# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2015

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

data_1
_database_code_depnum_ccdc_archive 'CCDC 1404358'
_audit_update_record             
;
2015-06-02 deposited with the CCDC.
2015-09-01 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 H18 Br2 Hg N4 O2'
_chemical_formula_weight         658.75

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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pbcn

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

_cell_length_a                   12.5435(3)
_cell_length_b                   9.6560(2)
_cell_length_c                   16.5414(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2003.50(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4786
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      28.29

_exptl_crystal_description       column
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.184
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1232
_exptl_absorpt_coefficient_mu    11.687
_exptl_absorpt_correction_type   multi_scan
_exptl_absorpt_correction_T_min  0.0893
_exptl_absorpt_correction_T_max  0.3878
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS, 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10302
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_av_sigmaI/netI    0.0325
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.46
_diffrn_reflns_theta_max         28.29
_reflns_number_total             2479
_reflns_number_gt                1719
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS, 2010)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2010)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'

_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)+(0.0493P)²+0.0789P] 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         2479
_refine_ls_number_parameters     114
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0551
_refine_ls_R_factor_gt           0.0326
_refine_ls_wR_factor_ref         0.0882
_refine_ls_wR_factor_gt          0.0784
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Hg Hg 0.5000 0.16603(2) 0.7500 0.03290(11) Uani 1 2 d S . .
Br Br 0.68750(5) 0.09484(10) 0.74111(3) 0.0773(3) Uani 1 1 d . . .
O O 0.2176(2) 0.3576(3) 0.9820(2) 0.0419(8) Uani 1 1 d . . .
N1 N 0.4941(2) 0.3602(4) 0.8458(3) 0.0329(9) Uani 1 1 d . . .
N2 N 0.2984(2) 0.5638(3) 0.96122(18) 0.0276(7) Uani 1 1 d . . .
H2A H 0.2915 0.6513 0.9696 0.033 Uiso 1 1 calc R . .
C1 C 0.5722(3) 0.4526(5) 0.8407(3) 0.0419(11) Uani 1 1 d . . .
H1A H 0.6351 0.4275 0.8148 0.050 Uiso 1 1 calc R . .
C2 C 0.5638(4) 0.5834(5) 0.8719(3) 0.0491(13) Uani 1 1 d . . .
H2B H 0.6196 0.6462 0.8667 0.059 Uiso 1 1 calc R . .
C3 C 0.4705(4) 0.6205(5) 0.9114(3) 0.0437(12) Uani 1 1 d . . .
H3A H 0.4624 0.7092 0.9325 0.052 Uiso 1 1 calc R . .
C4 C 0.3893(3) 0.5235(4) 0.9190(2) 0.0251(8) Uani 1 1 d . . .
C5 C 0.4039(3) 0.3948(4) 0.8840(2) 0.0286(9) Uani 1 1 d . . .
H5A H 0.3491 0.3302 0.8870 0.034 Uiso 1 1 calc R . .
C6 C 0.2195(3) 0.4830(4) 0.9907(2) 0.0285(10) Uani 1 1 d . . .
C7 C 0.1377(3) 0.5580(4) 1.0411(2) 0.0322(9) Uani 1 1 d . . .
H7A H 0.1316 0.6523 1.0216 0.039 Uiso 1 1 calc R . .
H7B H 0.1630 0.5621 1.0965 0.039 Uiso 1 1 calc R . .
C8 C 0.0283(3) 0.4920(5) 1.0404(3) 0.0312(10) Uani 1 1 d . . .
H8A H -0.0149 0.5338 1.0825 0.047 Uiso 1 1 calc R . .
H8B H 0.0354 0.3942 1.0527 0.047 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Hg 0.02987(16) 0.03354(16) 0.03529(16) 0.000 0.00622(9) 0.000
Br 0.0509(4) 0.1184(7) 0.0626(4) 0.0231(3) 0.0136(3) 0.0477(4)
O 0.0385(19) 0.0170(14) 0.070(2) -0.0063(14) 0.0166(15) -0.0025(13)
N1 0.028(2) 0.034(2) 0.036(2) -0.0068(17) 0.0052(15) -0.0026(16)
N2 0.0261(19) 0.0175(16) 0.0391(19) -0.0044(15) 0.0065(15) 0.0010(14)
C1 0.026(2) 0.053(3) 0.047(3) -0.010(2) 0.004(2) -0.009(2)
C2 0.032(3) 0.050(3) 0.066(3) -0.020(3) 0.013(2) -0.015(2)
C3 0.038(3) 0.032(2) 0.061(3) -0.016(3) 0.007(2) -0.012(2)
C4 0.023(2) 0.024(2) 0.028(2) -0.0021(16) 0.0010(16) -0.0001(17)
C5 0.024(2) 0.028(2) 0.034(2) -0.0016(18) 0.0060(17) -0.0045(18)
C6 0.024(2) 0.026(2) 0.035(2) -0.0012(19) -0.0008(17) 0.0040(17)
C7 0.029(2) 0.029(2) 0.038(2) -0.006(2) 0.0051(18) -0.0003(19)
C8 0.029(2) 0.032(2) 0.033(2) 0.003(2) 0.0111(18) 0.0012(18)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Hg Br 2.4547(6) 3_656 ?
Hg Br 2.4547(6) . ?
Hg N1 2.456(4) 3_656 ?
Hg N1 2.456(4) . ?
O C6 1.220(4) . ?
N1 C1 1.328(5) . ?
N1 C5 1.337(5) . ?
N2 C6 1.350(5) . ?
N2 C4 1.393(4) . ?
N2 H2A 0.8600 . ?
C1 C2 1.368(6) . ?
C1 H1A 0.9300 . ?
C2 C3 1.388(7) . ?
C2 H2B 0.9300 . ?
C3 C4 1.389(6) . ?
C3 H3A 0.9300 . ?
C4 C5 1.383(5) . ?
C5 H5A 0.9300 . ?
C6 C7 1.507(5) . ?
C7 C8 1.513(6) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C8 1.522(8) 5_567 ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?

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
Br Hg Br 147.47(5) 3_656 . ?
Br Hg N1 106.35(7) 3_656 3_656 ?
Br Hg N1 98.39(7) . 3_656 ?
Br Hg N1 98.39(7) 3_656 . ?
Br Hg N1 106.35(7) . . ?
N1 Hg N1 80.5(2) 3_656 . ?
C1 N1 C5 119.1(4) . . ?
C1 N1 Hg 116.7(3) . . ?
C5 N1 Hg 121.4(3) . . ?
C6 N2 C4 128.2(3) . . ?
C6 N2 H2A 115.9 . . ?
C4 N2 H2A 115.9 . . ?
N1 C1 C2 122.7(4) . . ?
N1 C1 H1A 118.7 . . ?
C2 C1 H1A 118.7 . . ?
C1 C2 C3 118.8(4) . . ?
C1 C2 H2B 120.6 . . ?
C3 C2 H2B 120.6 . . ?
C2 C3 C4 119.1(4) . . ?
C2 C3 H3A 120.5 . . ?
C4 C3 H3A 120.5 . . ?
C5 C4 C3 118.1(4) . . ?
C5 C4 N2 124.7(3) . . ?
C3 C4 N2 117.2(3) . . ?
N1 C5 C4 122.3(4) . . ?
N1 C5 H5A 118.8 . . ?
C4 C5 H5A 118.8 . . ?
O C6 N2 123.1(4) . . ?
O C6 C7 121.9(4) . . ?
N2 C6 C7 114.9(3) . . ?
C6 C7 C8 114.3(3) . . ?
C6 C7 H7A 108.7 . . ?
C8 C7 H7A 108.7 . . ?
C6 C7 H7B 108.7 . . ?
C8 C7 H7B 108.7 . . ?
H7A C7 H7B 107.6 . . ?
C7 C8 C8 112.8(4) . 5_567 ?
C7 C8 H8A 109.0 . . ?
C8 C8 H8A 109.0 5_567 . ?
C7 C8 H8B 109.0 . . ?
C8 C8 H8B 109.0 5_567 . ?
H8A C8 H8B 107.8 . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        28.29
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         1.232
_refine_diff_density_min         -1.746
_refine_diff_density_rms         0.171
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2
_database_code_depnum_ccdc_archive 'CCDC 1404359'
_audit_update_record             
;
2015-06-02 deposited with the CCDC.
2015-09-01 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 H18 Br2 Hg N4 O2'
_chemical_formula_weight         658.75

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'

_symmetry_cell_setting           Tetragonal
_symmetry_space_group_name_H-M   P4(3)2(1)2

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y+1/2, x+1/2, z+3/4'
'y+1/2, -x+1/2, z+1/4'
'-x+1/2, y+1/2, -z+3/4'
'x+1/2, -y+1/2, -z+1/4'
'y, x, -z'
'-y, -x, -z+1/2'

_cell_length_a                   8.45900(10)
_cell_length_b                   8.45900(10)
_cell_length_c                   27.3117(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1954.28(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4692
_cell_measurement_theta_min      3.29
_cell_measurement_theta_max      28.17

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.239
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1232
_exptl_absorpt_coefficient_mu    11.982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.1235
_exptl_absorpt_correction_T_max  0.3804
_exptl_absorpt_process_details   'sadabs v2008/1(bruker axs, 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10386
_diffrn_reflns_av_R_equivalents  0.0418
_diffrn_reflns_av_sigmaI/netI    0.0483
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_theta_min         2.52
_diffrn_reflns_theta_max         28.29
_reflns_number_total             2420
_reflns_number_gt                1987
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0201P)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   0.003(12)
_refine_ls_number_reflns         2420
_refine_ls_number_parameters     114
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0456
_refine_ls_R_factor_gt           0.0317
_refine_ls_wR_factor_ref         0.0585
_refine_ls_wR_factor_gt          0.0555
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Hg Hg 0.63409(2) 0.63409(2) 0.0000 0.04184(10) Uani 1 2 d S . .
Br Br 0.56538(8) 0.58457(7) 0.08670(2) 0.05583(17) Uani 1 1 d . . .
O O 0.5776(4) 1.1144(4) 0.13787(13) 0.0468(9) Uani 1 1 d . . .
N1 N 0.6573(4) 0.9228(5) 0.00157(17) 0.0389(9) Uani 1 1 d . . .
N2 N 0.7886(5) 1.2054(5) 0.09519(15) 0.0376(9) Uani 1 1 d . . .
H2A H 0.8750 1.2586 0.0974 0.045 Uiso 1 1 calc R . .
C1 C 0.6862(6) 0.9890(6) 0.0453(2) 0.0344(13) Uani 1 1 d . . .
H1A H 0.6626 0.9331 0.0737 0.041 Uiso 1 1 calc R . .
C2 C 0.7509(6) 1.1401(6) 0.04892(19) 0.0325(11) Uani 1 1 d . . .
C3 C 0.7826(6) 1.2218(6) 0.0067(2) 0.0397(11) Uani 1 1 d . . .
H3A H 0.8267 1.3224 0.0085 0.048 Uiso 1 1 calc R . .
C4 C 0.7502(7) 1.1574(7) -0.0377(2) 0.0455(15) Uani 1 1 d . . .
H4A H 0.7691 1.2134 -0.0664 0.055 Uiso 1 1 calc R . .
C5 C 0.6874(7) 1.0037(7) -0.0391(2) 0.0432(15) Uani 1 1 d . . .
H5A H 0.6664 0.9573 -0.0693 0.052 Uiso 1 1 calc R . .
C6 C 0.6995(7) 1.1909(6) 0.1364(2) 0.0391(13) Uani 1 1 d . . .
C7 C 0.7687(8) 1.2752(7) 0.1796(2) 0.0621(19) Uani 1 1 d . . .
H7A H 0.8829 1.2656 0.1783 0.075 Uiso 1 1 calc R . .
H7B H 0.7430 1.3867 0.1771 0.075 Uiso 1 1 calc R . .
C8 C 0.7131(7) 1.2159(8) 0.2277(2) 0.0598(18) Uani 1 1 d . . .
H8A H 0.7319 1.1028 0.2287 0.072 Uiso 1 1 calc R . .
H8B H 0.5996 1.2315 0.2293 0.072 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Hg 0.04702(11) 0.04702(11) 0.03150(15) -0.00318(12) 0.00318(12) -0.00272(14)
Br 0.0726(4) 0.0612(4) 0.0337(3) 0.0057(3) 0.0090(3) -0.0060(3)
O 0.049(2) 0.055(2) 0.036(2) -0.007(2) 0.0025(18) -0.008(2)
N1 0.045(2) 0.043(2) 0.029(2) -0.006(2) 0.002(3) 0.0010(17)
N2 0.038(2) 0.044(3) 0.031(2) -0.005(2) -0.002(2) -0.0039(18)
C1 0.046(3) 0.030(3) 0.027(3) 0.001(2) 0.002(2) 0.000(2)
C2 0.033(3) 0.036(3) 0.028(3) -0.001(3) -0.006(2) 0.007(2)
C3 0.046(3) 0.033(3) 0.039(3) 0.003(3) 0.005(3) -0.002(2)
C4 0.061(4) 0.041(3) 0.034(3) 0.012(3) 0.007(3) 0.008(3)
C5 0.054(4) 0.050(3) 0.026(3) -0.002(3) -0.004(3) 0.002(3)
C6 0.060(3) 0.034(3) 0.022(3) -0.004(2) -0.007(3) 0.010(3)
C7 0.097(5) 0.056(4) 0.033(3) -0.002(3) -0.012(3) -0.026(4)
C8 0.062(4) 0.095(5) 0.022(3) -0.014(3) 0.001(3) -0.014(4)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Hg N1 2.451(4) 7 ?
Hg N1 2.451(4) . ?
Hg Br 2.4739(6) 7 ?
Hg Br 2.4739(6) . ?
O C6 1.219(6) . ?
N1 C5 1.330(7) . ?
N1 C1 1.341(6) . ?
N2 C6 1.360(7) . ?
N2 C2 1.415(6) . ?
N2 H2A 0.8600 . ?
C1 C2 1.394(7) . ?
C1 H1A 0.9300 . ?
C2 C3 1.371(7) . ?
C3 C4 1.357(7) . ?
C3 H3A 0.9300 . ?
C4 C5 1.405(8) . ?
C4 H4A 0.9300 . ?
C5 H5A 0.9300 . ?
C6 C7 1.497(8) . ?
C7 C8 1.483(9) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C8 1.487(11) 8_775 ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?

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 Hg N1 80.85(18) 7 . ?
N1 Hg Br 99.83(11) 7 7 ?
N1 Hg Br 105.34(11) . 7 ?
N1 Hg Br 105.34(11) 7 . ?
N1 Hg Br 99.83(11) . . ?
Br Hg Br 146.78(3) 7 . ?
C5 N1 C1 119.6(4) . . ?
C5 N1 Hg 120.9(4) . . ?
C1 N1 Hg 116.5(3) . . ?
C6 N2 C2 125.4(5) . . ?
C6 N2 H2A 117.3 . . ?
C2 N2 H2A 117.3 . . ?
N1 C1 C2 121.2(5) . . ?
N1 C1 H1A 119.4 . . ?
C2 C1 H1A 119.4 . . ?
C3 C2 C1 118.6(5) . . ?
C3 C2 N2 120.7(5) . . ?
C1 C2 N2 120.6(5) . . ?
C4 C3 C2 120.7(5) . . ?
C4 C3 H3A 119.7 . . ?
C2 C3 H3A 119.7 . . ?
C3 C4 C5 118.2(5) . . ?
C3 C4 H4A 120.9 . . ?
C5 C4 H4A 120.9 . . ?
N1 C5 C4 121.7(5) . . ?
N1 C5 H5A 119.2 . . ?
C4 C5 H5A 119.2 . . ?
O C6 N2 123.0(5) . . ?
O C6 C7 123.9(5) . . ?
N2 C6 C7 113.1(5) . . ?
C8 C7 C6 114.4(5) . . ?
C8 C7 H7A 108.7 . . ?
C6 C7 H7A 108.7 . . ?
C8 C7 H7B 108.7 . . ?
C6 C7 H7B 108.7 . . ?
H7A C7 H7B 107.6 . . ?
C7 C8 C8 117.5(6) . 8_775 ?
C7 C8 H8A 107.9 . . ?
C8 C8 H8A 107.9 8_775 . ?
C7 C8 H8B 107.9 . . ?
C8 C8 H8B 107.9 8_775 . ?
H8A C8 H8B 107.2 . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        28.29
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.427
_refine_diff_density_min         -0.737
_refine_diff_density_rms         0.120
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_3
_database_code_depnum_ccdc_archive 'CCDC 1404360'
_audit_update_record             
;
2015-06-02 deposited with the CCDC.
2015-09-01 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 H18 Hg I2 N4 O2'
_chemical_formula_weight         752.73

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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Hg Hg -2.3894 9.2266 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pnma

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

_cell_length_a                   9.69190(10)
_cell_length_b                   16.6752(2)
_cell_length_c                   12.9961(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2100.36(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8075
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      28.28

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.380
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1376
_exptl_absorpt_coefficient_mu    10.284
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.1831
_exptl_absorpt_correction_T_max  0.3076
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS, 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19183
_diffrn_reflns_av_R_equivalents  0.0434
_diffrn_reflns_av_sigmaI/netI    0.0344
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.99
_diffrn_reflns_theta_max         28.30
_reflns_number_total             2703
_reflns_number_gt                1951
_reflns_threshold_expression     >2sigma(I)


_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS, 2010)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2010)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'

_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)+(0.0363P)²+4.6792P] 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         2703
_refine_ls_number_parameters     130
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0534
_refine_ls_R_factor_gt           0.0321
_refine_ls_wR_factor_ref         0.0858
_refine_ls_wR_factor_gt          0.0768
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Hg Hg 0.17807(3) 0.7500 0.49721(2) 0.03597(11) Uani 1 2 d S . .
I1 I 0.047(2) 0.7500 0.3215(9) 0.085(2) Uani 0.50 2 d SP . .
I1' I 0.075(2) 0.7500 0.3132(9) 0.095(4) Uani 0.50 2 d SP . .
I2 I 0.1455(6) 0.7500 0.7009(4) 0.0519(8) Uani 0.50 2 d SP . .
I2' I 0.1211(7) 0.7500 0.6947(5) 0.0874(19) Uani 0.50 2 d SP . .
O O 0.3640(4) 0.5171(3) 0.2120(3) 0.0556(11) Uani 1 1 d . . .
N1 N 0.3682(5) 0.6514(3) 0.4840(3) 0.0396(11) Uani 1 1 d . . .
N2 N 0.5690(5) 0.5386(3) 0.2892(3) 0.0416(11) Uani 1 1 d . . .
H2A H 0.6567 0.5334 0.2810 0.050 Uiso 1 1 calc R . .
C1 C 0.4526(7) 0.6480(4) 0.5619(4) 0.0562(17) Uani 1 1 d . . .
H1A H 0.4264 0.6706 0.6243 0.067 Uiso 1 1 calc R . .
C2 C 0.5827(8) 0.6107(4) 0.5538(5) 0.063(2) Uani 1 1 d . . .
H2B H 0.6425 0.6089 0.6097 0.076 Uiso 1 1 calc R . .
C3 C 0.6179(7) 0.5780(4) 0.4629(5) 0.0543(16) Uani 1 1 d . . .
H3A H 0.7045 0.5548 0.4552 0.065 Uiso 1 1 calc R . .
C4 C 0.5281(6) 0.5784(3) 0.3815(4) 0.0386(12) Uani 1 1 d . . .
C5 C 0.4052(6) 0.6182(3) 0.3933(4) 0.0418(14) Uani 1 1 d . . .
H5A H 0.3457 0.6224 0.3374 0.050 Uiso 1 1 calc R . .
C6 C 0.4919(5) 0.5081(3) 0.2136(4) 0.0344(12) Uani 1 1 d . . .
C7 C 0.5664(7) 0.4619(4) 0.1338(4) 0.0479(15) Uani 1 1 d . . .
H7A H 0.5768 0.4071 0.1575 0.057 Uiso 1 1 calc R . .
H7B H 0.6582 0.4844 0.1261 0.057 Uiso 1 1 calc R . .
C8 C 0.4962(6) 0.4606(3) 0.0273(4) 0.0406(13) Uani 1 1 d . . .
H8A H 0.5397 0.4199 -0.0149 0.049 Uiso 1 1 calc R . .
H8B H 0.4000 0.4459 0.0358 0.049 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Hg 0.03403(19) 0.04129(16) 0.03258(15) 0.000 0.00163(13) 0.000
I1 0.121(4) 0.0498(19) 0.084(4) 0.000 -0.066(3) 0.000
I1' 0.159(10) 0.067(2) 0.0585(18) 0.000 -0.062(3) 0.000
I2 0.0547(11) 0.0735(19) 0.0273(11) 0.000 0.0130(8) 0.000
I2' 0.144(5) 0.063(2) 0.055(2) 0.000 0.050(3) 0.000
O 0.025(2) 0.091(3) 0.051(2) -0.018(2) -0.002(2) 0.006(2)
N1 0.039(3) 0.040(2) 0.040(3) -0.0018(18) -0.003(2) 0.007(2)
N2 0.026(2) 0.058(3) 0.041(2) -0.005(2) 0.000(2) 0.006(2)
C1 0.064(5) 0.067(4) 0.038(3) -0.015(3) -0.009(3) 0.020(4)
C2 0.060(5) 0.084(5) 0.045(3) -0.019(3) -0.023(3) 0.024(4)
C3 0.042(4) 0.069(4) 0.053(3) -0.015(3) -0.010(3) 0.013(3)
C4 0.035(3) 0.046(3) 0.035(3) -0.004(2) -0.001(2) 0.006(3)
C5 0.041(3) 0.049(3) 0.036(3) 0.000(2) 0.000(2) 0.007(3)
C6 0.022(3) 0.053(3) 0.028(2) -0.003(2) 0.001(2) -0.004(2)
C7 0.039(4) 0.059(4) 0.045(3) -0.009(3) 0.008(3) 0.007(3)
C8 0.032(3) 0.045(3) 0.045(3) -0.011(2) 0.003(3) -0.002(3)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Hg N1 2.475(5) 7_575 ?
Hg N1 2.475(5) . ?
Hg I1' 2.590(9) . ?
Hg I1 2.615(10) . ?
Hg I2' 2.625(7) . ?
Hg I2 2.666(6) . ?
O C6 1.249(6) . ?
N1 C1 1.303(7) . ?
N1 C5 1.350(6) . ?
N2 C6 1.335(7) . ?
N2 C4 1.428(6) . ?
N2 H2A 0.8600 . ?
C1 C2 1.409(9) . ?
C1 H1A 0.9300 . ?
C2 C3 1.346(9) . ?
C2 H2B 0.9300 . ?
C3 C4 1.370(8) . ?
C3 H3A 0.9300 . ?
C4 C5 1.372(8) . ?
C5 H5A 0.9300 . ?
C6 C7 1.480(7) . ?
C7 C8 1.543(8) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C8 1.495(11) 5_665 ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?

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 Hg N1 83.2(2) 7_575 . ?
N1 Hg I1' 102.8(4) 7_575 . ?
N1 Hg I1' 102.8(4) . . ?
N1 Hg I1 107.6(3) 7_575 . ?
N1 Hg I1 107.6(3) . . ?
I1' Hg I1 6.6(9) . . ?
N1 Hg I2' 102.98(14) 7_575 . ?
N1 Hg I2' 102.98(14) . . ?
I1' Hg I2' 145.3(5) . . ?
I1 Hg I2' 138.7(5) . . ?
N1 Hg I2 99.04(13) 7_575 . ?
N1 Hg I2 99.04(13) . . ?
I1' Hg I2 150.6(5) . . ?
I1 Hg I2 144.0(5) . . ?
I2' Hg I2 5.3(2) . . ?
C1 N1 C5 119.5(5) . . ?
C1 N1 Hg 116.3(4) . . ?
C5 N1 Hg 122.0(4) . . ?
C6 N2 C4 129.8(5) . . ?
C6 N2 H2A 115.1 . . ?
C4 N2 H2A 115.1 . . ?
N1 C1 C2 121.6(5) . . ?
N1 C1 H1A 119.2 . . ?
C2 C1 H1A 119.2 . . ?
C3 C2 C1 118.1(6) . . ?
C3 C2 H2B 121.0 . . ?
C1 C2 H2B 121.0 . . ?
C2 C3 C4 121.0(6) . . ?
C2 C3 H3A 119.5 . . ?
C4 C3 H3A 119.5 . . ?
C3 C4 C5 117.8(5) . . ?
C3 C4 N2 118.0(5) . . ?
C5 C4 N2 124.1(5) . . ?
N1 C5 C4 121.8(5) . . ?
N1 C5 H5A 119.1 . . ?
C4 C5 H5A 119.1 . . ?
O C6 N2 121.4(5) . . ?
O C6 C7 122.4(5) . . ?
N2 C6 C7 116.2(5) . . ?
C6 C7 C8 114.9(5) . . ?
C6 C7 H7A 108.6 . . ?
C8 C7 H7A 108.6 . . ?
C6 C7 H7B 108.6 . . ?
C8 C7 H7B 108.6 . . ?
H7A C7 H7B 107.5 . . ?
C8 C8 C7 113.0(6) 5_665 . ?
C8 C8 H8A 109.0 5_665 . ?
C7 C8 H8A 109.0 . . ?
C8 C8 H8B 109.0 5_665 . ?
C7 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        28.30
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         1.040
_refine_diff_density_min         -0.890
_refine_diff_density_rms         0.141
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_4
_database_code_depnum_ccdc_archive 'CCDC 1404361'
_audit_update_record             
;
2015-06-02 deposited with the CCDC.
2015-09-01 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 H18 Hg I2 N4 O2'
_chemical_formula_weight         752.73

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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Hg Hg -2.3894 9.2266 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Tetragonal
_symmetry_space_group_name_H-M   P4(3)2(1)2

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y+1/2, x+1/2, z+3/4'
'y+1/2, -x+1/2, z+1/4'
'-x+1/2, y+1/2, -z+3/4'
'x+1/2, -y+1/2, -z+1/4'
'y, x, -z'
'-y, -x, -z+1/2'

_cell_length_a                   8.57840(10)
_cell_length_b                   8.57840(10)
_cell_length_c                   27.9769(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2058.79(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7344
_cell_measurement_theta_min      2.48
_cell_measurement_theta_max      27.79

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.429
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1376
_exptl_absorpt_coefficient_mu    10.491
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4872
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS, 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19750
_diffrn_reflns_av_R_equivalents  0.0612
_diffrn_reflns_av_sigmaI/netI    0.0483
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_theta_min         2.48
_diffrn_reflns_theta_max         28.30
_reflns_number_total             2567
_reflns_number_gt                1923
_reflns_threshold_expression     >2sigma(I)


_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS, 2010)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2010)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'

_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)+(0.0126P)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   -0.009(7)
_refine_ls_number_reflns         2567
_refine_ls_number_parameters     114
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0527
_refine_ls_R_factor_gt           0.0291
_refine_ls_wR_factor_ref         0.0512
_refine_ls_wR_factor_gt          0.0461
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_restrained_S_all      1.004
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Hg Hg 0.84655(3) 0.84655(3) 0.0000 0.04209(10) Uani 1 2 d S . .
I I 0.91975(5) 0.90903(5) 0.089641(11) 0.05229(13) Uani 1 1 d . . .
O O 0.9050(5) 0.3821(5) 0.13916(12) 0.0485(11) Uani 1 1 d . . .
N1 N 0.8266(5) 0.5620(5) 0.00483(14) 0.0430(11) Uani 1 1 d . . .
N2 N 0.6962(5) 0.2919(5) 0.09835(12) 0.0387(11) Uani 1 1 d . . .
H2A H 0.6110 0.2396 0.1007 0.046 Uiso 1 1 calc R . .
C1 C 0.7943(7) 0.4979(7) 0.04779(16) 0.0370(14) Uani 1 1 d . . .
H1A H 0.8142 0.5562 0.0751 0.044 Uiso 1 1 calc R . .
C2 C 0.7338(6) 0.3516(7) 0.05300(16) 0.0332(13) Uani 1 1 d . . .
C3 C 0.7065(7) 0.2640(7) 0.01252(16) 0.0411(14) Uani 1 1 d . . .
H3A H 0.6638 0.1646 0.0148 0.049 Uiso 1 1 calc R . .
C4 C 0.7437(7) 0.3268(7) -0.03161(18) 0.0456(17) Uani 1 1 d . . .
H4A H 0.7293 0.2689 -0.0594 0.055 Uiso 1 1 calc R . .
C5 C 0.8018(7) 0.4750(8) -0.03390(17) 0.0458(17) Uani 1 1 d . . .
H5A H 0.8250 0.5169 -0.0637 0.055 Uiso 1 1 calc R . .
C6 C 0.7818(7) 0.3092(7) 0.13853(17) 0.0376(15) Uani 1 1 d . . .
C7 C 0.7167(8) 0.2292(8) 0.18203(18) 0.058(2) Uani 1 1 d . . .
H7A H 0.6039 0.2372 0.1813 0.070 Uiso 1 1 calc R . .
H7B H 0.7434 0.1195 0.1806 0.070 Uiso 1 1 calc R . .
C8 C 0.7741(7) 0.2943(8) 0.22823(17) 0.058(2) Uani 1 1 d . . .
H8A H 0.8862 0.2804 0.2296 0.069 Uiso 1 1 calc R . .
H8B H 0.7537 0.4055 0.2285 0.069 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Hg 0.04856(14) 0.04856(14) 0.02914(12) 0.00272(11) -0.00272(11) -0.00243(17)
I 0.0694(3) 0.0547(3) 0.03281(16) -0.00548(18) -0.00837(19) -0.0044(2)
O 0.051(3) 0.060(3) 0.0340(18) 0.0067(19) -0.0026(19) -0.003(2)
N1 0.061(3) 0.039(3) 0.030(2) 0.004(2) -0.007(2) 0.001(2)
N2 0.045(3) 0.035(3) 0.036(2) 0.007(2) 0.008(2) 0.001(2)
C1 0.052(4) 0.033(4) 0.026(2) 0.003(2) -0.002(2) -0.004(3)
C2 0.030(3) 0.042(4) 0.028(2) 0.001(2) 0.002(2) 0.006(3)
C3 0.047(4) 0.035(4) 0.041(3) -0.003(2) -0.009(2) 0.004(3)
C4 0.066(5) 0.040(4) 0.031(3) -0.007(3) -0.007(3) 0.004(3)
C5 0.061(5) 0.051(4) 0.025(2) 0.001(3) 0.000(3) 0.009(4)
C6 0.047(4) 0.039(4) 0.027(3) -0.002(2) 0.003(3) 0.005(3)
C7 0.077(5) 0.061(5) 0.036(3) 0.006(3) 0.010(3) -0.005(4)
C8 0.057(4) 0.088(5) 0.028(3) 0.013(3) 0.000(3) -0.010(4)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Hg N1 2.451(4) 7 ?
Hg N1 2.451(4) . ?
Hg I 2.6402(3) 7 ?
Hg I 2.6403(3) . ?
O C6 1.228(6) . ?
N1 C5 1.333(6) . ?
N1 C1 1.350(6) . ?
N2 C6 1.351(6) . ?
N2 C2 1.406(6) . ?
N2 H2A 0.8600 . ?
C1 C2 1.366(8) . ?
C1 H1A 0.9300 . ?
C2 C3 1.379(7) . ?
C3 C4 1.384(7) . ?
C3 H3A 0.9300 . ?
C4 C5 1.367(8) . ?
C4 H4A 0.9300 . ?
C5 H5A 0.9300 . ?
C6 C7 1.504(7) . ?
C7 C8 1.492(8) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C8 1.473(10) 8_665 ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?

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 Hg N1 82.2(2) 7 . ?
N1 Hg I 99.58(9) 7 7 ?
N1 Hg I 107.67(9) . 7 ?
N1 Hg I 107.67(9) 7 . ?
N1 Hg I 99.58(9) . . ?
I Hg I 143.67(2) 7 . ?
C5 N1 C1 117.6(5) . . ?
C5 N1 Hg 121.6(3) . . ?
C1 N1 Hg 118.0(3) . . ?
C6 N2 C2 125.9(5) . . ?
C6 N2 H2A 117.1 . . ?
C2 N2 H2A 117.1 . . ?
N1 C1 C2 123.1(5) . . ?
N1 C1 H1A 118.4 . . ?
C2 C1 H1A 118.4 . . ?
C1 C2 C3 118.5(5) . . ?
C1 C2 N2 121.2(4) . . ?
C3 C2 N2 120.2(5) . . ?
C2 C3 C4 118.8(5) . . ?
C2 C3 H3A 120.6 . . ?
C4 C3 H3A 120.6 . . ?
C5 C4 C3 119.2(5) . . ?
C5 C4 H4A 120.4 . . ?
C3 C4 H4A 120.4 . . ?
N1 C5 C4 122.7(5) . . ?
N1 C5 H5A 118.6 . . ?
C4 C5 H5A 118.6 . . ?
O C6 N2 122.4(5) . . ?
O C6 C7 122.7(5) . . ?
N2 C6 C7 114.9(5) . . ?
C8 C7 C6 114.1(5) . . ?
C8 C7 H7A 108.7 . . ?
C6 C7 H7A 108.7 . . ?
C8 C7 H7B 108.7 . . ?
C6 C7 H7B 108.7 . . ?
H7A C7 H7B 107.6 . . ?
C8 C8 C7 115.9(6) 8_665 . ?
C8 C8 H8A 108.3 8_665 . ?
C7 C8 H8A 108.3 . . ?
C8 C8 H8B 108.3 8_665 . ?
C7 C8 H8B 108.3 . . ?
H8A C8 H8B 107.4 . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        28.30
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.569
_refine_diff_density_min         -0.873
_refine_diff_density_rms         0.124


#===END

