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.3109
_exptl_absorpt_correction_T_max  0.5961
_exptl_absorpt_process_details   'shape of crystal determined optically'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      298(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  'STOE IPDS II'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean '0.15 mm'
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            17533
_diffrn_reflns_av_R_equivalents  0.0883
_diffrn_reflns_av_sigmaI/netI    0.0991
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         2.42
_diffrn_reflns_theta_max         27.00
_reflns_number_total             4010
_reflns_number_gt                3860
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_cell_refinement       'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_data_reduction        'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0259P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.028(16)
_refine_ls_number_reflns         4010
_refine_ls_number_parameters     184
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0912
_refine_ls_R_factor_gt           0.0863
_refine_ls_wR_factor_ref         0.1313
_refine_ls_wR_factor_gt          0.1086
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.011
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.003

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.442(4) -0.281(3) -0.5680(10) 0.050(8) Uani 1 1 d . . .
H1 H -0.4754 -0.2709 -0.5363 0.060 Uiso 1 1 calc R . .
C2 C -0.430(4) -0.155(4) -0.5972(8) 0.046(7) Uani 1 1 d . . .
H2 H -0.4510 -0.0587 -0.5851 0.055 Uiso 1 1 calc R . .
C3 C -0.388(3) -0.174(3) -0.6436(8) 0.040(6) Uani 1 1 d . . .
H3 H -0.3881 -0.0897 -0.6634 0.048 Uiso 1 1 calc R . .
C4 C -0.355(4) -0.433(3) -0.6348(9) 0.049(8) Uani 1 1 d . . .
H4 H -0.3295 -0.5269 -0.6482 0.059 Uiso 1 1 calc R . .
C5 C -0.400(4) -0.425(3) -0.5877(10) 0.045(7) Uani 1 1 d . . .
C6 C -0.426(4) -0.553(3) -0.5596(10) 0.042(8) Uani 1 1 d . . .
H6 H -0.3984 -0.6449 -0.5740 0.050 Uiso 1 1 calc R . .
C7 C -0.499(4) -0.704(3) -0.4911(9) 0.041(7) Uani 1 1 d . . .
C8 C -0.574(4) -0.835(4) -0.5103(8) 0.044(9) Uani 1 1 d . . .
H8 H -0.6163 -0.8348 -0.5414 0.082 Uiso 1 1 calc R . .
C9 C -0.585(5) -0.967(3) -0.4828(11) 0.047(10) Uani 1 1 d . . .
H9 H -0.6372 -1.0547 -0.4951 0.079 Uiso 1 1 calc R . .
C10 C -0.520(4) -0.965(3) -0.4378(9) 0.037(7) Uani 1 1 d . . .
C11 C -0.448(4) -0.838(3) -0.4162(8) 0.043(7) Uani 1 1 d . . .
C12 C -0.392(3) -0.834(4) -0.3682(8) 0.044(7) Uani 1 1 d . . .
H12 H -0.3906 -0.9223 -0.3502 0.053 Uiso 1 1 calc R . .
C13 C -0.340(3) -0.703(3) -0.3484(8) 0.048(8) Uani 1 1 d . . .
H13 H -0.3128 -0.7010 -0.3161 0.058 Uiso 1 1 calc R . .
C14 C -0.326(4) -0.569(3) -0.3750(10) 0.054(8) Uani 1 1 d . . .
H14 H -0.2767 -0.4823 -0.3612 0.064 Uiso 1 1 calc R . .
C15 C -0.384(3) -0.564(3) -0.4207(8) 0.050(7) Uani 1 1 d . . .
H15 H -0.3850 -0.4731 -0.4372 0.049 Uiso 1 1 calc R . .
C16 C -0.445(4) -0.699(3) -0.4434(10) 0.046(8) Uani 1 1 d . . .
N1 N -0.348(2) -0.308(2) -0.6624(7) 0.035(5) Uani 1 1 d . . .
N2 N -0.481(3) -0.561(2) -0.5177(7) 0.044(6) Uani 1 1 d . . .
Hg1 Hg -0.29678(14) -0.33686(12) -0.74513(3) 0.0537(3) Uani 1 1 d . . .
I1 I -0.5933(3) -0.3014(2) -0.79707(8) 0.0721(6) Uani 1 1 d . . .
I2 I -0.0624(2) -0.57745(19) -0.74163(6) 0.0495(5) Uani 1 1 d . . .
Br1 Br -0.5370(6) -1.1506(4) -0.40511(14) 0.0891(12) 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
C1 C2 1.38(4) . ?
C1 C5 1.42(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.35(3) . ?
C2 H2 0.9300 . ?
C3 N1 1.33(3) . ?
C3 H3 0.9300 . ?
C4 N1 1.34(3) . ?
C4 C5 1.37(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.39(3) . ?
C6 N2 1.25(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.39(3) . ?
C7 C16 1.40(4) . ?
C7 N2 1.48(3) . ?
C8 C9 1.40(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.35(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.38(4) . ?
C10 Br1 1.88(2) . ?
C11 C12 1.41(3) . ?
C11 C16 1.44(4) . ?
C12 C13 1.33(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.40(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.35(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.42(4) . ?
C15 H15 0.9300 . ?
N1 Hg1 2.369(19) . ?
Hg1 I1 2.660(2) . ?
Hg1 I2 2.745(2) . ?
Hg1 I2 2.897(2) 2_553 ?
I2 Hg1 2.897(2) 2_543 ?

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
C2 C1 C5 118(2) . . ?
C2 C1 H1 120.9 . . ?
C5 C1 H1 120.9 . . ?
C3 C2 C1 119(3) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
N1 C3 C2 123(2) . . ?
N1 C3 H3 118.4 . . ?
C2 C3 H3 118.4 . . ?
N1 C4 C5 122(3) . . ?
N1 C4 H4 119.2 . . ?
C5 C4 H4 119.2 . . ?
C4 C5 C6 123(3) . . ?
C4 C5 C1 119(3) . . ?
C6 C5 C1 118(2) . . ?
N2 C6 C5 129(3) . . ?
N2 C6 H6 115.6 . . ?
C5 C6 H6 115.6 . . ?
C8 C7 C16 121(2) . . ?
C8 C7 N2 123(2) . . ?
C16 C7 N2 116(2) . . ?
C7 C8 C9 120(2) . . ?
C7 C8 H8 120.0 . . ?
C9 C8 H8 120.0 . . ?
C10 C9 C8 119(2) . . ?
C10 C9 H9 120.7 . . ?
C8 C9 H9 120.6 . . ?
C9 C10 C11 124(2) . . ?
C9 C10 Br1 114.7(18) . . ?
C11 C10 Br1 121.2(19) . . ?
C10 C11 C12 124(3) . . ?
C10 C11 C16 118(2) . . ?
C12 C11 C16 118(3) . . ?
C13 C12 C11 120(3) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C12 C13 C14 122(2) . . ?
C12 C13 H13 119.1 . . ?
C14 C13 H13 119.1 . . ?
C15 C14 C13 120(3) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C14 C15 C16 120(3) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C7 C16 C15 123(3) . . ?
C7 C16 C11 118(3) . . ?
C15 C16 C11 118(2) . . ?
C3 N1 C4 119(2) . . ?
C3 N1 Hg1 121.4(14) . . ?
C4 N1 Hg1 119.0(16) . . ?
C6 N2 C7 124(2) . . ?
N1 Hg1 I1 113.1(4) . . ?
N1 Hg1 I2 98.5(4) . . ?
I1 Hg1 I2 129.45(7) . . ?
N1 Hg1 I2 98.0(4) . 2_553 ?
I1 Hg1 I2 109.52(6) . 2_553 ?
I2 Hg1 I2 103.49(7) . 2_553 ?
Hg1 I2 Hg1 102.95(6) . 2_543 ?

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
C5 C1 C2 C3 3(4) . . . . ?
C1 C2 C3 N1 -4(4) . . . . ?
N1 C4 C5 C6 174(3) . . . . ?
N1 C4 C5 C1 1(4) . . . . ?
C2 C1 C5 C4 -2(4) . . . . ?
C2 C1 C5 C6 -175(3) . . . . ?
C4 C5 C6 N2 -174(3) . . . . ?
C1 C5 C6 N2 -1(4) . . . . ?
C16 C7 C8 C9 -4(4) . . . . ?
N2 C7 C8 C9 180(3) . . . . ?
C7 C8 C9 C10 -1(5) . . . . ?
C8 C9 C10 C11 3(5) . . . . ?
C8 C9 C10 Br1 -178(2) . . . . ?
C9 C10 C11 C12 175(3) . . . . ?
Br1 C10 C11 C12 -3(4) . . . . ?
C9 C10 C11 C16 0(4) . . . . ?
Br1 C10 C11 C16 -178.4(19) . . . . ?
C10 C11 C12 C13 -174(3) . . . . ?
C16 C11 C12 C13 2(4) . . . . ?
C11 C12 C13 C14 -5(4) . . . . ?
C12 C13 C14 C15 7(4) . . . . ?
C13 C14 C15 C16 -6(4) . . . . ?
C8 C7 C16 C15 -173(3) . . . . ?
N2 C7 C16 C15 3(4) . . . . ?
C8 C7 C16 C11 7(4) . . . . ?
N2 C7 C16 C11 -176(2) . . . . ?
C14 C15 C16 C7 -177(3) . . . . ?
C14 C15 C16 C11 2(4) . . . . ?
C10 C11 C16 C7 -5(4) . . . . ?
C12 C11 C16 C7 179(2) . . . . ?
C10 C11 C16 C15 175(2) . . . . ?
C12 C11 C16 C15 0(4) . . . . ?
C2 C3 N1 C4 3(4) . . . . ?
C2 C3 N1 Hg1 175(2) . . . . ?
C5 C4 N1 C3 -1(4) . . . . ?
C5 C4 N1 Hg1 -174(2) . . . . ?
C5 C6 N2 C7 -179(3) . . . . ?
C8 C7 N2 C6 -45(4) . . . . ?
C16 C7 N2 C6 139(3) . . . . ?
C3 N1 Hg1 I1 -69.2(18) . . . . ?
C4 N1 Hg1 I1 103.4(17) . . . . ?
C3 N1 Hg1 I2 151.1(17) . . . . ?
C4 N1 Hg1 I2 -36.3(18) . . . . ?
C3 N1 Hg1 I2 46.1(18) . . . 2_553 ?
C4 N1 Hg1 I2 -141.3(17) . . . 2_553 ?
N1 Hg1 I2 Hg1 94.8(4) . . . 2_543 ?
I1 Hg1 I2 Hg1 -34.89(10) . . . 2_543 ?
I2 Hg1 I2 Hg1 -164.87(7) 2_553 . . 2_543 ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         1.135
_refine_diff_density_min         -1.071
_refine_diff_density_rms         0.204
####################################################################### 
# 
# 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_d
_database_code_depnum_ccdc_archive 'CCDC 1471190'
_audit_update_record             
;
2016-03-29 deposited with the CCDC.
2016-06-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H22 Cl4 Hg1 N4 O2'
_chemical_formula_weight         836.93

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   26.559(5)
_cell_length_b                   4.7805(9)
_cell_length_c                   29.195(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 125.788(14)
_cell_angle_gamma                90.00
_cell_volume                     3006.9(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    12721
_cell_measurement_theta_min      1.65
_cell_measurement_theta_max      27.00

_exptl_crystal_description       Needle
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.849
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1624
_exptl_absorpt_coefficient_mu    5.512
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.2536
_exptl_absorpt_correction_T_max  0.5469
_exptl_absorpt_process_details   'shape of crystal determined optically'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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  'STOE IPDS II'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean '0.15 mm'
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12721
_diffrn_reflns_av_R_equivalents  0.0918
_diffrn_reflns_av_sigmaI/netI    0.0920
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_theta_min         1.65
_diffrn_reflns_theta_max         27.00
_reflns_number_total             3273
_reflns_number_gt                3030
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_cell_refinement       'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_data_reduction        'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0987P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3273
_refine_ls_number_parameters     195
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0652
_refine_ls_R_factor_gt           0.0512
_refine_ls_wR_factor_ref         0.1211
_refine_ls_wR_factor_gt          0.1012
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.010
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.005

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
C5 C 0.5420(7) 1.036(3) 0.8916(6) 0.041(4) Uani 1 1 d . . .
C8 C 0.4250(9) 1.182(3) 0.9546(7) 0.061(5) Uani 1 1 d . . .
H8 H 0.4617 1.2841 0.9754 0.074 Uiso 1 1 calc R . .
C7 C 0.4179(7) 1.000(3) 0.9165(6) 0.038(4) Uani 1 1 d . . .
C11 C 0.3134(8) 0.884(3) 0.8916(7) 0.054(4) Uani 1 1 d . . .
N2 N 0.4619(6) 0.957(2) 0.9056(5) 0.048(3) Uani 1 1 d . . .
H2A H 0.4641 0.7887 0.8964 0.058 Uiso 1 1 calc R . .
Cl2 Cl 0.2715(2) 1.1355(11) 0.9480(2) 0.0830(16) Uani 1 1 d . . .
O1 O 0.5051(5) 1.3910(19) 0.9226(5) 0.063(3) Uani 1 1 d . . .
C14 C 0.2930(9) 0.520(3) 0.8074(7) 0.067(5) Uani 1 1 d . . .
H14 H 0.2853 0.4032 0.7785 0.080 Uiso 1 1 calc R . .
C15 C 0.3476(8) 0.660(3) 0.8399(7) 0.054(4) Uani 1 1 d . . .
H15 H 0.3781 0.6277 0.8343 0.065 Uiso 1 1 calc R . .
C16 C 0.3596(7) 0.850(3) 0.8811(7) 0.048(4) Uani 1 1 d . . .
C12 C 0.2572(9) 0.740(4) 0.8578(9) 0.070(5) Uani 1 1 d . . .
H12 H 0.2258 0.7711 0.8623 0.084 Uiso 1 1 calc R . .
C6 C 0.5014(7) 1.142(3) 0.9073(6) 0.045(4) Uani 1 1 d . . .
C4 C 0.5184(7) 0.846(3) 0.8482(7) 0.044(4) Uani 1 1 d . . .
H4 H 0.4786 0.7768 0.8318 0.053 Uiso 1 1 calc R . .
C3 C 0.6060(7) 0.853(3) 0.8532(6) 0.051(4) Uani 1 1 d . . .
H3 H 0.6288 0.7886 0.8405 0.061 Uiso 1 1 calc R . .
C13 C 0.2481(9) 0.555(4) 0.8183(8) 0.075(5) Uani 1 1 d . . .
H13 H 0.2118 0.4499 0.7982 0.090 Uiso 1 1 calc R . .
Hg1 Hg 0.5000 0.4203(2) 0.7500 0.0580(4) Uani 1 2 d S . .
N1 N 0.5502(6) 0.757(3) 0.8288(5) 0.049(3) Uani 1 1 d . . .
C2 C 0.6348(8) 1.051(4) 0.8982(7) 0.066(5) Uani 1 1 d . . .
H2 H 0.6754 1.1117 0.9152 0.079 Uiso 1 1 calc R . .
C9 C 0.3806(8) 1.228(4) 0.9652(6) 0.057(4) Uani 1 1 d . . .
H9 H 0.3874 1.3532 0.9926 0.069 Uiso 1 1 calc R . .
C10 C 0.3268(8) 1.078(4) 0.9331(7) 0.058(4) Uani 1 1 d . . .
C1 C 0.5993(7) 1.146(3) 0.9145(7) 0.049(4) Uani 1 1 d . . .
H1 H 0.6143 1.2866 0.9416 0.059 Uiso 1 1 calc R . .
Cl1 Cl 0.4137(2) 0.3241(10) 0.7508(2) 0.0720(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
C5 C1 1.36(2) . ?
C5 C4 1.374(19) . ?
C5 C6 1.49(2) . ?
C8 C7 1.33(2) . ?
C8 C9 1.40(2) . ?
C8 H8 0.9300 . ?
C7 N2 1.396(17) . ?
C7 C16 1.45(2) . ?
C11 C12 1.40(2) . ?
C11 C10 1.40(2) . ?
C11 C16 1.44(2) . ?
N2 C6 1.351(17) . ?
N2 H2A 0.8600 . ?
Cl2 C10 1.781(16) . ?
O1 C6 1.255(15) . ?
C14 C15 1.36(2) . ?
C14 C13 1.41(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.39(2) . ?
C15 H15 0.9300 . ?
C12 C13 1.36(3) . ?
C12 H12 0.9300 . ?
C4 N1 1.331(17) . ?
C4 H4 0.9300 . ?
C3 N1 1.296(18) . ?
C3 C2 1.42(2) . ?
C3 H3 0.9300 . ?
C13 H13 0.9300 . ?
Hg1 Cl1 2.352(5) . ?
Hg1 Cl1 2.352(5) 2_656 ?
Hg1 N1 2.466(13) 2_656 ?
Hg1 N1 2.466(13) . ?
C2 C1 1.36(2) . ?
C2 H2 0.9300 . ?
C9 C10 1.37(2) . ?
C9 H9 0.9300 . ?
C1 H1 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 C5 C4 119.0(13) . . ?
C1 C5 C6 121.4(13) . . ?
C4 C5 C6 119.2(13) . . ?
C7 C8 C9 123.9(17) . . ?
C7 C8 H8 118.1 . . ?
C9 C8 H8 118.1 . . ?
C8 C7 N2 123.8(14) . . ?
C8 C7 C16 119.3(14) . . ?
N2 C7 C16 116.7(12) . . ?
C12 C11 C10 124.6(16) . . ?
C12 C11 C16 118.9(16) . . ?
C10 C11 C16 116.4(15) . . ?
C6 N2 C7 129.1(12) . . ?
C6 N2 H2A 115.5 . . ?
C7 N2 H2A 115.5 . . ?
C15 C14 C13 118.8(16) . . ?
C15 C14 H14 120.6 . . ?
C13 C14 H14 120.6 . . ?
C14 C15 C16 122.6(17) . . ?
C14 C15 H15 118.7 . . ?
C16 C15 H15 118.7 . . ?
C15 C16 C11 117.9(16) . . ?
C15 C16 C7 123.3(14) . . ?
C11 C16 C7 118.6(14) . . ?
C13 C12 C11 120.7(17) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
O1 C6 N2 122.3(14) . . ?
O1 C6 C5 120.8(13) . . ?
N2 C6 C5 117.0(12) . . ?
N1 C4 C5 122.8(14) . . ?
N1 C4 H4 118.6 . . ?
C5 C4 H4 118.6 . . ?
N1 C3 C2 124.6(15) . . ?
N1 C3 H3 117.7 . . ?
C2 C3 H3 117.7 . . ?
C12 C13 C14 120.8(18) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 H13 119.6 . . ?
Cl1 Hg1 Cl1 157.4(2) . 2_656 ?
Cl1 Hg1 N1 98.0(3) . 2_656 ?
Cl1 Hg1 N1 96.7(3) 2_656 2_656 ?
Cl1 Hg1 N1 96.7(3) . . ?
Cl1 Hg1 N1 98.0(3) 2_656 . ?
N1 Hg1 N1 98.4(6) 2_656 . ?
C3 N1 C4 117.3(14) . . ?
C3 N1 Hg1 124.4(10) . . ?
C4 N1 Hg1 118.3(10) . . ?
C1 C2 C3 115.8(15) . . ?
C1 C2 H2 122.1 . . ?
C3 C2 H2 122.1 . . ?
C10 C9 C8 116.4(15) . . ?
C10 C9 H9 121.8 . . ?
C8 C9 H9 121.8 . . ?
C9 C10 C11 125.2(15) . . ?
C9 C10 Cl2 115.8(13) . . ?
C11 C10 Cl2 119.0(14) . . ?
C2 C1 C5 120.2(14) . . ?
C2 C1 H1 119.9 . . ?
C5 C1 H1 119.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 C8 C7 N2 179.2(14) . . . . ?
C9 C8 C7 C16 4(2) . . . . ?
C8 C7 N2 C6 -33(2) . . . . ?
C16 C7 N2 C6 142.3(15) . . . . ?
C13 C14 C15 C16 -4(2) . . . . ?
C14 C15 C16 C11 4(2) . . . . ?
C14 C15 C16 C7 179.5(14) . . . . ?
C12 C11 C16 C15 -4(2) . . . . ?
C10 C11 C16 C15 -179.6(14) . . . . ?
C12 C11 C16 C7 -179.8(13) . . . . ?
C10 C11 C16 C7 4.6(19) . . . . ?
C8 C7 C16 C15 179.1(14) . . . . ?
N2 C7 C16 C15 3(2) . . . . ?
C8 C7 C16 C11 -5.4(19) . . . . ?
N2 C7 C16 C11 178.9(12) . . . . ?
C10 C11 C12 C13 179.9(17) . . . . ?
C16 C11 C12 C13 5(2) . . . . ?
C7 N2 C6 O1 3(3) . . . . ?
C7 N2 C6 C5 -178.1(13) . . . . ?
C1 C5 C6 O1 29(2) . . . . ?
C4 C5 C6 O1 -143.4(15) . . . . ?
C1 C5 C6 N2 -149.7(15) . . . . ?
C4 C5 C6 N2 37.9(19) . . . . ?
C1 C5 C4 N1 2(2) . . . . ?
C6 C5 C4 N1 174.9(13) . . . . ?
C11 C12 C13 C14 -5(3) . . . . ?
C15 C14 C13 C12 5(3) . . . . ?
C2 C3 N1 C4 -2(2) . . . . ?
C2 C3 N1 Hg1 179.0(12) . . . . ?
C5 C4 N1 C3 1(2) . . . . ?
C5 C4 N1 Hg1 -179.3(10) . . . . ?
Cl1 Hg1 N1 C3 169.5(11) . . . . ?
Cl1 Hg1 N1 C3 6.7(12) 2_656 . . . ?
N1 Hg1 N1 C3 -91.4(12) 2_656 . . . ?
Cl1 Hg1 N1 C4 -9.9(10) . . . . ?
Cl1 Hg1 N1 C4 -172.7(10) 2_656 . . . ?
N1 Hg1 N1 C4 89.2(10) 2_656 . . . ?
N1 C3 C2 C1 -2(2) . . . . ?
C7 C8 C9 C10 -1(2) . . . . ?
C8 C9 C10 C11 1(3) . . . . ?
C8 C9 C10 Cl2 179.0(12) . . . . ?
C12 C11 C10 C9 -177.7(16) . . . . ?
C16 C11 C10 C9 -2(2) . . . . ?
C12 C11 C10 Cl2 4(2) . . . . ?
C16 C11 C10 Cl2 179.3(11) . . . . ?
C3 C2 C1 C5 5(2) . . . . ?
C4 C5 C1 C2 -6(2) . . . . ?
C6 C5 C1 C2 -178.0(14) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         1.120
_refine_diff_density_min         -1.102
_refine_diff_density_rms         0.266
####################################################################### 
# 
# 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_d
_database_code_depnum_ccdc_archive 'CCDC 1471191'
_audit_update_record             
;
2016-03-29 deposited with the CCDC.
2016-06-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H22 Br4 Hg1 N4 O2'
_chemical_formula_weight         1014.73

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   26.927(2)
_cell_length_b                   4.7733(4)
_cell_length_c                   29.451(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 125.358(6)
_cell_angle_gamma                90.00
_cell_volume                     3087.2(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    13232
_cell_measurement_theta_min      2.77
_cell_measurement_theta_max      27.00

_exptl_crystal_description       Needle
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.183
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1912
_exptl_absorpt_coefficient_mu    10.200
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.6777
_exptl_absorpt_correction_T_max  0.8235
_exptl_absorpt_process_details   'shape of crystal determined optically'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      298(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  'STOE IPDS II'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean '0.15 mm'
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13232
_diffrn_reflns_av_R_equivalents  0.0918
_diffrn_reflns_av_sigmaI/netI    0.0825
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_theta_min         2.77
_diffrn_reflns_theta_max         27.00
_reflns_number_total             3359
_reflns_number_gt                1884
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_cell_refinement       'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_data_reduction        'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0559P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3359
_refine_ls_number_parameters     195
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0910
_refine_ls_R_factor_gt           0.0895
_refine_ls_wR_factor_ref         0.1709
_refine_ls_wR_factor_gt          0.1487
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.012
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.001

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 0.4028(7) 1.156(3) 0.0864(7) 0.044(4) Uani 1 1 d . . .
H1 H 0.3879 1.2942 0.0593 0.052 Uiso 1 1 calc R . .
C2 C 0.3678(7) 1.065(4) 0.1037(7) 0.052(4) Uani 1 1 d . . .
H2 H 0.3287 1.1341 0.0878 0.063 Uiso 1 1 calc R . .
C3 C 0.3926(7) 0.869(3) 0.1450(7) 0.047(4) Uani 1 1 d . . .
H3 H 0.3691 0.8057 0.1566 0.056 Uiso 1 1 calc R . .
C4 C 0.4812(8) 0.851(3) 0.1504(7) 0.043(4) Uani 1 1 d . . .
H4 H 0.5198 0.7770 0.1664 0.052 Uiso 1 1 calc R . .
C5 C 0.4601(6) 1.044(3) 0.1087(6) 0.036(3) Uani 1 1 d . . .
C6 C 0.4983(7) 1.150(3) 0.0909(7) 0.041(4) Uani 1 1 d . . .
C7 C 0.5820(7) 1.009(3) 0.0837(6) 0.035(4) Uani 1 1 d . . .
C8 C 0.5722(7) 1.184(3) 0.0441(7) 0.047(4) Uani 1 1 d . . .
H8 H 0.5356 1.2811 0.0228 0.057 Uiso 1 1 calc R . .
C9 C 0.6181(7) 1.224(3) 0.0344(7) 0.050(4) Uani 1 1 d . . .
H9 H 0.6115 1.3470 0.0069 0.060 Uiso 1 1 calc R . .
C10 C 0.6703(7) 1.083(3) 0.0653(7) 0.046(4) Uani 1 1 d . . .
C11 C 0.6835(7) 0.889(3) 0.1077(7) 0.048(4) Uani 1 1 d . . .
C12 C 0.7391(7) 0.732(4) 0.1417(8) 0.056(5) Uani 1 1 d . . .
H12 H 0.7694 0.7520 0.1359 0.067 Uiso 1 1 calc R . .
C13 C 0.7480(8) 0.559(4) 0.1811(8) 0.062(5) Uani 1 1 d . . .
H13 H 0.7844 0.4603 0.2028 0.075 Uiso 1 1 calc R . .
C14 C 0.7036(8) 0.526(3) 0.1900(7) 0.055(4) Uani 1 1 d . . .
H14 H 0.7106 0.3982 0.2169 0.066 Uiso 1 1 calc R . .
C15 C 0.6498(7) 0.670(3) 0.1615(7) 0.044(4) Uani 1 1 d . . .
H15 H 0.6223 0.6501 0.1707 0.052 Uiso 1 1 calc R . .
C16 C 0.6366(7) 0.852(3) 0.1168(7) 0.043(4) Uani 1 1 d . . .
N1 N 0.4489(6) 0.763(2) 0.1699(5) 0.044(3) Uani 1 1 d . . .
N2 N 0.5371(5) 0.960(3) 0.0939(5) 0.043(3) Uani 1 1 d . . .
H2A H 0.5345 0.7921 0.1030 0.052 Uiso 1 1 calc R . .
O1 O 0.4948(5) 1.3944(19) 0.0768(5) 0.052(3) Uani 1 1 d . . .
Hg1 Hg 0.5000 0.4455(2) 0.2500 0.0433(3) Uani 1 2 d S . .
Br1 Br 0.59027(8) 0.3335(4) 0.25030(8) 0.0583(5) Uani 1 1 d . . .
Br2 Br 0.72971(9) 1.1404(4) 0.05003(9) 0.0720(6) 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
C1 C2 1.38(2) . ?
C1 C5 1.39(2) . ?
C1 H1 0.9300 . ?
C2 C3 1.36(2) . ?
C2 H2 0.9300 . ?
C3 N1 1.343(18) . ?
C3 H3 0.9300 . ?
C4 N1 1.358(19) . ?
C4 C5 1.37(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.49(2) . ?
C6 O1 1.223(16) . ?
C6 N2 1.348(19) . ?
C7 C8 1.33(2) . ?
C7 C16 1.42(2) . ?
C7 N2 1.424(18) . ?
C8 C9 1.43(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.33(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.42(2) . ?
C10 Br2 1.915(15) . ?
C11 C12 1.44(2) . ?
C11 C16 1.45(2) . ?
C12 C13 1.33(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.37(2) . ?
C13 H13 0.9300 . ?
C14 C15 1.37(2) . ?
C14 H14 0.9300 . ?
C15 C16 1.44(2) . ?
C15 H15 0.9300 . ?
N1 Hg1 2.447(12) . ?
N2 H2A 0.8600 . ?
Hg1 N1 2.447(13) 2_655 ?
Hg1 Br1 2.4838(18) 2_655 ?
Hg1 Br1 2.4838(18) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C5 121.0(14) . . ?
C2 C1 H1 119.5 . . ?
C5 C1 H1 119.5 . . ?
C3 C2 C1 117.3(14) . . ?
C3 C2 H2 121.4 . . ?
C1 C2 H2 121.4 . . ?
N1 C3 C2 124.4(15) . . ?
N1 C3 H3 117.8 . . ?
C2 C3 H3 117.8 . . ?
N1 C4 C5 123.8(14) . . ?
N1 C4 H4 118.1 . . ?
C5 C4 H4 118.1 . . ?
C4 C5 C1 117.1(14) . . ?
C4 C5 C6 122.3(13) . . ?
C1 C5 C6 120.5(14) . . ?
O1 C6 N2 124.7(15) . . ?
O1 C6 C5 120.8(14) . . ?
N2 C6 C5 114.5(13) . . ?
C8 C7 C16 122.4(14) . . ?
C8 C7 N2 121.7(13) . . ?
C16 C7 N2 115.9(12) . . ?
C7 C8 C9 120.1(14) . . ?
C7 C8 H8 120.0 . . ?
C9 C8 H8 120.0 . . ?
C10 C9 C8 119.2(15) . . ?
C10 C9 H9 120.4 . . ?
C8 C9 H9 120.4 . . ?
C9 C10 C11 123.8(15) . . ?
C9 C10 Br2 117.5(13) . . ?
C11 C10 Br2 118.7(12) . . ?
C10 C11 C12 125.4(16) . . ?
C10 C11 C16 116.2(14) . . ?
C12 C11 C16 118.4(16) . . ?
C13 C12 C11 121.3(17) . . ?
C13 C12 H12 119.3 . . ?
C11 C12 H12 119.3 . . ?
C12 C13 C14 120.1(16) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C15 C14 C13 123.8(16) . . ?
C15 C14 H14 118.1 . . ?
C13 C14 H14 118.1 . . ?
C14 C15 C16 118.6(15) . . ?
C14 C15 H15 120.7 . . ?
C16 C15 H15 120.7 . . ?
C7 C16 C15 123.9(14) . . ?
C7 C16 C11 118.4(14) . . ?
C15 C16 C11 117.6(14) . . ?
C3 N1 C4 116.4(14) . . ?
C3 N1 Hg1 126.2(11) . . ?
C4 N1 Hg1 117.4(10) . . ?
C6 N2 C7 126.7(12) . . ?
C6 N2 H2A 116.7 . . ?
C7 N2 H2A 116.7 . . ?
N1 Hg1 N1 103.6(6) . 2_655 ?
N1 Hg1 Br1 97.2(3) . 2_655 ?
N1 Hg1 Br1 98.1(3) 2_655 2_655 ?
N1 Hg1 Br1 98.1(3) . . ?
N1 Hg1 Br1 97.2(3) 2_655 . ?
Br1 Hg1 Br1 155.14(9) 2_655 . ?

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
C5 C1 C2 C3 2(2) . . . . ?
C1 C2 C3 N1 1(3) . . . . ?
N1 C4 C5 C1 1(2) . . . . ?
N1 C4 C5 C6 175.9(13) . . . . ?
C2 C1 C5 C4 -3(2) . . . . ?
C2 C1 C5 C6 -178.1(15) . . . . ?
C4 C5 C6 O1 -143.4(16) . . . . ?
C1 C5 C6 O1 31(2) . . . . ?
C4 C5 C6 N2 34(2) . . . . ?
C1 C5 C6 N2 -151.3(15) . . . . ?
C16 C7 C8 C9 -1(2) . . . . ?
N2 C7 C8 C9 -179.0(14) . . . . ?
C7 C8 C9 C10 0(2) . . . . ?
C8 C9 C10 C11 1(3) . . . . ?
C8 C9 C10 Br2 179.2(12) . . . . ?
C9 C10 C11 C12 179.7(16) . . . . ?
Br2 C10 C11 C12 1(2) . . . . ?
C9 C10 C11 C16 -1(2) . . . . ?
Br2 C10 C11 C16 -179.2(10) . . . . ?
C10 C11 C12 C13 178.7(17) . . . . ?
C16 C11 C12 C13 -1(2) . . . . ?
C11 C12 C13 C14 0(3) . . . . ?
C12 C13 C14 C15 -2(3) . . . . ?
C13 C14 C15 C16 5(3) . . . . ?
C8 C7 C16 C15 177.2(15) . . . . ?
N2 C7 C16 C15 -5(2) . . . . ?
C8 C7 C16 C11 1(2) . . . . ?
N2 C7 C16 C11 179.0(13) . . . . ?
C14 C15 C16 C7 179.0(14) . . . . ?
C14 C15 C16 C11 -5(2) . . . . ?
C10 C11 C16 C7 0(2) . . . . ?
C12 C11 C16 C7 179.5(13) . . . . ?
C10 C11 C16 C15 -176.5(13) . . . . ?
C12 C11 C16 C15 3(2) . . . . ?
C2 C3 N1 C4 -3(2) . . . . ?
C2 C3 N1 Hg1 173.8(13) . . . . ?
C5 C4 N1 C3 2(2) . . . . ?
C5 C4 N1 Hg1 -175.2(11) . . . . ?
O1 C6 N2 C7 3(2) . . . . ?
C5 C6 N2 C7 -174.9(13) . . . . ?
C8 C7 N2 C6 -36(2) . . . . ?
C16 C7 N2 C6 145.5(14) . . . . ?
C3 N1 Hg1 N1 -88.7(12) . . . 2_655 ?
C4 N1 Hg1 N1 87.7(10) . . . 2_655 ?
C3 N1 Hg1 Br1 11.5(12) . . . 2_655 ?
C4 N1 Hg1 Br1 -172.1(10) . . . 2_655 ?
C3 N1 Hg1 Br1 171.8(12) . . . . ?
C4 N1 Hg1 Br1 -11.8(10) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         1.052
_refine_diff_density_min         -1.115
_refine_diff_density_rms         0.311
####################################################################### 
# 
# 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_d
_database_code_depnum_ccdc_archive 'CCDC 1471192'
_audit_update_record             
;
2016-03-29 deposited with the CCDC.
2016-06-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H22 Br2 Hg1 I2 N4 O2'
_chemical_formula_weight         1108.73

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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   27.265(3)
_cell_length_b                   4.7826(9)
_cell_length_c                   26.369(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 112.507(11)
_cell_angle_gamma                90.00
_cell_volume                     3176.5(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    13156
_cell_measurement_theta_min      1.62
_cell_measurement_theta_max      27.00

_exptl_crystal_description       Needle
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.318
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2056
_exptl_absorpt_coefficient_mu    9.341
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.0950
_exptl_absorpt_correction_T_max  0.4515
_exptl_absorpt_process_details   'shape of crystal determined optically'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      298(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  'STOE IPDS II'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean '0.15 mm'
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13156
_diffrn_reflns_av_R_equivalents  0.0812
_diffrn_reflns_av_sigmaI/netI    0.0652
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         1.62
_diffrn_reflns_theta_max         26.99
_reflns_number_total             3460
_reflns_number_gt                2250
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_cell_refinement       'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_data_reduction        'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0371P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3460
_refine_ls_number_parameters     195
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0812
_refine_ls_R_factor_gt           0.0777
_refine_ls_wR_factor_ref         0.1911
_refine_ls_wR_factor_gt          0.1260
_refine_ls_goodness_of_fit_ref   0.992
_refine_ls_restrained_S_all      0.992
_refine_ls_shift/su_max          0.004
_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 0.5697(10) 1.405(4) 0.4174(11) 0.063(7) Uani 1 1 d . . .
H1 H 0.5817 1.5392 0.4449 0.075 Uiso 1 1 calc R . .
C2 C 0.5163(9) 1.307(6) 0.3981(12) 0.073(8) Uani 1 1 d . . .
H2 H 0.4930 1.3734 0.4134 0.087 Uiso 1 1 calc R . .
C3 C 0.5000(10) 1.112(5) 0.3562(12) 0.065(7) Uani 1 1 d . . .
H3 H 0.4655 1.0431 0.3446 0.078 Uiso 1 1 calc R . .
C4 C 0.5810(9) 1.107(4) 0.3517(10) 0.053(6) Uani 1 1 d . . .
H4 H 0.6036 1.0360 0.3359 0.064 Uiso 1 1 calc R . .
C5 C 0.6022(8) 1.299(4) 0.3950(10) 0.055(6) Uani 1 1 d . . .
C6 C 0.6591(9) 1.415(5) 0.4120(11) 0.057(7) Uani 1 1 d . . .
C7 C 0.7475(9) 1.254(5) 0.4164(12) 0.069(8) Uani 1 1 d . . .
C8 C 0.7784(9) 1.435(5) 0.4553(10) 0.058(6) Uani 1 1 d . . .
H8 H 0.7631 1.5372 0.4755 0.070 Uiso 1 1 calc R . .
C9 C 0.8321(9) 1.473(5) 0.4660(11) 0.064(7) Uani 1 1 d . . .
H9 H 0.8528 1.5908 0.4942 0.077 Uiso 1 1 calc R . .
C10 C 0.8537(9) 1.337(5) 0.4350(12) 0.070(8) Uani 1 1 d . . .
C11 C 0.8255(9) 1.137(5) 0.3943(12) 0.066(8) Uani 1 1 d . . .
C12 C 0.8456(11) 0.977(5) 0.3613(12) 0.074(8) Uani 1 1 d . . .
H12 H 0.8815 0.9895 0.3674 0.089 Uiso 1 1 calc R . .
C13 C 0.8133(12) 0.802(6) 0.3201(14) 0.102(10) Uani 1 1 d . . .
H13 H 0.8270 0.7026 0.2982 0.123 Uiso 1 1 calc R . .
C14 C 0.7599(11) 0.777(5) 0.3122(10) 0.066(7) Uani 1 1 d . . .
H14 H 0.7385 0.6546 0.2854 0.080 Uiso 1 1 calc R . .
C15 C 0.7383(10) 0.925(5) 0.3425(13) 0.077(9) Uani 1 1 d . . .
H15 H 0.7023 0.9061 0.3353 0.093 Uiso 1 1 calc R . .
C16 C 0.7690(10) 1.106(4) 0.3842(11) 0.057(7) Uani 1 1 d . . .
N1 N 0.5312(8) 1.020(3) 0.3318(9) 0.066(6) Uani 1 1 d . . .
N2 N 0.6935(7) 1.214(4) 0.4088(8) 0.062(6) Uani 1 1 d . . .
H2A H 0.6812 1.0464 0.4015 0.074 Uiso 1 1 calc R . .
O1 O 0.6704(6) 1.648(3) 0.4257(8) 0.076(6) Uani 1 1 d . . .
Hg1 Hg 0.5000 0.7110(3) 0.2500 0.0607(5) Uani 1 2 d S . .
Br1 Br 0.92748(11) 1.3872(6) 0.44902(15) 0.0936(11) Uani 1 1 d . . .
I1 I 0.40598(7) 0.5871(3) 0.25180(8) 0.0729(6) 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
C1 C5 1.34(3) . ?
C1 C2 1.42(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.38(3) . ?
C2 H2 0.9300 . ?
C3 N1 1.32(3) . ?
C3 H3 0.9300 . ?
C4 N1 1.32(3) . ?
C4 C5 1.41(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.54(3) . ?
C6 O1 1.18(2) . ?
C6 N2 1.37(3) . ?
C7 C8 1.36(3) . ?
C7 C16 1.40(3) . ?
C7 N2 1.42(3) . ?
C8 C9 1.39(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.34(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.42(3) . ?
C10 Br1 1.92(2) . ?
C11 C12 1.42(3) . ?
C11 C16 1.47(3) . ?
C12 C13 1.39(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.39(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.36(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.40(3) . ?
C15 H15 0.9300 . ?
N1 Hg1 2.48(2) . ?
N2 H2A 0.8600 . ?
Hg1 N1 2.48(2) 2_655 ?
Hg1 I1 2.6491(17) . ?
Hg1 I1 2.6492(17) 2_655 ?

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
C5 C1 C2 119(2) . . ?
C5 C1 H1 120.7 . . ?
C2 C1 H1 120.7 . . ?
C3 C2 C1 119(2) . . ?
C3 C2 H2 120.7 . . ?
C1 C2 H2 120.7 . . ?
N1 C3 C2 123(2) . . ?
N1 C3 H3 118.6 . . ?
C2 C3 H3 118.6 . . ?
N1 C4 C5 125(2) . . ?
N1 C4 H4 117.7 . . ?
C5 C4 H4 117.7 . . ?
C1 C5 C4 118(2) . . ?
C1 C5 C6 120(2) . . ?
C4 C5 C6 122(2) . . ?
O1 C6 N2 125(2) . . ?
O1 C6 C5 123(2) . . ?
N2 C6 C5 111.4(19) . . ?
C8 C7 C16 120(2) . . ?
C8 C7 N2 120(3) . . ?
C16 C7 N2 120(2) . . ?
C7 C8 C9 122(2) . . ?
C7 C8 H8 118.9 . . ?
C9 C8 H8 118.9 . . ?
C10 C9 C8 119(2) . . ?
C10 C9 H9 120.5 . . ?
C8 C9 H9 120.5 . . ?
C9 C10 C11 123(2) . . ?
C9 C10 Br1 120(2) . . ?
C11 C10 Br1 117(2) . . ?
C12 C11 C10 127(2) . . ?
C12 C11 C16 117(2) . . ?
C10 C11 C16 116(2) . . ?
C13 C12 C11 122(3) . . ?
C13 C12 H12 119.1 . . ?
C11 C12 H12 119.1 . . ?
C12 C13 C14 119(3) . . ?
C12 C13 H13 120.5 . . ?
C14 C13 H13 120.5 . . ?
C15 C14 C13 122(3) . . ?
C15 C14 H14 119.1 . . ?
C13 C14 H14 119.1 . . ?
C14 C15 C16 121(2) . . ?
C14 C15 H15 119.3 . . ?
C16 C15 H15 119.3 . . ?
C7 C16 C15 122(2) . . ?
C7 C16 C11 120(2) . . ?
C15 C16 C11 118(2) . . ?
C4 N1 C3 117(2) . . ?
C4 N1 Hg1 119.3(17) . . ?
C3 N1 Hg1 123.4(16) . . ?
C6 N2 C7 126.3(19) . . ?
C6 N2 H2A 116.8 . . ?
C7 N2 H2A 116.8 . . ?
N1 Hg1 N1 106.8(9) 2_655 . ?
N1 Hg1 I1 97.9(5) 2_655 . ?
N1 Hg1 I1 97.4(5) . . ?
N1 Hg1 I1 97.4(5) 2_655 2_655 ?
N1 Hg1 I1 97.9(5) . 2_655 ?
I1 Hg1 I1 154.14(9) . 2_655 ?

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
C5 C1 C2 C3 -2(4) . . . . ?
C1 C2 C3 N1 -3(4) . . . . ?
C2 C1 C5 C4 3(3) . . . . ?
C2 C1 C5 C6 176(2) . . . . ?
N1 C4 C5 C1 -1(3) . . . . ?
N1 C4 C5 C6 -173(2) . . . . ?
C1 C5 C6 O1 -31(4) . . . . ?
C4 C5 C6 O1 142(3) . . . . ?
C1 C5 C6 N2 150(2) . . . . ?
C4 C5 C6 N2 -38(3) . . . . ?
C16 C7 C8 C9 -2(4) . . . . ?
N2 C7 C8 C9 177(2) . . . . ?
C7 C8 C9 C10 3(4) . . . . ?
C8 C9 C10 C11 -5(4) . . . . ?
C8 C9 C10 Br1 179.9(17) . . . . ?
C9 C10 C11 C12 -177(3) . . . . ?
Br1 C10 C11 C12 -2(4) . . . . ?
C9 C10 C11 C16 6(4) . . . . ?
Br1 C10 C11 C16 -179.4(17) . . . . ?
C10 C11 C12 C13 -175(3) . . . . ?
C16 C11 C12 C13 1(4) . . . . ?
C11 C12 C13 C14 -2(4) . . . . ?
C12 C13 C14 C15 2(4) . . . . ?
C13 C14 C15 C16 -2(4) . . . . ?
C8 C7 C16 C15 -178(2) . . . . ?
N2 C7 C16 C15 3(3) . . . . ?
C8 C7 C16 C11 3(3) . . . . ?
N2 C7 C16 C11 -177(2) . . . . ?
C14 C15 C16 C7 -178(2) . . . . ?
C14 C15 C16 C11 1(4) . . . . ?
C12 C11 C16 C7 178(2) . . . . ?
C10 C11 C16 C7 -4(3) . . . . ?
C12 C11 C16 C15 -1(3) . . . . ?
C10 C11 C16 C15 176(2) . . . . ?
C5 C4 N1 C3 -3(3) . . . . ?
C5 C4 N1 Hg1 174.9(16) . . . . ?
C2 C3 N1 C4 5(3) . . . . ?
C2 C3 N1 Hg1 -173.1(17) . . . . ?
O1 C6 N2 C7 -6(4) . . . . ?
C5 C6 N2 C7 174(2) . . . . ?
C8 C7 N2 C6 38(4) . . . . ?
C16 C7 N2 C6 -143(2) . . . . ?
C4 N1 Hg1 N1 -88.2(15) . . . 2_655 ?
C3 N1 Hg1 N1 89.6(18) . . . 2_655 ?
C4 N1 Hg1 I1 171.2(15) . . . . ?
C3 N1 Hg1 I1 -11.0(18) . . . . ?
C4 N1 Hg1 I1 12.0(16) . . . 2_655 ?
C3 N1 Hg1 I1 -170.1(17) . . . 2_655 ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        26.99
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         1.250
_refine_diff_density_min         -1.271
_refine_diff_density_rms         0.168
####################################################################### 
# 
# 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_d
_database_code_depnum_ccdc_archive 'CCDC 1471193'
_audit_update_record             
;
2016-03-29 deposited with the CCDC.
2016-06-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H22 Br2 Cl2 Hg1 N4'
_chemical_formula_weight         893.83

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   37.566(4)
_cell_length_b                   5.2293(5)
_cell_length_c                   16.778(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 115.093(9)
_cell_angle_gamma                90.00
_cell_volume                     2984.9(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    13660
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      27.00

_exptl_crystal_description       Needle
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.989
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1704
_exptl_absorpt_coefficient_mu    8.043
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.2000
_exptl_absorpt_correction_T_max  0.6521
_exptl_absorpt_process_details   'shape of crystal determined optically'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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  'STOE IPDS II'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean '0.15 mm'
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13660
_diffrn_reflns_av_R_equivalents  0.0821
_diffrn_reflns_av_sigmaI/netI    0.1020
_diffrn_reflns_limit_h_min       -47
_diffrn_reflns_limit_h_max       47
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.43
_diffrn_reflns_theta_max         26.99
_reflns_number_total             6523
_reflns_number_gt                6253
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_cell_refinement       'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_data_reduction        'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.006(19)
_refine_ls_number_reflns         6523
_refine_ls_number_parameters     336
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0821
_refine_ls_R_factor_gt           0.0752
_refine_ls_wR_factor_ref         0.1423
_refine_ls_wR_factor_gt          0.1197
_refine_ls_goodness_of_fit_ref   0.960
_refine_ls_restrained_S_all      0.960
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.002

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 -0.0422(7) 0.603(5) 0.1587(15) 0.042(6) Uani 1 1 d . . .
H1A H -0.0488 0.7345 0.1872 0.050 Uiso 1 1 calc R . .
C2 C -0.0099(8) 0.488(5) 0.2008(13) 0.041(10) Uani 1 1 d . . .
H2A H 0.0068 0.5390 0.2575 0.082 Uiso 1 1 calc R . .
C3 C 0.0002(7) 0.284(4) 0.1606(17) 0.045(7) Uani 1 1 d . . .
H3 H 0.0233 0.1946 0.1924 0.054 Uiso 1 1 calc R . .
C4 C -0.0577(7) 0.331(4) 0.0354(15) 0.045(5) Uani 1 1 d . . .
H4 H -0.0756 0.2717 -0.0193 0.038 Uiso 1 1 calc R . .
C5 C -0.0678(6) 0.546(5) 0.0746(13) 0.037(6) Uani 1 1 d . . .
C6 C -0.1049(8) 0.678(4) 0.0241(18) 0.046(7) Uani 1 1 d . . .
H6 H -0.1229 0.6068 -0.0284 0.056 Uiso 1 1 calc R . .
C7 C -0.1456(7) 1.030(4) -0.0084(18) 0.033(7) Uani 1 1 d . . .
C8 C -0.1548(7) 1.052(5) -0.0960(14) 0.037(7) Uani 1 1 d . . .
H8 H -0.1411 0.9570 -0.1206 0.060 Uiso 1 1 calc R . .
C9 C -0.1835(7) 1.212(5) -0.1467(18) 0.049(7) Uani 1 1 d . . .
H9 H -0.1905 1.2191 -0.2069 0.059 Uiso 1 1 calc R . .
C10 C -0.2028(6) 1.367(5) -0.1099(17) 0.041(7) Uani 1 1 d . . .
C11 C -0.1934(7) 1.349(5) -0.0200(17) 0.031(7) Uani 1 1 d . . .
C12 C -0.2118(9) 1.518(5) 0.020(2) 0.038(8) Uani 1 1 d . . .
H12 H -0.2304 1.6369 -0.0144 0.074 Uiso 1 1 calc R . .
C13 C -0.2017(8) 1.503(5) 0.105(2) 0.035(9) Uani 1 1 d . . .
H13 H -0.2142 1.6131 0.1285 0.074 Uiso 1 1 calc R . .
C14 C -0.1736(8) 1.334(5) 0.163(2) 0.035(9) Uani 1 1 d . . .
H14 H -0.1679 1.3283 0.2225 0.076 Uiso 1 1 calc R . .
C15 C -0.1551(8) 1.178(4) 0.1266(17) 0.033(7) Uani 1 1 d . . .
H15 H -0.1366 1.0602 0.1617 0.057 Uiso 1 1 calc R . .
C16 C -0.1641(8) 1.195(4) 0.0352(19) 0.032(7) Uani 1 1 d . . .
C17 C 0.1077(7) 0.770(4) 0.6440(17) 0.051(7) Uani 1 1 d . . .
H17 H 0.1243 0.9092 0.6680 0.061 Uiso 1 1 calc R . .
C18 C 0.0934(7) 0.629(4) 0.6947(16) 0.044(6) Uani 1 1 d . . .
H18 H 0.1030 0.6567 0.7550 0.053 Uiso 1 1 calc R . .
C19 C 0.0664(7) 0.456(5) 0.6563(17) 0.048(7) Uani 1 1 d . . .
H19 H 0.0552 0.3756 0.6896 0.057 Uiso 1 1 calc R . .
C20 C 0.0680(7) 0.506(5) 0.5210(17) 0.051(7) Uani 1 1 d . . .
H20 H 0.0589 0.4620 0.4620 0.061 Uiso 1 1 calc R . .
C21 C 0.0963(8) 0.698(4) 0.5559(15) 0.042(6) Uani 1 1 d . . .
C22 C 0.1115(7) 0.844(4) 0.5038(16) 0.037(6) Uani 1 1 d . . .
H22 H 0.1073 0.7769 0.4492 0.045 Uiso 1 1 calc R . .
C23 C 0.1399(8) 1.195(5) 0.4686(16) 0.041(7) Uani 1 1 d . . .
C24 C 0.1193(7) 1.195(4) 0.3774(18) 0.047(7) Uani 1 1 d . . .
H24 H 0.0973 1.0905 0.3509 0.056 Uiso 1 1 calc R . .
C25 C 0.1310(7) 1.346(4) 0.3264(17) 0.050(7) Uani 1 1 d . . .
H25 H 0.1181 1.3313 0.2655 0.060 Uiso 1 1 calc R . .
C26 C 0.1608(7) 1.518(4) 0.3617(16) 0.039(6) Uani 1 1 d . . .
C27 C 0.1831(7) 1.531(5) 0.4543(17) 0.047(7) Uani 1 1 d . . .
C28 C 0.2130(7) 1.709(5) 0.500(2) 0.050(8) Uani 1 1 d . . .
H28 H 0.2197 1.8238 0.4666 0.060 Uiso 1 1 calc R . .
C29 C 0.2323(8) 1.727(5) 0.587(2) 0.042(8) Uani 1 1 d . . .
H29 H 0.2523 1.8470 0.6118 0.073 Uiso 1 1 calc R . .
C30 C 0.2222(8) 1.563(6) 0.6402(19) 0.049(9) Uani 1 1 d . . .
H30 H 0.2352 1.5742 0.7011 0.077 Uiso 1 1 calc R . .
C31 C 0.1929(7) 1.384(6) 0.6020(16) 0.049(6) Uani 1 1 d . . .
H31 H 0.1869 1.2746 0.6383 0.059 Uiso 1 1 calc R . .
C32 C 0.1716(7) 1.361(4) 0.5103(14) 0.034(6) Uani 1 1 d . . .
N1 N -0.0226(6) 0.214(3) 0.0770(11) 0.041(5) Uani 1 1 d . . .
N2 N -0.1128(5) 0.885(5) 0.0507(12) 0.040(6) Uani 1 1 d . . .
N3 N 0.0538(5) 0.386(4) 0.5716(13) 0.042(5) Uani 1 1 d . . .
N4 N 0.1294(6) 1.048(3) 0.5245(12) 0.047(5) Uani 1 1 d . . .
Hg1 Hg 0.0000 -0.0981(2) 0.0000 0.0340(5) Uani 1 2 d S . .
Hg2 Hg 0.0000 0.0843(3) 0.5000 0.0449(6) Uani 1 2 d S . .
Br1 Br -0.06249(8) -0.2036(5) -0.12824(19) 0.0594(8) Uani 1 1 d . . .
Br2 Br 0.01072(8) -0.0264(4) 0.36829(18) 0.0550(8) Uani 1 1 d . . .
Cl1 Cl -0.2397(2) 1.5697(16) -0.1802(5) 0.073(2) Uani 1 1 d . . .
Cl2 Cl 0.1741(3) 1.7184(15) 0.2969(5) 0.073(3) 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
C1 C2 1.26(3) . ?
C1 C5 1.36(3) . ?
C1 H1A 0.9300 . ?
C2 C3 1.40(3) . ?
C2 H2A 0.9300 . ?
C3 N1 1.35(3) . ?
C3 H3 0.9300 . ?
C4 N1 1.35(3) . ?
C4 C5 1.43(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.46(3) . ?
C6 N2 1.26(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.37(3) . ?
C7 N2 1.43(3) . ?
C7 C16 1.48(3) . ?
C8 C9 1.34(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.40(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.40(3) . ?
C10 Cl1 1.75(2) . ?
C11 C16 1.36(3) . ?
C11 C12 1.45(3) . ?
C12 C13 1.32(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.40(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.37(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.43(3) . ?
C15 H15 0.9300 . ?
C17 C18 1.39(3) . ?
C17 C21 1.41(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.31(3) . ?
C18 H18 0.9300 . ?
C19 N3 1.34(3) . ?
C19 H19 0.9300 . ?
C20 N3 1.34(3) . ?
C20 C21 1.40(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.45(3) . ?
C22 N4 1.23(3) . ?
C22 H22 0.9300 . ?
C23 N4 1.39(3) . ?
C23 C24 1.39(3) . ?
C23 C32 1.40(3) . ?
C24 C25 1.37(3) . ?
C24 H24 0.9300 . ?
C25 C26 1.36(3) . ?
C25 H25 0.9300 . ?
C26 C27 1.42(3) . ?
C26 Cl2 1.73(2) . ?
C27 C28 1.41(3) . ?
C27 C32 1.48(3) . ?
C28 C29 1.32(4) . ?
C28 H28 0.9300 . ?
C29 C30 1.41(3) . ?
C29 H29 0.9300 . ?
C30 C31 1.38(3) . ?
C30 H30 0.9300 . ?
C31 C32 1.41(3) . ?
C31 H31 0.9300 . ?
N1 Hg1 2.445(17) . ?
N3 Hg2 2.441(19) . ?
Hg1 N1 2.445(17) 2 ?
Hg1 Br1 2.482(3) 2 ?
Hg1 Br1 2.482(3) . ?
Hg2 N3 2.441(19) 2_556 ?
Hg2 Br2 2.477(2) 2_556 ?
Hg2 Br2 2.477(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
C2 C1 C5 124(2) . . ?
C2 C1 H1A 117.9 . . ?
C5 C1 H1A 117.8 . . ?
C1 C2 C3 119(2) . . ?
C1 C2 H2A 120.5 . . ?
C3 C2 H2A 120.5 . . ?
N1 C3 C2 122(2) . . ?
N1 C3 H3 119.1 . . ?
C2 C3 H3 119.0 . . ?
N1 C4 C5 121(2) . . ?
N1 C4 H4 119.6 . . ?
C5 C4 H4 119.7 . . ?
C1 C5 C4 116(2) . . ?
C1 C5 C6 126(2) . . ?
C4 C5 C6 118(2) . . ?
N2 C6 C5 121(2) . . ?
N2 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C8 C7 N2 123(2) . . ?
C8 C7 C16 122(2) . . ?
N2 C7 C16 114(2) . . ?
C9 C8 C7 120(3) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C8 C9 C10 121(3) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C9 C10 C11 120(2) . . ?
C9 C10 Cl1 118(2) . . ?
C11 C10 Cl1 122(2) . . ?
C16 C11 C10 122(2) . . ?
C16 C11 C12 117(3) . . ?
C10 C11 C12 120(2) . . ?
C13 C12 C11 119(3) . . ?
C13 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
C12 C13 C14 125(3) . . ?
C12 C13 H13 117.4 . . ?
C14 C13 H13 117.4 . . ?
C15 C14 C13 116(3) . . ?
C15 C14 H14 122.0 . . ?
C13 C14 H14 121.9 . . ?
C14 C15 C16 120(3) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C11 C16 C15 122(2) . . ?
C11 C16 C7 115(2) . . ?
C15 C16 C7 123(2) . . ?
C18 C17 C21 118(2) . . ?
C18 C17 H17 120.9 . . ?
C21 C17 H17 120.8 . . ?
C19 C18 C17 119(2) . . ?
C19 C18 H18 120.5 . . ?
C17 C18 H18 120.5 . . ?
C18 C19 N3 124(2) . . ?
C18 C19 H19 117.9 . . ?
N3 C19 H19 117.9 . . ?
N3 C20 C21 121(2) . . ?
N3 C20 H20 119.7 . . ?
C21 C20 H20 119.7 . . ?
C20 C21 C17 118(2) . . ?
C20 C21 C22 123(2) . . ?
C17 C21 C22 118(2) . . ?
N4 C22 C21 126(2) . . ?
N4 C22 H22 116.8 . . ?
C21 C22 H22 116.8 . . ?
N4 C23 C24 124(3) . . ?
N4 C23 C32 115(2) . . ?
C24 C23 C32 121(2) . . ?
C25 C24 C23 121(2) . . ?
C25 C24 H24 119.7 . . ?
C23 C24 H24 119.7 . . ?
C26 C25 C24 122(3) . . ?
C26 C25 H25 118.8 . . ?
C24 C25 H25 118.9 . . ?
C25 C26 C27 120(2) . . ?
C25 C26 Cl2 122(2) . . ?
C27 C26 Cl2 117.9(19) . . ?
C28 C27 C26 126(2) . . ?
C28 C27 C32 115(2) . . ?
C26 C27 C32 118(2) . . ?
C29 C28 C27 126(3) . . ?
C29 C28 H28 117.0 . . ?
C27 C28 H28 117.0 . . ?
C28 C29 C30 119(3) . . ?
C28 C29 H29 120.6 . . ?
C30 C29 H29 120.5 . . ?
C31 C30 C29 120(3) . . ?
C31 C30 H30 120.1 . . ?
C29 C30 H30 120.1 . . ?
C30 C31 C32 123(2) . . ?
C30 C31 H31 118.7 . . ?
C32 C31 H31 118.7 . . ?
C23 C32 C31 125(2) . . ?
C23 C32 C27 118(2) . . ?
C31 C32 C27 117(2) . . ?
C3 N1 C4 118(2) . . ?
C3 N1 Hg1 121.5(17) . . ?
C4 N1 Hg1 120.8(14) . . ?
C6 N2 C7 118(2) . . ?
C20 N3 C19 119(2) . . ?
C20 N3 Hg2 117.5(16) . . ?
C19 N3 Hg2 122.9(15) . . ?
C22 N4 C23 124(2) . . ?
N1 Hg1 N1 96.4(8) . 2 ?
N1 Hg1 Br1 95.9(5) . 2 ?
N1 Hg1 Br1 101.1(5) 2 2 ?
N1 Hg1 Br1 101.1(5) . . ?
N1 Hg1 Br1 95.9(5) 2 . ?
Br1 Hg1 Br1 154.30(14) 2 . ?
N3 Hg2 N3 99.5(9) 2_556 . ?
N3 Hg2 Br2 100.1(4) 2_556 2_556 ?
N3 Hg2 Br2 97.2(4) . 2_556 ?
N3 Hg2 Br2 97.2(4) 2_556 . ?
N3 Hg2 Br2 100.1(4) . . ?
Br2 Hg2 Br2 152.98(13) 2_556 . ?

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
C5 C1 C2 C3 -2(4) . . . . ?
C1 C2 C3 N1 3(4) . . . . ?
C2 C1 C5 C4 4(4) . . . . ?
C2 C1 C5 C6 -179(3) . . . . ?
N1 C4 C5 C1 -7(3) . . . . ?
N1 C4 C5 C6 175.6(19) . . . . ?
C1 C5 C6 N2 12(4) . . . . ?
C4 C5 C6 N2 -171(2) . . . . ?
N2 C7 C8 C9 -173(2) . . . . ?
C16 C7 C8 C9 -6(4) . . . . ?
C7 C8 C9 C10 4(4) . . . . ?
C8 C9 C10 C11 -3(4) . . . . ?
C8 C9 C10 Cl1 179.9(19) . . . . ?
C9 C10 C11 C16 4(4) . . . . ?
Cl1 C10 C11 C16 -178(2) . . . . ?
C9 C10 C11 C12 177(2) . . . . ?
Cl1 C10 C11 C12 -6(3) . . . . ?
C16 C11 C12 C13 -5(4) . . . . ?
C10 C11 C12 C13 -178(2) . . . . ?
C11 C12 C13 C14 1(4) . . . . ?
C12 C13 C14 C15 1(4) . . . . ?
C13 C14 C15 C16 1(4) . . . . ?
C10 C11 C16 C15 -180(2) . . . . ?
C12 C11 C16 C15 8(4) . . . . ?
C10 C11 C16 C7 -6(3) . . . . ?
C12 C11 C16 C7 -179(2) . . . . ?
C14 C15 C16 C11 -6(4) . . . . ?
C14 C15 C16 C7 -179(2) . . . . ?
C8 C7 C16 C11 7(3) . . . . ?
N2 C7 C16 C11 175(2) . . . . ?
C8 C7 C16 C15 -180(2) . . . . ?
N2 C7 C16 C15 -12(3) . . . . ?
C21 C17 C18 C19 -8(3) . . . . ?
C17 C18 C19 N3 7(4) . . . . ?
N3 C20 C21 C17 -4(3) . . . . ?
N3 C20 C21 C22 -177(2) . . . . ?
C18 C17 C21 C20 7(3) . . . . ?
C18 C17 C21 C22 -179(2) . . . . ?
C20 C21 C22 N4 163(2) . . . . ?
C17 C21 C22 N4 -10(3) . . . . ?
N4 C23 C24 C25 179.1(19) . . . . ?
C32 C23 C24 C25 4(3) . . . . ?
C23 C24 C25 C26 -6(3) . . . . ?
C24 C25 C26 C27 5(3) . . . . ?
C24 C25 C26 Cl2 -177.3(17) . . . . ?
C25 C26 C27 C28 -176(2) . . . . ?
Cl2 C26 C27 C28 7(4) . . . . ?
C25 C26 C27 C32 -3(3) . . . . ?
Cl2 C26 C27 C32 179.4(17) . . . . ?
C26 C27 C28 C29 176(2) . . . . ?
C32 C27 C28 C29 4(4) . . . . ?
C27 C28 C29 C30 -2(4) . . . . ?
C28 C29 C30 C31 1(4) . . . . ?
C29 C30 C31 C32 -1(4) . . . . ?
N4 C23 C32 C31 1(3) . . . . ?
C24 C23 C32 C31 177(2) . . . . ?
N4 C23 C32 C27 -177.4(19) . . . . ?
C24 C23 C32 C27 -2(3) . . . . ?
C30 C31 C32 C23 -176(3) . . . . ?
C30 C31 C32 C27 3(4) . . . . ?
C28 C27 C32 C23 175(2) . . . . ?
C26 C27 C32 C23 1(3) . . . . ?
C28 C27 C32 C31 -4(3) . . . . ?
C26 C27 C32 C31 -177(2) . . . . ?
C2 C3 N1 C4 -6(3) . . . . ?
C2 C3 N1 Hg1 170.4(17) . . . . ?
C5 C4 N1 C3 8(3) . . . . ?
C5 C4 N1 Hg1 -168.2(14) . . . . ?
C5 C6 N2 C7 168(2) . . . . ?
C8 C7 N2 C6 -39(4) . . . . ?
C16 C7 N2 C6 153(2) . . . . ?
C21 C20 N3 C19 2(3) . . . . ?
C21 C20 N3 Hg2 174.2(16) . . . . ?
C18 C19 N3 C20 -3(3) . . . . ?
C18 C19 N3 Hg2 -175.5(17) . . . . ?
C21 C22 N4 C23 -173(2) . . . . ?
C24 C23 N4 C22 28(4) . . . . ?
C32 C23 N4 C22 -157(2) . . . . ?
C3 N1 Hg1 N1 -96.7(17) . . . 2 ?
C4 N1 Hg1 N1 79.8(15) . . . 2 ?
C3 N1 Hg1 Br1 5.3(17) . . . 2 ?
C4 N1 Hg1 Br1 -178.3(15) . . . 2 ?
C3 N1 Hg1 Br1 166.0(16) . . . . ?
C4 N1 Hg1 Br1 -17.6(16) . . . . ?
C20 N3 Hg2 N3 -75.2(15) . . . 2_556 ?
C19 N3 Hg2 N3 97.2(18) . . . 2_556 ?
C20 N3 Hg2 Br2 -176.8(15) . . . 2_556 ?
C19 N3 Hg2 Br2 -4.4(18) . . . 2_556 ?
C20 N3 Hg2 Br2 23.9(16) . . . . ?
C19 N3 Hg2 Br2 -163.7(17) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        26.99
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         1.012
_refine_diff_density_min         -1.100
_refine_diff_density_rms         0.196
####################################################################### 
# 
# 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_d
_database_code_depnum_ccdc_archive 'CCDC 1471194'
_audit_update_record             
;
2016-03-29 deposited with the CCDC.
2016-06-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H22 Br4 Hg1 N4'
_chemical_formula_weight         982.73

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   31.332(7)
_cell_length_b                   5.3491(15)
_cell_length_c                   25.909(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 135.818(11)
_cell_angle_gamma                90.00
_cell_volume                     3026.3(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    13687
_cell_measurement_theta_min      1.59
_cell_measurement_theta_max      27.00

_exptl_crystal_description       Needle
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.157
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1848
_exptl_absorpt_coefficient_mu    10.397
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.1524
_exptl_absorpt_correction_T_max  0.6012
_exptl_absorpt_process_details   'shape of crystal determined optically'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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  'STOE IPDS II'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean '0.15 mm'
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13687
_diffrn_reflns_av_R_equivalents  0.0985
_diffrn_reflns_av_sigmaI/netI    0.0854
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         1.59
_diffrn_reflns_theta_max         27.00
_reflns_number_total             3305
_reflns_number_gt                3150
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_cell_refinement       'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_data_reduction        'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0528P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3305
_refine_ls_number_parameters     186
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0812
_refine_ls_R_factor_gt           0.0702
_refine_ls_wR_factor_ref         0.1621
_refine_ls_wR_factor_gt          0.1366
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.002

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 0.6640(9) 1.208(3) 0.4340(12) 0.055(5) Uani 1 1 d . . .
H1 H 0.6916 1.3374 0.4635 0.066 Uiso 1 1 calc R . .
C2 C 0.6657(9) 1.074(3) 0.3910(11) 0.064(6) Uani 1 1 d . . .
H2 H 0.6960 1.1066 0.3930 0.077 Uiso 1 1 calc R . .
C3 C 0.6226(10) 0.888(3) 0.3440(12) 0.059(6) Uani 1 1 d . . .
H3 H 0.6240 0.8062 0.3135 0.071 Uiso 1 1 calc R . .
C4 C 0.5796(8) 0.948(3) 0.3836(11) 0.046(5) Uani 1 1 d . . .
H4 H 0.5500 0.9050 0.3822 0.056 Uiso 1 1 calc R . .
C5 C 0.6207(9) 1.148(3) 0.4332(9) 0.039(4) Uani 1 1 d . . .
C6 C 0.6115(9) 1.286(3) 0.4722(10) 0.047(5) Uani 1 1 d . . .
H6 H 0.5850 1.2287 0.4747 0.057 Uiso 1 1 calc R . .
C7 C 0.6289(9) 1.641(3) 0.5383(10) 0.048(5) Uani 1 1 d . . .
C8 C 0.5754(9) 1.634(3) 0.5177(12) 0.054(5) Uani 1 1 d . . .
H8 H 0.5445 1.5243 0.4809 0.065 Uiso 1 1 calc R . .
C9 C 0.5671(9) 1.794(3) 0.5528(11) 0.048(5) Uani 1 1 d . . .
H9 H 0.5305 1.7848 0.5393 0.057 Uiso 1 1 calc R . .
C10 C 0.6082(7) 1.954(3) 0.6033(9) 0.038(4) Uani 1 1 d . . .
C11 C 0.6648(8) 1.979(3) 0.6259(9) 0.039(4) Uani 1 1 d . . .
C12 C 0.7124(9) 2.152(3) 0.6794(10) 0.045(5) Uani 1 1 d . . .
H12 H 0.7067 2.2630 0.7017 0.054 Uiso 1 1 calc R . .
C13 C 0.7653(10) 2.161(3) 0.6986(11) 0.058(6) Uani 1 1 d . . .
H13 H 0.7958 2.2728 0.7350 0.069 Uiso 1 1 calc R . .
C14 C 0.7745(9) 2.003(4) 0.6640(11) 0.062(5) Uani 1 1 d . . .
H14 H 0.8107 2.0135 0.6765 0.074 Uiso 1 1 calc R . .
C15 C 0.7303(8) 1.832(3) 0.6118(11) 0.046(5) Uani 1 1 d . . .
H15 H 0.7369 1.7271 0.5894 0.056 Uiso 1 1 calc R . .
C16 C 0.6739(8) 1.814(3) 0.5916(10) 0.040(4) Uani 1 1 d . . .
N1 N 0.5796(7) 0.821(2) 0.3403(8) 0.044(4) Uani 1 1 d . . .
N2 N 0.6411(6) 1.492(3) 0.5035(8) 0.048(4) Uani 1 1 d . . .
Hg1 Hg 0.5000 0.52323(17) 0.2500 0.0469(4) Uani 1 2 d S . .
Br1 Br 0.54011(10) 0.3994(3) 0.19832(12) 0.0592(6) Uani 1 1 d . . .
Br2 Br 0.59315(11) 2.1653(4) 0.64888(13) 0.0652(7) 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
C1 C2 1.36(3) . ?
C1 C5 1.38(2) . ?
C1 H1 0.9300 . ?
C2 C3 1.39(3) . ?
C2 H2 0.9300 . ?
C3 N1 1.33(2) . ?
C3 H3 0.9300 . ?
C4 N1 1.31(2) . ?
C4 C5 1.44(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.44(2) . ?
C6 N2 1.29(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.35(2) . ?
C7 C16 1.40(2) . ?
C7 N2 1.44(2) . ?
C8 C9 1.40(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.30(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.42(2) . ?
C10 Br2 1.919(18) . ?
C11 C16 1.42(2) . ?
C11 C12 1.43(2) . ?
C12 C13 1.35(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.41(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.38(2) . ?
C14 H14 0.9300 . ?
C15 C16 1.44(2) . ?
C15 H15 0.9300 . ?
N1 Hg1 2.421(14) . ?
Hg1 N1 2.421(14) 2_655 ?
Hg1 Br1 2.495(2) 2_655 ?
Hg1 Br1 2.495(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
C2 C1 C5 118.9(17) . . ?
C2 C1 H1 120.6 . . ?
C5 C1 H1 120.6 . . ?
C1 C2 C3 121(2) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 H2 119.6 . . ?
N1 C3 C2 123.5(19) . . ?
N1 C3 H3 118.3 . . ?
C2 C3 H3 118.3 . . ?
N1 C4 C5 126.8(15) . . ?
N1 C4 H4 116.6 . . ?
C5 C4 H4 116.6 . . ?
C1 C5 C6 124.2(16) . . ?
C1 C5 C4 115.1(15) . . ?
C6 C5 C4 120.4(17) . . ?
N2 C6 C5 117.8(17) . . ?
N2 C6 H6 121.1 . . ?
C5 C6 H6 121.1 . . ?
C8 C7 C16 119.8(18) . . ?
C8 C7 N2 123.3(17) . . ?
C16 C7 N2 116.7(17) . . ?
C7 C8 C9 118.9(18) . . ?
C7 C8 H8 120.6 . . ?
C9 C8 H8 120.6 . . ?
C10 C9 C8 123.1(19) . . ?
C10 C9 H9 118.5 . . ?
C8 C9 H9 118.5 . . ?
C9 C10 C11 121.3(17) . . ?
C9 C10 Br2 120.3(14) . . ?
C11 C10 Br2 118.4(12) . . ?
C10 C11 C16 115.9(15) . . ?
C10 C11 C12 126.0(16) . . ?
C16 C11 C12 118.1(16) . . ?
C13 C12 C11 122.4(17) . . ?
C13 C12 H12 118.8 . . ?
C11 C12 H12 118.8 . . ?
C12 C13 C14 120.2(18) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C15 C14 C13 120.3(18) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C14 C15 C16 120.5(16) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C7 C16 C11 121.1(16) . . ?
C7 C16 C15 120.5(17) . . ?
C11 C16 C15 118.4(15) . . ?
C4 N1 C3 114.8(15) . . ?
C4 N1 Hg1 122.4(12) . . ?
C3 N1 Hg1 122.3(12) . . ?
C6 N2 C7 118.1(15) . . ?
N1 Hg1 N1 97.7(6) . 2_655 ?
N1 Hg1 Br1 102.8(4) . 2_655 ?
N1 Hg1 Br1 97.3(4) 2_655 2_655 ?
N1 Hg1 Br1 97.3(4) . . ?
N1 Hg1 Br1 102.8(4) 2_655 . ?
Br1 Hg1 Br1 149.21(10) 2_655 . ?

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
C5 C1 C2 C3 3(3) . . . . ?
C1 C2 C3 N1 -3(3) . . . . ?
C2 C1 C5 C6 -175.6(17) . . . . ?
C2 C1 C5 C4 -2(3) . . . . ?
N1 C4 C5 C1 0(3) . . . . ?
N1 C4 C5 C6 174.1(16) . . . . ?
C1 C5 C6 N2 7(3) . . . . ?
C4 C5 C6 N2 -166.2(16) . . . . ?
C16 C7 C8 C9 -3(3) . . . . ?
N2 C7 C8 C9 -177.1(15) . . . . ?
C7 C8 C9 C10 2(3) . . . . ?
C8 C9 C10 C11 1(3) . . . . ?
C8 C9 C10 Br2 -179.7(13) . . . . ?
C9 C10 C11 C16 -2(2) . . . . ?
Br2 C10 C11 C16 178.5(11) . . . . ?
C9 C10 C11 C12 178.4(16) . . . . ?
Br2 C10 C11 C12 -1(2) . . . . ?
C10 C11 C12 C13 178.8(16) . . . . ?
C16 C11 C12 C13 -1(2) . . . . ?
C11 C12 C13 C14 2(3) . . . . ?
C12 C13 C14 C15 -2(3) . . . . ?
C13 C14 C15 C16 0(3) . . . . ?
C8 C7 C16 C11 2(2) . . . . ?
N2 C7 C16 C11 176.3(13) . . . . ?
C8 C7 C16 C15 -177.2(16) . . . . ?
N2 C7 C16 C15 -2(2) . . . . ?
C10 C11 C16 C7 1(2) . . . . ?
C12 C11 C16 C7 -179.5(15) . . . . ?
C10 C11 C16 C15 179.5(14) . . . . ?
C12 C11 C16 C15 -1(2) . . . . ?
C14 C15 C16 C7 179.8(16) . . . . ?
C14 C15 C16 C11 1(2) . . . . ?
C5 C4 N1 C3 0(2) . . . . ?
C5 C4 N1 Hg1 -172.7(13) . . . . ?
C2 C3 N1 C4 2(3) . . . . ?
C2 C3 N1 Hg1 174.4(14) . . . . ?
C5 C6 N2 C7 175.7(14) . . . . ?
C8 C7 N2 C6 -26(2) . . . . ?
C16 C7 N2 C6 159.5(15) . . . . ?
C4 N1 Hg1 N1 74.8(12) . . . 2_655 ?
C3 N1 Hg1 N1 -97.4(14) . . . 2_655 ?
C4 N1 Hg1 Br1 -24.5(13) . . . 2_655 ?
C3 N1 Hg1 Br1 163.2(13) . . . 2_655 ?
C4 N1 Hg1 Br1 178.9(12) . . . . ?
C3 N1 Hg1 Br1 6.7(13) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         1.200
_refine_diff_density_min         -1.201
_refine_diff_density_rms         0.242
